Luminescent compounds

Abstract

To provide a series of luminescent compounds for use in labeling biomolecules, such as antibodies, that can covalently bind specifically to a molecule of interest, that do not require excitation at phototoxic wavelengths, and that can be excited at the same or similar wavelengths but emit at different wavelengths.SOLUTION: The luminescent compounds are represented by the general formula in the figure.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates generally to luminescent compounds. More specifically, but not exclusively, the present invention relates to luminescent compounds capable of forming covalent bonds with a second species, such as a biomolecule, for use as a chemical or biosensor.

[0002] Fluorescent dyes are frequently used as labels, for example, cell and tissue labels. Such dyes can be used in a wide range of biological applications, such as immunofluorescence assays, flow cytometry, fluorescence microscopy, Western blots, and cell imaging.

[0003] Some of the most common fluorescent dyes include xanthene derivatives such as fluorescein, eosin, rhodamine, Oregan green (RTM), and Texas red (RTM). Many other families of organic fluorophores are known.

[0004] One of the most widely used classes of fluorescent dyes is the Alexa Fluor (RTM) series, designed by Molecular Probes and currently sold by ThermoFisher Scientific (Waltham, Massachusetts, United States). The Alexa Fluor (RTM) series includes over 20 different fluorescent dyes that exhibit emission spectra spanning the near-UV, visible, and near-IR spectral ranges.

[0005] It is known to conjugate a fluorescent dye to a biomolecule or species of interest by forming a covalent bond between the fluorescent dye and the biomolecule. For example, it is known to conjugate a fluorescent dye to an antibody. This can be used to track the conjugated antibody and visualize its interaction with a specific antigen. Typically, the fluorescent dye forms a covalent bond to the biomolecule via a functional group located on the fluorescent dye, such as a thiol-reactive or amine-reactive functional group.

[0006] Fluorescent dyes often require excitation wavelengths in the UV or near-UV spectral range, which can cause phototoxicity. It would be advantageous to provide fluorescent dyes that do not require excitation at phototoxic wavelengths.

[0007] It is known to use fluorescent dyes in multiplex assay systems. A multiplex assay is the combination of assays for many target analytes in a single reaction volume. This reduces workflow and sample volume issues. It is known to use a combination of different fluorescent dyes to detect different analytes. However, in many cases, different dyes require different excitation wavelengths, which adds complexity to the system.

[0008] It would be advantageous to provide a series of luminescent compounds for use in labeling molecules, e.g., biomolecules such as antibodies, that can be excited at the same or similar wavelengths but emit at different wavelengths.

[0009] Accordingly, a first aspect of the invention is a light-emitting compound represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; p is an integer of 1 or 2, q and s are independently integers 1, 2, 3, or 4; Y 1 , Y 2 , and Y 3 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a halogen atom (e.g., fluorine, chlorine, bromine atom), a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , and / or Y 3 two or more of may combine together to form a fused ring (e.g., a fused aromatic ring), Y 1 , Y 2 , and / or Y 3 wherein one or more of the following comprises a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0010] In embodiments, the second species can be a small molecule and / or a biomolecule. For example, the biomolecule can be an amino acid, a peptide, a protein, a nucleic acid, a polynucleotide, or an antibody. In embodiments, the second species is a therapeutic species or a pharmaceutically active molecule, e.g., a drug molecule.

[0011] Advantageously, the luminescent compounds of the invention can be covalently attached to a second species that is capable of specifically binding to a molecule of interest, and can therefore be used as chemical or biosensors.

[0012] Applicants define a biosensor as a sensor that includes or consists of a luminescent compound that can be used to detect or determine the concentration of a chemical or biological substance.

[0013] Additionally or alternatively, the second species can be a solid support, for example, for use in solid phase synthesis. Additionally or alternatively, the second species can be a nanoparticle, for example, a nanoparticle comprising or formed from a metal or metal alloy, carbon, clay, polymer, and / or ceramic material.

[0014] In an embodiment, X represents an oxygen atom. In an embodiment, X represents a sulfur atom.

[0015] Y 1 , Y 2 , and / or Y 3 One or more of the spacing portions comprises a continuous chain of 3 to 20 atoms, e.g., 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, e.g., 9 atoms. The atoms may be selected from carbon atoms or combinations of carbon atoms and heteroatoms, e.g., oxygen atoms and / or nitrogen atoms.

[0016] When referring to a continuous chain of spacing moieties with a continuous chain of 3 to 20 atoms, Applicant means that the carbon atoms or combinations of carbon atoms and heteroatoms of the uninterrupted linear chain of 3 to 20 atoms are covalently bonded to form the backbone. The carbon atoms and / or heteroatoms (forming the backbone of the spacing moieties) may have other atoms attached or bonded to them that are not included as part of the definition of a continuous chain of 3 to 20 atoms, such as hydrogen atoms, branched alkyl groups, or aryl groups.

[0017] It is understood that the spacing moiety and the functional group are different moieties and their definitions do not overlap, i.e., the functional group is different from the continuous chain of 3-20 atoms of the spacing moiety.

[0018] In embodiments, the continuous chain of spacing moieties may include one continuous chain of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0019] Y 1 , Y 2 , and / or Y 3 One or more spacing moieties of Y may comprise or consist of a polyether chain covalently attached to a functional group capable of forming a covalent bond with a second species. For example, Y 1 , Y 2 , and / or Y 3 may comprise or consist of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. 1 , Y 2 , and / or Y 3 The continuous chain of one or more of the spacing portions may comprise or consist of a polyether chain having a continuous chain of 9 atoms selected from carbon and oxygen.

[0020] In embodiments, a functional group (FG) capable of forming a covalent bond with a second species may be located at the terminus of the spacing moiety.

[0021] In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2CH2- moiety. In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with a second species is selected from the group consisting of Y 1 , Y 2 , and / or Y 3 may be located at the termini of the spacing moiety, such as consisting of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0022] In embodiments, the light-emitting compound is a triphenylene derivative, i.e., the light-emitting compound comprises a triphenylene core. In embodiments, the light-emitting compound comprises a core comprising a polycyclic aromatic hydrocarbon, for example, comprising 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 or more fused six-membered rings. For example, the light-emitting compound may comprise a core comprising a polycyclic aromatic hydrocarbon comprising six fused six-membered rings.

[0023] In embodiments, the light-emitting compound is represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 two or more of may combine together to form a fused ring (e.g., a fused aromatic ring), Y4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 one or more of the following include a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0024] Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 One or more of the spacing portions comprises a continuous chain of 3 to 20 atoms, e.g., 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, e.g., 9 atoms. The atoms may be carbon atoms or a combination of carbon atoms and heteroatoms, e.g., oxygen atoms and / or nitrogen atoms.

[0025] In embodiments, the continuous chain of spacing moieties may include one continuous chain of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13One or more spacing moieties of Y may comprise or consist of a polyether chain covalently attached to a functional group capable of forming a covalent bond with a second species. For example, Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 may comprise or consist of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 The continuous chain of one or more of the spacing portions may comprise or consist of a polyether chain having a continuous chain of 9 atoms selected from carbon and oxygen.

[0026] In embodiments, a functional group (FG) capable of forming a covalent bond with a second species may be located at either end or at a specific end of the spacing portion.

[0027] In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2CH2- moiety. In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with a second species is selected from the group consisting of Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13may be located at the termini of the spacing moiety, such as consisting of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0028] In the luminescent compound of the invention, Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 One or more of Y contains a spacing moiety and a functional group as defined above. 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 The remainder of Y may be free of such spacing moieties and / or functional groups. 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 A single one of Y may contain a spacing moiety and a functional group, while the rest will not. 12 comprises a spacing moiety and a functional group, and Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 13 does not include spacing moieties and functional groups.

[0029] Y 1 ~Y 3 , or Y 4 ~Y 13If one or more of, or all but one of, does not contain a spacing moiety and a functional group, then Y 1 ~Y 13 may represent or include an alkyl group. The alkyl group(s) may be straight or linear chain, or may include branched chains, and / or may be further functionalized. Additionally or alternatively, Y 1 ~Y 3 , or Y 4 ~Y 13 may independently represent or include an aryl group. The aryl group(s) may be unsubstituted or further functionalized. In embodiments, Y 4 ~Y 13 can independently represent or include a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain can contain a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0030] In an embodiment, Y 1 ~Y 3 , or Y 4 ~Y 13 may independently represent or include an alkoxy group, e.g., an OR' group, where R' is a straight or branched chain alkyl. The alkyl chain may contain 1 to 20 carbon atoms, e.g., 2 to 18 carbon atoms, 3 to 17 carbon atoms, 4 to 16 carbon atoms, 5 to 15 carbon atoms, 6 to 14 carbon atoms, 7 to 13 carbon atoms, 8 to 12 carbon atoms, or 9 to 11 carbon atoms.

[0031] In an embodiment, Y 1 ~Y 3 One or more of, for example, all but one, or Y 4 ~Y 13All but one of the following are examples: OCH3, OC2H5, OC3H7, OC4H9, OC5H 11、 OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or OC 10 H 21 The alkoxy group may comprise or consist of a linear alkoxy group selected from one or more of the following groups:

[0032] In an embodiment, Y 5 , Y 6 , Y 9 , Y 10 , Y 13 Each represents a hydrogen atom.

[0033] In an embodiment, Y 4 , Y 7 , Y 8 , Y 11 Each represents an OR' group. OR' groups include OCH3, OC2H5, OC3H7, OC4H9, and OC5H 11 , OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or O.C. 10 H 21 For example, Y 4 , Y 7 , Y 8 , Y 11 are OC5H respectively. 11 It may represent a group.

[0034] In an embodiment, Y 12 represents a spacing moiety and a functional group capable of forming a covalent bond with a second species. For example, Y 12 may represent a -O-(CH2CH2O)2CH2CH2FG moiety or a -O-(CH2CH2O)2CH2FG moiety, where FG is a functional group capable of forming a covalent bond with a second species.

[0035] For example, in embodiments, X represents an oxygen atom, and / or Y 5 , Y6 , Y 9 , Y 10 , Y 13 each represents a hydrogen atom, and Y 4 , Y 7 , Y 8 , Y 11 are each an OR' group (e.g., OC5H 11 group), and Y 12 represents the -O-(CH2CH2O)2CH2CH2FG moiety.

[0036] In an embodiment, Y 8 represents an oxygen atom, and Y 9 represents a nitrogen atom, and Y 8 and Y 9 are linked to form an oxazole moiety containing R groups selected from aromatic and / or aliphatic groups.

[0037] In embodiments, the light-emitting compound is represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R 1 and R 2 independently represent an aromatic group and / or an aliphatic group; p and q are independently an integer of 1 to 2; s is an integer from 1 to 4, Y 1 , Y 2 , and Y 3 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , or Y3 two or more of may combine together to form a fused ring (e.g., a fused aromatic ring), Y 1 , Y 2 , Y 3 one or more of the following include a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0038] In embodiments containing two or more X atoms, preferably the X atoms are one of the same type of heteroatom, ie, nitrogen, oxygen, sulfur, phosphorus, or selenium atoms.

[0039] In an embodiment, Y 6 represents an oxygen atom, and Y 7 represents a nitrogen atom, and Y 6 and Y 7 are linked to form an oxazole moiety with R groups selected from aromatic and / or aliphatic groups. Additionally or alternatively, Y 11 represents an oxygen atom, and Y 10 represents a nitrogen atom, and Y 11 and Y 10 are linked to form an oxazole moiety with an R group selected from an aromatic group and / or an aliphatic group. In embodiments, the light-emitting compound includes one, two, or three oxazole moieties.

[0040] In embodiments, the light-emitting compound is represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R 1 , R 2 , R 3 independently represent an aromatic group and / or an aliphatic group; p, q, and s are each independently an integer of 1 to 2; Y 1 , Y 2 , and Y 3 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , Y 3 one or more of the following include a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0041] Preferably, R 1 , R 2 , R 3 represents the same type of group, for example, R 1 , R 2 , R 3 may each represent a naphthalene group.

[0042] In an embodiment, Y 5 and Y 6 represents carbon atoms that combine together to form a fused ring, for example a fused aromatic ring, fused to the core of the light-emitting compound.

[0043] In embodiments, the light-emitting compound may be represented by the following general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R independently represents an aromatic group and / or an aliphatic group; q is independently an integer from 1 to 3; s is independently an integer from 1 to 4; t is independently an integer from 1 to 4; Y 2 , Y 3 , and Y 14 and J independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group containing a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 2 , Y 3 , and / or Y 14 two or more of may combine together to form a fused ring (e.g., a fused aromatic ring), Y 2 , Y 3 , Y 14 and / or one or more of J comprises a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0044] Y 2 , Y 3 , Y 14 and / or one or more spacing portions of J comprise a continuous chain of 3 to 20 atoms, e.g., 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, e.g., 9 atoms. The atoms may be carbon atoms or combinations of carbon atoms and heteroatoms, e.g., oxygen atoms and / or nitrogen atoms.

[0045] In embodiments, the continuous chain of spacing moieties may include one continuous chain of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0046] Y 2 , Y 3 , Y 14 and / or one or more spacing moieties of J may comprise or consist of a polyether chain covalently attached to a functional group capable of forming a covalent bond with a second species. For example, Y 2 , Y 3 , Y 14 , and / or one or more spacing moieties of J may comprise or consist of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. 2 , Y 3 , Y 14 and / or the continuous chain of one or more of the spacing portions of J may comprise or consist of a polyether chain having a continuous chain of 9 atoms selected from carbon and oxygen.

[0047] In embodiments, a functional group (FG) capable of forming a covalent bond with a second species may be located at either end or at a specific end of the spacing portion.

[0048] In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2CH2- moiety. In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with a second species is selected from the group consisting of Y 2 , Y 3 , Y 14 , and / or one or more of J may be located at the termini of the spacing moiety, such as consisting of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0049] In embodiments, the light-emitting compound(s) may be represented by the following general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R independently represents an aromatic group and / or an aliphatic group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 independently comprise, consist of, or represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 two or more of which combine together to form a fused ring (e.g., a fused aromatic ring); Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y26 one or more of the following include a spacing portion comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second species, the functional group being selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or ketone), and / or an aliphatic alcohol.

[0050] Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 One or more of the spacing portions comprises a continuous chain of 3 to 20 atoms, e.g., 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, e.g., 9 atoms. The atoms may be carbon atoms or a combination of carbon atoms and heteroatoms, e.g., oxygen atoms and / or nitrogen atoms.

[0051] In embodiments, the continuous chain of spacing moieties may include one continuous chain of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0052] Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 One or more spacing moieties of Y may comprise or consist of a polyether chain covalently attached to a functional group capable of forming a covalent bond with a second species. For example, Y 15 , Y 16 , Y17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may comprise or consist of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 The continuous chain of one or more of the spacing portions may comprise or consist of a polyether chain having a continuous chain of 9 atoms selected from carbon and oxygen.

[0053] In embodiments, a functional group (FG) capable of forming a covalent bond with a second species may be located at the terminus of the spacing moiety.

[0054] In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2CH2- moiety. In embodiments, the spacing moiety may consist of a -O-(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with a second species is selected from the group consisting of Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26may be located at the termini of the spacing moiety, such as consisting of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0055] In an embodiment, Y 21 represents an oxygen atom, and Y 22 represents a nitrogen atom, and Y 21 and Y 22 are linked to form an oxazole moiety containing R groups selected from aromatic and / or aliphatic groups.

[0056] Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 If one or more of, or all but one of, does not contain a spacing moiety and a functional group, then Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may independently represent or include an alkyl group. The alkyl group(s) may be straight or linear chain, or may include branched chains, and / or may be further functionalized. Additionally or alternatively, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26may independently represent or include an aryl group. The aryl group(s) may be unsubstituted or further functionalized. In embodiments, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 can independently represent or include a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain can contain a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0057] In an embodiment, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may independently represent or include an alkoxy group, e.g., an OR' group, where R' is a straight or branched chain alkyl. The alkyl chain may contain 1 to 20 carbon atoms, e.g., 2 to 18 carbon atoms, 3 to 17 carbon atoms, 4 to 16 carbon atoms, 5 to 15 carbon atoms, 6 to 14 carbon atoms, 7 to 13 carbon atoms, 8 to 12 carbon atoms, or 9 to 11 carbon atoms.

[0058] In an embodiment, Y 15 , Y 16 , Y 17 , Y 18 , Y19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 One or more of, for example, all but one of, e.g., OCH3, OC2H5, OC3H7, OC4H9, OC5H 11、 OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or O.C. 10 H 21 The alkoxy group may include a straight chain alkoxy group selected from one or more of the groups.

[0059] In an embodiment, Y 16 , Y 19 , Y 22 , Y 23 , Y 26 Each represents a hydrogen atom.

[0060] In an embodiment, Y 15 , Y 17 , Y 18 , Y 20 , Y 21 , Y 24 , Y 25 Each represents an OR' group. For example, Y 15 , Y 20 , Y 21 , Y 24 , Y 25 are OC5H respectively. 11 For example, Y 17 , Y 18 may each represent an OCH group.

[0061] In an embodiment, Y 15 , Y 17 , Y 18 , Y 20 , Y 21 , Y 24 , Y 25 One or more of (e.g., Y 17 (only) represents the spacing moiety and functional group. For example, Y 17may represent the moiety -O-(CH2CH2O)2CH2CH2FG, where FG is a functional group capable of forming a covalent bond with a second species.

[0062] For example, in embodiments, X represents an oxygen atom and Y 16 , Y 19 , Y 22 , Y 23 , Y 26 each represents a hydrogen atom, and Y 15 , Y 20 , Y 21 , Y 24 , Y 25 are OC5H respectively. 11 represents a group, and Y 18 represents an OCH3 group, and Y 17 represents the -O-(CH2CH2O)2CH2CH2FG moiety.

[0063] A further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 1 , J 2 may combine together to form a fused ring (e.g., a fused aromatic ring), A 1 , A 2 , A 3, A 4 , A 5 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group; A 1 , A 2 , A 3 , A 4 , A 5 a light-emitting compound, wherein one or more of the following comprises a functional group capable of forming a covalent bond with a second species.

[0064] In embodiments, the functional groups may be selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or a ketone), and / or an aliphatic alcohol.

[0065] In an embodiment, J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom. 1 , J 2 , J 3 , J 4 , J 5 independently represent a deuterium atom.

[0066] In embodiments, R represents an aliphatic group or moiety. In embodiments, R represents an aromatic group or moiety.

[0067] In all embodiments, the term "fused ring" is intended to define groups that are joined together to form a ring (e.g., aromatic and / or heterocyclic ring) that forms part of the core of the light-emitting compound, i.e., groups that extend the triphenylene core.

[0068] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; J 5 , J 6 , J 7 , J 8 , J 9 , J 10 , J 11 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 6 and J 7 , or J 8 and J 9 may combine together to form a fused ring (e.g., a fused aromatic ring), A 6 , A 7 , A 8 , A 9 , A 10 , A 11 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group; A 6 , A 7 , A 8 , A 9 , A 10 , A 11 a light-emitting compound, wherein one or more of the following comprises a functional group capable of forming a covalent bond with a second species.

[0069] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R 1 and R 2 independently represent an aromatic group and / or an aliphatic group; J 12 , J 13 , J 14 , J 15 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 12 and J 13 may combine together to form a fused ring (e.g., a fused aromatic ring), A 12 , A 13 , A 14 , A 15 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group; A 12 , A 13 , A 14 , A 15 a light-emitting compound, wherein one or more of the following comprises a functional group capable of forming a covalent bond with a second species.

[0070] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R 1 , R 2 , R 3 independently represent an aromatic group and / or an aliphatic group; J 16 , J 17 , J 18independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; A 16 , A 17 , A 18 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group; A 16 , A 17 , A 18 a light-emitting compound, wherein one or more of the following comprises a functional group capable of forming a covalent bond with a second species.

[0071] The functional group capable of forming a covalent bond with a second species may be selected from one of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or a ketone), and / or an aliphatic alcohol.

[0072] In embodiments, A includes a functional group capable of forming a covalent bond with a second species. 1 , A 2 , A 3 , A 4 , A 5 One or more of the following, or A 6 , A 7 , A 8 , A 9 , A 10 , A 11 One or more of the following, or A 12 , A 13 , A 14 , A 15 One or more of the following, or A 16 , A 17 , A 18One or more of the may further comprise a spacing portion. The spacing portion may comprise a continuous chain of 3 to 20 atoms, e.g., 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, e.g., 9 atoms. The atoms may be selected from carbon atoms or combinations of carbon atoms and heteroatoms, e.g., oxygen atoms and / or nitrogen atoms.

[0073] In embodiments, the continuous chain of spacing moieties may include one continuous chain of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0074] A 1 , A 2 , A 3 , A 4 , A 5 One or more of the following, or A 6 , A 7 , A 8 , A 9 , A 10 , A 11 One or more of the following, or A 12 , A 13 , A 14 , A 15 One or more of the following, or A 16 , A 17 , A 18 One or more spacing moieties of A may comprise or consist of a polyether chain covalently attached to a functional group capable of forming a covalent bond with a second species. 1 ~A 18 The one or more spacing moieties of one or more of may comprise or consist of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms. 1 ~A 18 The continuous chain of one or more of the spacing portions may comprise or consist of a polyether chain having a continuous chain of 9 atoms selected from carbon and oxygen.

[0075] In embodiments, a functional group (FG) capable of forming a covalent bond with a second species may be located at the terminus of the spacing moiety. 1 ~A 18 One or more of may terminate in one of a carboxylic acid, ester, azide, amine, maleimide, thiol, isothiocyanate, carbonyl (e.g., aldehyde or ketone), and / or aliphatic alcohol.

[0076] In embodiments, the spacing moiety may consist of a -(CH2CH2O)2CH2CH2- moiety. In embodiments, the spacing moiety may consist of a -(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with a second species is A 1 , A 2 , A 3 , A 4 , A 5 One or more of the following, or A 6 , A 7 , A 8 , A 9 , A 10 , A 11 One or more of the following, or A 12 , A 13 , A 14 , A 15 One or more of the following, or A 16 , A 17 , A 18 may be located at the termini of the spacing moiety, such as consisting of -(CH2CH2O)2CH2CH2FG or -(CH2CH2O)2CH2FG.

[0077] A 1 , A 2 , A 3 , A 4 , A 5 One or more of, or all but one of, or A 6 , A 7 , A 8 , A 9 , A 10 , A 11 One or more of the following, or A 12 , A 13 , A 14, A 15 One or more of the following, or A 16 , A 17 , A 18 does not contain a spacing moiety and a functional group capable of forming a covalent bond with a second species, 1 ~A 18 One or more of A may comprise an alkyl group. The alkyl group(s) may be straight or linear chain, or may comprise branched chains, and / or may be further functionalized. Additionally or alternatively, A 1 ~A 18 can independently comprise an aryl group. The aryl group(s) can be unsubstituted or further functionalized.

[0078] In an embodiment, A 1 , A 2 , A 3 , A 4 , A 5 , or A 6 , A 7 , A 8 , A 9 , A 10 , A 11 , or A 12 , A 13 , A 14 , A 15 , or A 16 , A 17 , A 18 one or more of, for example, all but one of them, e.g., CH3, C2H5, C3H7, C4H9, C5H 11、 C6H 13 , C7H 15 , C8H 17 , C9H 19 , or C 10 H 21 The alkyl group may comprise or consist of a straight chain alkyl group independently selected from one or more of the alkyl groups.

[0079] In an embodiment, A 1 ~A 18may independently comprise a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain may comprise a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0080] The light-emitting compounds of the invention may include a single functional group capable of forming a covalent bond with a second species, i.e., a single functional group selected from a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl (e.g., an aldehyde or a ketone), and / or an aliphatic alcohol. In alternative embodiments, the light-emitting compounds may include two or more functional groups capable of forming a covalent bond with a second species. For example, A 1 ~A 18 Two or more of the functional groups may comprise a functional group capable of forming a covalent bond with a second species. In embodiments comprising two or more functional groups capable of forming a covalent bond with a second species, the functional groups may be selected to be the same or different types (i.e., a first type and a second type different from the first).

[0081] In embodiments, R, R 1 , R 2 , and / or R 3 may be an alkyl group, e.g., a straight or branched chain alkyl. In embodiments, R, R 1 , R 2 , R 3 At least one of the groups may be a methyl, ethyl, propyl, or butyl group.

[0082] R, R 1 , R 2 , and / or R 3 In embodiments where is an aromatic group, the aromatic group can be one or a combination of an aromatic hydrocarbon group and / or an aromatic heterocyclic group.

[0083] R, R 1 , R 2 , and / or R 3 In embodiments where is an aromatic hydrocarbon group, the aromatic hydrocarbon group may include one or a combination of phenyl and / or substituted phenyl rings. There may be one, two, three, four, or five additional substituents on the phenyl ring. The substituents are directly attached to the phenyl ring and may be one or a combination of fluorine, chlorine, bromine, iodine, hydroxyl groups, amine groups, nitro groups, alkoxy groups, carboxylic acids, amides, cyano groups, trifluoromethyl groups, esters, alkenes, alkynes, azides, azo groups, isocyanates, ketones, aldehydes, alkyl groups consisting of hydrocarbon chains or hydrocarbon rings, and alkyl groups consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen, and / or sulfur. The alkyl groups may include, for example, hydroxyl groups, amine groups, nitro groups, ether groups, carboxylic acids, amides, cyano groups, trifluoromethyl groups, esters, alkenes, alkynes, azides, azo groups, isocyanates, ketones, and aldehydes. The substituent may be another aromatic group, for example, R may comprise a phenyl substituted with an additional phenyl ring. In embodiments, the R group may be a phenyl ring substituted with a second phenyl ring, which in turn may be substituted with a third phenyl ring. In embodiments, R, R 1 , R 2 , or R 3 may represent a p-fluorophenyl group, an m-fluorophenyl group, an o-fluorophenyl group, a thiophene group, a cyanophenyl moiety (e.g., a p-cyanophenyl moiety), a trifluoromethylphenyl moiety (e.g., a p-trifluoromethylphenyl moiety), an iodophenyl moiety (e.g., an o-iodophenyl moiety), a chlorophenyl moiety (e.g., an o-chlorophenyl moiety), a bromophenyl moiety (e.g., an o-bromophenyl moiety), an aminophenyl moiety (e.g., a mono-, di-, or tri-substituted aminophenyl moiety), a nitrophenyl moiety (e.g., a p-nitrophenyl moiety), or a phenol moiety.

[0084] R, R 1 , R 2 , and / or R 3 In embodiments where R, R are aromatic groups, the aromatic groups can be polycyclic aromatic hydrocarbons, such as naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene, and / or benzo[c]fluorene. 1 , R 2 , and / or R 3 The group can be attached to the triphenylene derivative by any isomer of the polycyclic aromatic hydrocarbon described, for example, 1-naphthalene, 2-naphthalene, 2-anthracene, 9-anthracene. The polycyclic aromatic hydrocarbon group can be substituted with other moieties, such as aryl groups, alkyl groups, heteroatoms, and / or other electron-withdrawing or electron-donating groups.

[0085] In embodiments, R, R 1 , R 2 , and / or R 3 is naphthalene.

[0086] R, R 1 , R 2 , and / or R 3 In embodiments where is an aromatic heterocyclic group, the heterocyclic group can be a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring, a 8-membered ring, a 9-membered ring, a 10-membered ring, or a fused ring. In embodiments, the heterocyclic group can be furan, benzofuran, isobenzofuran, pyrrole, indole, isoindole, thiophene, benzothiophene, benzo[c]thiophene, imidazole, benzimidazole, purine, pyrazole, indazole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, pyridine, quinoline, isoquinoline, pyrazine, quinoxaline, acridine, pyrimidine, quinozoline, pyridazine, cinnoline, phthalazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, pyridine, or thiophene.

[0087] R, R 1 , R 2 , and / or R 3 In embodiments where is an aliphatic group, the aliphatic group may be one or a combination of an n-alkyl chain, a branched alkyl chain, an alkyl chain containing an unsaturated portion, or an alkyl chain containing a heteroatom, such as fluorine, chlorine, bromine, iodine, oxygen, sulfur, or nitrogen. The alkyl chain may contain an unsaturated portion including an alkene or an aromatic portion. The alkyl chain may contain a functional group for further derivatization of a polycyclic aromatic hydrocarbon, such as a triphenylene derivative. For example, the functional group may be one or more of an azide, a carbonyl group, an alcohol, a halogen, an alkene, or a thioacetate.

[0088] In embodiments, R, R 1 , R 2 , and / or R 3 includes crown ethers.

[0089] A still further aspect of the invention provides any one of the light-emitting compounds according to the invention covalently bonded to a second species.

[0090] In embodiments, the second species can be a small molecule and / or a biomolecule. For example, the second species can be an amino acid, a peptide, a protein, a nucleic acid, or a polynucleotide. The second species need not be a molecule. For example, the second species can be an antibody. In embodiments, the second species is a therapeutic species or a pharmaceutically active molecule, such as a drug molecule.

[0091] Advantageously, the luminescent molecules according to the invention are suitable for covalent binding to a second species, such as a biomolecule, or a small molecule, or a drug molecule, and therefore can be used as a biosensor.

[0092] The biomolecule can be an antibody, e.g., a monoclonal or polyclonal antibody. The biomolecule can be an avidin, e.g., streptavidin. The biomolecule can be biotin.

[0093] In embodiments, the second species may be a molecule for recognizing a species in a biological system. For example, the biomolecule may be capable of binding to a protein or receptor on the surface of a cell.

[0094] A still further aspect of the invention provides a biomolecule, such as an antibody, covalently attached to any of the light-emitting compounds of the invention.

[0095] A still further aspect of the invention provides a kit component suitable for use in covalently attaching any of the light-emitting compounds of the invention to a second species, such as a biomolecule, the kit component comprising one or more light-emitting compound(s) of the invention and a solvent suitable for dissolving or suspending the light-emitting compound(s). The solvent may include water, for example, the solvent may be an aqueous medium and / or a buffer solution. In embodiments, the solvent may include an organic solvent, for example, THF or DMSO, or a combination thereof. In embodiments, the solvent may include a first solvent that includes an aqueous medium and a second solvent that includes an organic solvent, for example, THF or DMSO, or a combination thereof.

[0096] In some embodiments, the kit components may further comprise a second species.

[0097] The kit components may further include a set of instructions describing how to covalently attach an inventive light-emitting compound to a second species.

[0098] The kit components may further include catalysts and / or coupling agents for use in covalently bonding the light-emitting compounds of the invention to a second species.

[0099] The kit components may further comprise measuring means, such as a pipette or pipette tip.The kit components may further comprise a container suitable for carrying out the reaction that covalently bonds the light-emitting compound to the second species.

[0100] A still further aspect of the invention provides a method of conjugating an inventive luminescent compound to a second species, the method comprising providing a luminescent molecule, providing the second species, and forming a covalent bond between the luminescent compound and the second species.

[0101] The method can include adding a second species, e.g., a solution or suspension of the second species, to a solution of the luminescent molecules.The method can include adding a solution of the luminescent molecules, e.g., a solution of the luminescent molecules, to a solution or suspension of the second species.

[0102] Advantageously, the luminescent compounds of the invention, when conjugated (i.e., covalently attached) to a second species, can be used, for example, in vivo, to locate and / or track the second species. The conjugated luminescent molecule and second species can also be used to locate and / or track a target species of the second species.

[0103] A still further aspect of the invention provides the use of one or more of the luminescent compounds according to the invention or conjugates thereof in a composition for cell or tissue imaging.

[0104] A conjugate of a luminescent molecule refers to a luminescent compound when covalently attached to a second species.

[0105] A still further aspect of the invention provides the use of a light-emitting compound or a conjugate thereof in immunofluorescence techniques.

[0106] A still further aspect of the invention provides the use of a light-emitting compound or a conjugate thereof in flow cytometry.

[0107] The luminescent species and their conjugates can be used, for example, in an assay to quantify and / or detect the presence of a second species or target. The luminescent species and their conjugates can be used to quantify and / or detect the presence of a biomolecule, such as DNA, RNA, a protein, a hormone, an antibody, or a cell. In this manner, the luminescent compounds and their conjugates can be used as biosensors.

[0108] The luminescent compounds according to the invention can be used to form a covalent bond with a second species present in vivo or in vitro. For example, a covalent bond between the luminescent compound and the second species can be formed in tissue culture, or cell culture, such as a plant, animal, or microbial cell culture.

[0109] The conjugate of the luminescent compound of the invention and a second species can be used in vivo, for example, to track or locate the second species in vivo, or to track or locate the target of the second species in vivo.The conjugate of the luminescent compound can be used, for example, to generate an image of the organ in which the conjugate accumulates.For example, images generated using fluorescent imaging techniques can be used to diagnose disease.

[0110] More advantageously, the light-emitting molecules of the invention are tunable. Surprisingly, it has been found that modifying the R group provides a series of light-emitting compounds that require the same excitation wavelength but exhibit different emission spectra. Even more advantageously, the light-emitting compounds of the invention can be designed to emit wavelengths across the entire visible spectrum by varying the structure of the R group.

[0111] In addition, the luminescent compounds of the invention can be used in multiplex systems. For example, two or more luminescent molecules according to the invention can be conjugated to each second species. The luminescent molecules can be excited at the same wavelength but emit at different wavelengths. This makes it possible to study two different second species, such as biomolecules, in, for example, a biological system using a single light source. For example, two or more different luminescent compounds according to the invention can be used to observe or track two different second species, such as biomolecules, in a system, for example, in vivo or ex vivo.

[0112] It has also been surprisingly discovered that the luminescent compounds of the invention may be usable in multiphoton excitation microscopy. As known in the art, in multiphoton microscopy (also known as two-photon microscopy), two or more photons of light are absorbed with each excitation. This technique differs from traditional fluorescence microscopy, in which the excitation wavelength is shorter than the emission wavelength. Two-photon excitation microscopy typically uses near-infrared excitation light. In some embodiments, multiphoton microscopy is performed by illuminating the luminescent compound, e.g., a conjugated luminescent compound, with a light source emitting wavelengths in the 500-1000 nm or 800-900 nm range. The use of multiphoton microscopy is advantageous because it uses lower energy light and is therefore less damaging to biological samples. Advantageously, this prevents or reduces phototoxicity when luminescent molecules are used in biological systems. More advantageously, the light penetrates tissue more deeply and is less likely to photobleach the luminescent compound.

[0113] The luminescent compound(s) may emit light in the visible spectrum, i.e., between 380 nm and 750 nm, and / or between 8000 cm -1 ~25,000cm -1 , e.g., 15,000 cm -1 ~25,000cm -1 In embodiments, the light-emitting compound(s) may exhibit a Stokes shift of 5.0×10 -13 Scm -1 , and 1.5 × 10-11 Scm -1 , e.g., 6 x 10 -12 Scm -1 ~1.5×10 -11 Scm -1 The luminescent compound(s) when illuminated at 350 nm may exhibit a conductivity value of 1.5×10 -10 Scm -1 ~1×10 -3 Scm -1 , e.g., 1 x 10 -8 Scm -1 ~1×10 -3 cm -1 It can exhibit a photoconductivity of

[0114] The light-emitting compound of the invention can be any of those shown in the examples of the invention, ie, any one of compounds 38-43 or a combination thereof.

[0115] Thus, a further aspect of the invention is a luminescent molecule represented by the general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; p is an integer of 1 or 2, q and s are independently integers 1, 2, 3, or 4; Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , and / or Y 3 can combine together to form a fused ring (eg, a fused aromatic ring), providing a light-emitting molecule.

[0116] In embodiments, the light-emitting compound is a triphenylene derivative, i.e., the light-emitting compound comprises a triphenylene core. In embodiments, the light-emitting compound comprises a core comprising a polycyclic aromatic hydrocarbon, for example, comprising 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 or more fused six-membered rings. For example, the light-emitting compound may comprise a core comprising a polycyclic aromatic hydrocarbon comprising six fused six-membered rings.

[0117] In embodiments, the emissive molecule is represented by the general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 Two or more of may combine together to form a fused ring (eg, a fused aromatic ring).

[0118] In an embodiment, Y 1~Y 13 One or more or all of may represent or include an alkyl group. The alkyl group(s) may be straight or linear chain, or may include branched chains, and / or may be further functionalized. The alkyl chain may include 1 to 20 carbon atoms, e.g., 2 to 18 carbon atoms, 3 to 17 carbon atoms, 4 to 16 carbon atoms, 5 to 15 carbon atoms, 6 to 14 carbon atoms, 7 to 13 carbon atoms, 8 to 12 carbon atoms, or 9 to 11 carbon atoms.

[0119] Additionally or alternatively, Y 1 ~Y 3 , or Y 4 ~Y 13 may independently represent or include an aryl group. The aryl group(s) may be unsubstituted or further functionalized. In embodiments, Y 1 ~Y 3 , or Y 4 ~Y 13 can independently represent or include a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain can contain a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0120] In an embodiment, Y 1 ~Y 3 , or Y 4 ~Y 13 may independently represent or include an alkoxy group, e.g., an OR′ group, where R′ is a straight or branched chain alkyl. 1 ~Y 3 , or Y 4 ~Y 13 One or more or all of the following may be, for example, OCH3, OC2H5, OC3H7, OC4H9, OC5H11、 OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or O.C. 10 H 21 It may comprise or consist of a straight chain alkoxy group selected from one or more of an alkyl group.

[0121] In an embodiment, Y 5 , Y 6 , Y 9 , Y 10 , Y 13 One or more or all of each represent a hydrogen atom.

[0122] In an embodiment, Y 4 , Y 7 , Y 8 , Y 11 , Y 12 Each represents an OR' group. For example, Y 4 , Y 7 , Y 8 , Y 11 are OC5H respectively. 11 It may represent a group.

[0123] In embodiments, the light-emitting compound is represented by the general formula: [ka] In the formula, R 1 and R 2 independently represent an aromatic group and / or an aliphatic group; p and q are independently an integer of 1 to 2; s is an integer from 1 to 4, Y 1 , Y 2 , and Y 3independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , or Y 3 may combine together to form a fused ring (eg, a fused aromatic ring).

[0124] In embodiments, the light-emitting compound is represented by the general formula: [ka] In the formula, R 1 , R 2 , R 3 independently represent an aromatic group and / or an aliphatic group; p, q, and s are each independently an integer of 1 to 2; Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group containing a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, or a nitro group.

[0125] Preferably, R 1 , R 2 , R 3 represents the same type of group, for example, R 1 , R 2 , R 3 may each represent a naphthalene group.

[0126] In embodiments, the light-emitting compound may be represented by the following general formula: [ka] wherein R independently represents an aromatic group and / or an aliphatic group; q is independently an integer from 1 to 3; s is independently an integer from 1 to 4; t is independently an integer from 1 to 4; Y 2 , Y 3 , Y 14 and J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group containing a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, or a nitro group; Y 2 , Y 3 , and / or Y 14 may combine together to form a fused ring (eg, a fused aromatic ring).

[0127] In embodiments, the light-emitting compound may be represented by the following general formula: [ka] wherein R independently represents an aromatic group and / or an aliphatic group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 Two or more of the following may be combined together to form a fused ring (eg, a fused aromatic ring).

[0128] In an embodiment, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may independently represent or include an alkyl group. The alkyl group(s) may be straight or linear chain, or may include branched chains, and / or may be further functionalized. Additionally or alternatively, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may independently represent or include an aryl group. The aryl group(s) may be unsubstituted or further functionalized. In embodiments, Y 15 , Y16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 can independently represent or include a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain can include a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0129] In an embodiment, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 may independently represent or include an alkoxy group, e.g., an OR' group, where R' is a straight or branched chain alkyl. The alkyl chain may contain 1 to 20 carbon atoms, e.g., 2 to 18 carbon atoms, 3 to 17 carbon atoms, 4 to 16 carbon atoms, 5 to 15 carbon atoms, 6 to 14 carbon atoms, 7 to 13 carbon atoms, 8 to 12 carbon atoms, or 9 to 11 carbon atoms.

[0130] In an embodiment, Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24, Y 25 , Y 26 One or more or all of the following may be, for example, OCH3, OC2H5, OC3H7, OC4H9, OC5H 11、 OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or O.C. 10 H 21 The alkyl groups may include straight chain alkoxy groups selected from one or more of the alkyl groups.

[0131] In an embodiment, Y 16 , Y 19 , Y 22 , Y 23 , Y 26 One or more or all of each represent a hydrogen atom.

[0132] In an embodiment, Y 15 , Y 17 , Y 18 , Y 20 , Y 21 , Y 24 , Y 25 One or more or all of each represent an OR' group. For example, Y 15 , Y 20 , Y 21 , Y 24 , Y 25 are OC5H respectively. 11 For example, Y 17 , Y 18 may each represent an OCH group.

[0133] For example, Y 16 , Y 19 , Y 22 , Y 23 , Y 26 each represents a hydrogen atom, and Y 15 , Y 20 , Y 21 , Y 24 , Y 25 are OC5H respectively. 11 represents a group, and Y 17 , Y 18 represents an OCH3 group.

[0134] A further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 1 and J 2 , or J 3 and J 4 may combine together to form a fused ring (e.g., a fused aromatic ring), A 1 , A 2 , A 3 , A 4 , A 5 independently represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

[0135] In all embodiments, the term "fused ring" is intended to define groups that are joined together to form a ring (e.g., aromatic and / or heterocyclic ring) that forms part of the core of the light-emitting compound, i.e., groups that extend the triphenylene core.

[0136] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; J 6 , J 7 , J 8 , J 9 , J 10 , J 11 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 6 and J 7 , and / or J 8 and J 9 may combine together to form a fused ring (e.g., a fused aromatic ring), A 6 , A 7 , A 8 , A 9 , A 10 , A 11 independently represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

[0137] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] In the formula, R 1 and R 2 independently represent an aromatic group and / or an aliphatic group; J 12 , J 13 , J 14 , J 15independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 12 and J 13 may combine together to form a fused ring (e.g., a fused aromatic ring), A 12 , A 13 , A 14 , A 15 independently represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

[0138] Yet a further aspect of the present invention is a light-emitting compound represented by the general formula: [ka] In the formula, R 1 , R 2 , R 3 independently represent an aromatic group and / or an aliphatic group; J independently represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, or a nitro group; A 16 , A 17 , A 18 independently represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

[0139] In an embodiment, A1 ~A 18 One or more or all of A may comprise an alkyl group. The alkyl group(s) may be straight or linear chain, or may comprise branched chains, and / or may be further functionalized. Additionally or alternatively, A 1 ~A 18 can independently comprise an aryl group. The aryl group(s) can be unsubstituted or further functionalized.

[0140] In an embodiment, A 1 ~A 18 One or more or all of the groups may be, for example, CH3, C2H5, C3H7, C4H9, C5H 11、 C6H 13 , C7H 15 , C8H 17 , C9H 19 , or C 10 H 21 The alkyl group may comprise or consist of a straight chain alkyl group selected from one or more of the alkyl groups.

[0141] In an embodiment, A 1 ~A 18 One or more or all of may independently comprise a polyether chain or a polyglycol group, e.g., a polyethylene glycol moiety. The polyether or polyglycol chain may comprise a total of 1 to 20 carbon and oxygen atoms, e.g., 2 to 18 carbon and oxygen atoms, 3 to 17 carbon and oxygen atoms, 4 to 16 carbon and oxygen atoms, 5 to 15 carbon and oxygen atoms, 6 to 14 carbon and oxygen atoms, 7 to 13 carbon and oxygen atoms, 8 to 12 carbon and oxygen atoms, or 9 to 11 carbon and oxygen atoms.

[0142] In embodiments, J, or J 1 ~J 15 One or more or all of may independently represent a hydrogen atom. In embodiments, A, or A 1 ~A 18One or more or all of A may independently represent a linear or branched alkyl group. 1 ~A 18 One or more or all of may independently represent a linear alkyl chain containing 1 to 20 carbon atoms, e.g., 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1 carbon atom. 1 ~A 18 one or more or all of may independently be CH3, C2H5, C3H7, C4H9, C5H 11 , C6H 13 , C7H 15 , C8H 17 , C9H 19 , and / or C 10 H 21 can be represented as:

[0143] For example, in an embodiment, J 1 , J 2 , J 3 , J 4 , J 5 each represents a hydrogen atom, and A 1 , A 2 , A 3 , A 4 , A 5 are each an alkyl chain, e.g., CH 11 Represents a part.

[0144] For example, in an embodiment, J 6 ~J 11 each represents a hydrogen atom, and A 6 ~A 11 are each an alkyl chain, e.g., CH 11 Represents a part.

[0145] In embodiments, R, R 1 , R 2 , or R 3 may be an alkyl group, e.g., a straight or branched chain alkyl. In embodiments, R, R 1 , R 2 , R 3At least one of the groups may be a methyl, ethyl, propyl, or butyl group.

[0146] R, R 1 , R 2 , or R 3 In embodiments where is an aromatic group, the aromatic group can be one or a combination of an aromatic hydrocarbon group and / or an aromatic heterocyclic group.

[0147] R, R 1 , R 2 , or R 3 In embodiments where is an aromatic hydrocarbon group, the aromatic hydrocarbon group may include one or a combination of phenyl and / or substituted phenyl rings. There may be one, two, three, four, or five additional substituents on the phenyl ring. The substituents are directly attached to the phenyl ring and may be one or a combination of fluorine, chlorine, bromine, iodine, hydroxyl groups, amine groups, nitro groups, alkoxy groups, carboxylic acids, amides, cyano groups, trifluoromethyl groups, esters, alkenes, alkynes, azides, azo groups, isocyanates, ketones, aldehydes, alkyl groups consisting of hydrocarbon chains or hydrocarbon rings, and alkyl groups consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen, and / or sulfur. The alkyl groups may include, for example, hydroxyl groups, amine groups, nitro groups, ether groups, carboxylic acids, amides, cyano groups, trifluoromethyl groups, esters, alkenes, alkynes, azides, azo groups, isocyanates, ketones, and aldehydes. The substituent may be another aromatic group, for example, R may comprise a phenyl substituted with an additional phenyl ring. In embodiments, the R group may be a phenyl ring substituted with a second phenyl ring, which in turn may be substituted with a third phenyl ring. In embodiments, R, R 1 , R 2 , or R 3may represent a p-fluorophenyl group, an m-fluorophenyl group, an o-fluorophenyl group, a thiophene group, a cyanophenyl moiety (e.g., a p-cyanophenyl moiety), a trifluoromethylphenyl moiety (e.g., a p-trifluoromethylphenyl moiety), an iodophenyl moiety (e.g., an o-iodophenyl moiety), a chlorophenyl moiety (e.g., an o-chlorophenyl moiety), a bromophenyl moiety (e.g., an o-bromophenyl moiety), an aminophenyl moiety (e.g., a mono-, di-, or tri-substituted aminophenyl moiety), a nitrophenyl moiety (e.g., a p-nitrophenyl moiety), or a phenol moiety.

[0148] R, R 1 , R 2 , or R 3 In embodiments where R is an aromatic group, the aromatic group can be a polycyclic aromatic hydrocarbon, such as naphthalene, anthracene, phenanthrene, tetracene, chrysene, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene, and / or benzo[c]fluorene. The R group can be attached to the triphenylene derivative by any isomer of the polycyclic aromatic hydrocarbons listed, such as 1-naphthalene, 2-naphthalene, 2-anthracene, and 9-anthracene. The polycyclic aromatic hydrocarbon group can be substituted with other moieties, such as aryl groups, alkyl groups, heteroatoms, and / or other electron-withdrawing or electron-donating groups.

[0149] R, R 1 , R 2 , or R 3In embodiments where is an aromatic heterocyclic group, the heterocyclic group can be a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring, a 8-membered ring, a 9-membered ring, a 10-membered ring, or a fused ring. In embodiments, the heterocyclic group can be furan, benzofuran, isobenzofuran, pyrrole, indole, isoindole, thiophene, benzothiophene, benzo[c]thiophene, imidazole, benzimidazole, purine, pyrazole, indazole, oxazole, benzoxazole, isoxazole, benzisoxazole, thiazole, benzothiazole, pyridine, quinoline, isoquinoline, pyrazine, quinoxaline, acridine, pyrimidine, quinozoline, pyridazine, cinnoline, phthalazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, pyridine, or thiophene.

[0150] R, R 1 , R 2 , or R 3 In embodiments where is an aliphatic group, the aliphatic group may be one or a combination of an n-alkyl chain, a branched alkyl chain, an alkyl chain containing an unsaturated portion, or an alkyl chain containing a heteroatom, such as fluorine, chlorine, bromine, iodine, oxygen, sulfur, or nitrogen. The alkyl chain may contain an unsaturated portion including an alkene or an aromatic portion. The alkyl chain may contain a functional group for further derivatization of a polycyclic aromatic hydrocarbon, such as a triphenylene derivative. For example, the functional group may be one or more of an azide, a carbonyl group, an alcohol, a halogen, an alkene, or a thioacetate.

[0151] In embodiments, R, R 1 , R 2 , or R 3 includes crown ethers.

[0152] Within the scope of this application, it is expressly intended that the various aspects, embodiments, examples, and alternatives, particularly individual features thereof, described in the preceding paragraphs, claims, and / or the following description and drawings, may be practiced independently or in any combination. That is, all embodiments and / or features of any embodiment may be combined in any manner and / or combination, except where such features are incompatible. For the avoidance of doubt, the terms "may," "and / or," "e.g.," "for example," and any similar terms used herein should be construed as open-ended, such that any feature so described is not necessarily present. Indeed, any combination of optional features, whether or not they are expressly claimed, is expressly contemplated without departing from the scope of the invention. Applicant reserves the right to modify any claim as originally filed, including the right to amend any claim as originally filed to depend on and / or incorporate any feature of any other claim not originally claimed in that form, or to file any new claim accordingly. [Brief explanation of the drawings]

[0153] To further illustrate the invention, reference is also made to the following non-limiting examples, in which reference is made to the accompanying drawings. [Figure 1] 1 is a table showing the structures of light-emitting compounds according to embodiments of the invention. [Figure 2] Synthetic routes to precursors used to produce compounds according to embodiments of the invention. [Figure 3] Absorption and emission spectra of compound 39. [Figure 4] 1 is a schematic route for conjugating an antibody to a light-emitting compound according to one embodiment of the invention. [Figure 5] 1 is a series of spectra showing the conjugation of antibodies to light-emitting compounds according to an embodiment of the invention. [Figure 6]1 is a series of images showing the conjugation of an antibody to a light-emitting compound according to an embodiment of the invention; and [Figure 7] Compound 44 according to a further embodiment of the invention. DETAILED DESCRIPTION OF THE INVENTION

[0154] Referring now to Figure 2, synthetic routes to precursors used to generate compounds according to embodiments of the invention are shown. Compounds 38-43 were synthesized from precursor 8, which in turn was synthesized from compound 3, which in turn was synthesized from precursor 2.

[0155] Precursor 2 was prepared according to the method described in N. Boden et al. J. Mater. Chem., 1995, 5, 2275.

[0156] Synthesis of compound 3 Compound 3 was synthesized using the following method. A solution of 2-naphthalenecarboxylic acid (225 mg, 1.31 mmol), palladium diacetate (0.005 mmol), and iodobenzene diacetate (0.157 mmol) in PhMe (5 mL) was heated at 70 °C for 20 min under N2. A solution of precursor 2 (100 mg; 0.131 mmol) in PhMe (2 mL) was added and heated under reflux with stirring for 48–72 h. The solution was cooled to room temperature and diluted with CHCl (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2 × 20 mL), separated, and dried under vacuum. The crude black solid was purified by flash column chromatography (silica; 40% CHCl:60% n-hexane) to give compound 3 as a yellow solid (35 mg; 32%).

[0157] The name of compound 3 is 8-(naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole.

[0158] Compound 3 had the following characterization data: 1Η NΜR(300ΜΗz,CDCl3)δH:10.22(1 H,s),8.89(1 H,s),8.49(1 H,dd,J 8.6,1.7),8.05-7.99(2 H,m),7.96-7.91(5 H,m),7.62-7.59(2 H,m),4.54(2 H,t,J 6.8),4.51(2 H,t,J 6.8),4.32-4.25(6 H,m),2.17-1.93(10 H,m),1.76-1.42(20 H,m),1.06-0.97(15 H,m)ppm. 13 C NMR(100MHz, CDCl3)δC:161.7,149.8,149.3,149.0,148.6,143.2,140.9,14 0.6,135.0,133.4,129.3,128.9,128.3,128.0,127.9,127.4,127.2,125.0,1 25.0,124.4,124.2,123.7,123.6,116.7,111.2,108.5,107.1,107.0,103.9 ,70.2,70.1,69.8,69.2,29.6,29.5,28.9,28.8,28.7,23.1,23.0,14.6,14.5 ppm.MALDI+m / z:825.5([M]+100%).IR λ-1(neat): Elemental analysis value: C,78.95;H,8.02;N,1.83%.C 54 H 67 NO6, C, 78.51; H, 8.17; N, 1.70% are necessary.

[0159] Synthesis of anterior body 8 Precursor 8 was synthesized using the following method. 8-(Naphthalen-2-yl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole (compound 3) (150 mg, 0.18 mmol, 1 equiv.) was dissolved in CHCl (10 mL) in a dried, two-necked flask fitted with a submersible seal that had been degassed for 10 min and purged with N for 10 min. The green solution was stirred under N at −10 °C for 10 min, and boron tribromide (1 M in CHCl) (0.2 mmol, 1.1 equiv.) was added via syringe through a submersible seal. The black solution was stirred under N at −10 °C for 2 h, then poured onto crushed ice and stirred until all the ice had melted. The product was then extracted with ethyl acetate (20 mL), washed with water (3 × 50 mL), and evaporated to dryness to give a brown solid. The product was then purified by flash column chromatography (20% EtOAc:n-hexane, silica) to give 8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-ol as a yellow solid (31 mg, 23%).

[0160] The name of precursor 8 is 8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-ol.

[0161] Precursor 8 had the following characterization data: 1 H NM R δ H :(300MHz,CDCl3)10.06(1H,s),8.83(1H,s),8.50(1H,dd,J 8.6,1.7),8.05-8.03(1H,m),7.79(1H,d,J 8.7),7.91-7.89(1H,m),7.84(1H,s),7.79(1H,s),7.78(1H,s),7.74(1H,s),7.58-7.56(2H,m),5.97(1H,s),4.42(2H,t,J 6.7),4.29-4.20(6H,m),2.05-1.93(8H,m),1.63-1.45(16H,m),1.05-0.98(12H,m)ppm. 13 C NMR δC :(100MHz,CDCl3)161.7,149.4,148.9,146.0,145.3,143.0,140.9,140.2,1 34.8,133.2,129.1,128.66,128.0,127.9,127.6,127.2,126.8,124.8,124.7 ,124.7,124.0,123.6,123.4,116.4,112.7,108.1,107.1,103.7,103.6,69.9 ,69.8,69.7,69.1,29.3,29.3,29.2,28.6,28.5,28.4,22.8,22.7,14.3,14.2 ppm.MALDI m / z:755.65([M] + 100%), 756.66([M+H] + 70%), 757.67([M+1+H] + twenty five%).

[0162] Example 1 - Synthesis of Compound 38 Compound 38 was synthesized by the following method. A slurry of precursor 8 (100 mg, 0.13 mmol) and K2CO3 (114 mg, 0.83 mmol) in DMF (5 mL) was heated to reflux in a CaCl2 drying tube for 0.5 h, followed by the addition of methyl 2-(2-(2-chloroethoxy)ethoxy)acetate (114 mg, 0.40 mmol) and KI (75 mg, 0.5 mmol). The resulting slurry was heated to reflux for an additional 3 h. The reaction mixture was cooled to room temperature, and the precipitate was filtered via suction filtration. The solvent was evaporated to dryness from the filtrate under vacuum, and the crude solid was purified via flash column chromatography (silica, 25% EtOAc:75% n-hexane) to give compound 38 as a yellow solid (36 mg, 30%).

[0163] The name of compound 38 is methyl 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetate.

[0164] Compound 38 had the following characterization data: 1H NMR δ H :(300MHz, CDCl3)10.16(1H,s),8.83(1H,s),8.50(1H,dd,J 8.6,1.7),8.05-8.03(2H,m),7.91-7.81(5H,m),7.58-7.56(2H,m),4.60(2H,t,J 5.5),4.42(2H,t,J 6.7),4.29-4.21(6H,m),4.20(3H,s),3.85-3.65(8H,m),2.05-1.93(8H,m),1.63-1.45(16H,m),1.05-0.98(12H,m)ppm. 13 C NMR δ C :(100MHz, CDCl3)173.9,161.7,149.4,148.9,145.9,145.3,142.0,140.8,140.4,134 .8,133.1,129.1,128.7,128.0,127.9,127.6,127.2,126.8,124.8,124.7,124.6,124 .0,123.6,123.3,116.5,112.7,108.1,107.1,103.7,103.6,71.8,71.4,71.2,70.4,6 9.8,69.8,69.7,69.0,68.5,29.4,29.3,29.2,28.6,28.5,28.4,22.8,22.7,14.3,14.2 ppm.MALDI m / z:915.7([M] + 100%),916.7([M+H] + 90%). Elemental analysis values: C, 73.41; H, 7.56; N, 1.54%.C 56 H 69 NO 10 は、C,73.42;H,7.59;N,1.53%とする.

[0165] Example 2-Synthesis of compound 39 Compound 39 was synthesized using the following method: A solution of NaOH (3 mg, 0.08 mmol) in HO (1 mL) was added to a solution of compound 38 (35 mg, 0.04 mmol) in MeOH (5 mL). The resulting solution was heated to reflux for 5 h. The reaction mixture was cooled to room temperature, and aliquots of 1 M aqueous HCl were added until no further precipitate formed. The precipitate was collected via suction filtration to give a yellow solid (24 mg, 70%).

[0166] The name of compound 39 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetic acid.

[0167] Compound 39 had the following characterization data: 1 H NM R δ H :(300MHz,CDCl3)10.16(1H,s),8.83(1H,s),8.50(1H,dd,J 8.6,1.6),8.05-8.03(2H,m),7.91-7.81(5H,m),7.58-7.56(2H,m),4.60(2H,t,J 5.5Hz),4.42(2H,t,J 6.7Hz),4.29-4.21(6H,m),3.85-3.65(8H,m),2.05-1.93(8H,m),1.63-1.45(16H,m),1.05-0.98(12H,m)ppm. 13 C NMR δ C:(100MHz,CDCl3)175.7,149.4,148.9,145.9,145.3,142.0,140.8,140.4,134.8,1 33.1,129.1,128.7,128.0,127.9,127.6,127.2,126.8,124.8,124.7,124.6,124.0, 123.6,123.3,116.5,112.7,108.1,107.1,103.7,103.6,71.8,71.4,71.2,70.4,69. 8,69.8,69.7,69.0,68.5,29.4,29.3,29.2,28.6,28.5,28.4,22.8,22.7,14.3,14.2 ppm.MALDI m / z:901.5([M] + 100%), 902.5([M+H] + 70%). Elemental analysis: C, 73.24; H, 7.52; N, 1.54%. 55 H 67 NO 10 requires C,73.23; H,7.55; N,1.55%.

[0168] Referring now to Figure 3, there is shown spectrum 30. The absorption spectrum 31 and emission spectrum 32 of compound 39 in ethyl acetate are shown.

[0169] Example 3 - Synthesis of Compound 40 Compound 40 was synthesized using the following method. A slurry of precursor 8 (100 mg, 0.13 mmol) and K2CO3 (37 mg, 0.26 mmol) in MeCN (5 mL) was heated to reflux in a CaCl2 drying tube for 0.5 h, followed by the addition of 2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (87 mg, 0.26 mmol). The resulting slurry was heated to reflux for an additional 24 h. The reaction mixture was cooled to room temperature, and the precipitate was filtered via suction filtration. The solvent was evaporated to dryness from the filtrate under vacuum, and the crude solid was purified via flash column chromatography (silica, 25% EtOAc:75% n-hexane) to give compound 38 (18 mg, 15%) as a yellow solid.

[0170] The name of compound 40 is 11-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)-8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazole.

[0171] Compound 40 had the following characterization data: 1 H NM R δ H :(300MHz,CDCl3)10.14(1H,s),8.82(1H,s),8.51(1H,dd,J 8.6,1.7),8.06-8.03(2H,m),7.91-7.80(5H,m),7.57-7.55(2H,m),4.59(2H,t,J 5.5Hz),4.41(2H,t,J 6.7Hz),4.29-4.20(6H,m),4.15-4.10(2H,m),3.87-3.82(2H,m),3.69-3.57(4H,m) ,3.30-3.21(2H,m),2.05-1.93(8H,m),1.63-1.45(16H,m),1.05-0.98(12H,m)ppm. 13 C NMR δ C :(100MHz,CDCl3)161.7,149.4,148.8,145.9,145.4,142.9,140.8,140.2,134.7,133. 2,129.1,128.7,128.0,127.9,127.6,127.1,126.9,124.8,124.7,124.6,124.0,123.6 ,123.4,116.4,112.7,108.1,107.2,103.7,103.6,72.5,70.7,70.4,70.1,69.9,69.8, 69.7,69.0,50.6,29.32,29.30,29.17,28.54,28.46,28.43,22.75,22.71,14.27,14.21 ppm.MALDI m / z:912.9([M] + 100%), 913.9 ([M+H] + 90%). Elemental analysis: C, 73.36; H, 7.55; N, 6.12%. 55 H 68 N4O8 requires C, 73.34; H, 7.51; N, 6.14%.

[0172] Example 4 - Synthesis of Compound 41 Compound 41 was synthesized using the following method. A slurry of precursor 8 (100 mg, 0.13 mmol) and K2CO3 (37 mg, 0.26 mmol) in MeCN (5 mL) was heated to reflux in a CaCl2 drying tube for 0.5 h, followed by the addition of 2-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (101 mg, 0.26 mg). The resulting slurry was heated to reflux for an additional 24 h. The reaction mixture was cooled to room temperature, and the precipitate was filtered via suction filtration. The solvent was evaporated to dryness from the filtrate under vacuum, and the crude solid was purified via flash column chromatography (silica, silica, 50% EtOAc:50% n-hexane) to give compound 38 (15 mg, 13%) as a yellow solid.

[0173] The name of compound 41 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetrakis(pentyloxy)triphenyleno[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)ethan-1-amine.

[0174] Compound 41 had the following characterization data: 1 H NM R δ H :(300MHz,CDCl3)10.13(1H,s),8.82(1H,s),8.50(1H,dd,J 8.6,1.7),8.07-8.03(2H,m),7.91-7.81(5H,m),7.57-7.57(2H,m),4.58(2H,t,J 5.5Hz),4.43(2H,t,J 6.7Hz),4.28-4.20(6H,m),4.14-4.10(2H,m),3.86-3.82(2H,m),3.69-3.57(4H,m) ,3.17-3.19(2H,m),2.04-1.92(8H,m),1.63-1.44(16H,m),1.04-0.97(12H,m)ppm. 13 C NMR δ C:(100MHz,CDCl3)161.7,149.4,148.8,145.9,145.4,142.9,140.8,140.2,134.7,13 3.2,129.1,128.7,128.0,127.9,127.6,127.1,126.9,124.8,124.7,124.6,124.0,1 23.6,123.4,116.4,112.7,108.1,107.2,103.7,103.6,72.3,70.6,70.3,70.0,69.9 ,69.8,69.7,69.0,42.5,29.4,29.3,29.2,28.5,28.5,28.4,22.75,22.7,14.3,14.2 ppm.MALDI m / z:886.5([M] + 100%), 887.6([M+H] + 70%).

[0175] Example 7 - Use of Compound 39 as an antibody-based biosensor Referring now to FIG. 4, there is shown a schematic route 3 for conjugating antibody A to a light-emitting compound LC to produce conjugated antibody A-LC, according to an embodiment of the invention.

[0176] The light-emitting compound LC used in this example was compound 39. Compound 39 was activated for conjugation in the following manner: A solution containing the following components was prepared: · 10 μL of compound 39 dissolved in DMSO at a concentration of 3.8 mg / mL (4.2 mM); · 10 μL of TSTU (N,N,N′,N′-tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate) at a concentration of 1.4 μg / mL (4.7 mM); 1 μL triethylamine to a final concentration of 0.67 μL / mL (6.6 μM).

[0177] The resulting solution was kept on a shaking incubator at room temperature for 20 minutes to produce a "biosensor solution" containing the luminescent compound and compound 39, which contains an NHS (N-hydroxysuccinimide) ester instead of a carboxylic acid functional group.

[0178] Antibody A was prepared in the following manner: 50 μL of antibody (2 mg / mL (approximately 14 μM)) was added to an Amicon® Ultra-0.5 ml filter containing a 30 kDa cutoff filter. Two dilutions / concentrations with 400 μL of additional borate buffer were used to exchange the antibody buffer for 0.1 M sodium borate buffer (pH 8.5) to generate the "antibody solution."

[0179] Antibody A was conjugated to the luminescent compound LC in the following manner: The "antibody solution" and the "biosensor solution" were directly combined and reacted at room temperature for 1 hour. Prior to characterization of the labeled conjugate by UV-vis spectroscopy, the resulting conjugated antibody A-LC was purified from unreacted luminescent compound using a standard desalting column (ZebaSpin, 7 kDa MWCO).

[0180] 5, a series of spectra are shown illustrating the conjugation of antibody A to luminescent compound LC according to this example of the invention. Spectrum 51 of antibody A alone is acquired. Spectrum 52 of luminescent compound LC (compound 39) alone is acquired. Spectrum 53 of antibody conjugated to luminescent compound A-LC is acquired.

[0181] 6, there is shown a series of images illustrating the conjugation of an antibody to a light-emitting compound according to this example of the invention. Image 61 is of light-emitting compound LC alone, image 62 is of a control sample comprising an antibody conjugated to Alexa488 (RTM) according to a comparative example of the invention, and image 63 is of an antibody conjugated to light-emitting compound A-LC according to example 7 of the invention.

[0182] Example 8 - Synthesis of Compound 44 Compound 44 was synthesized using the following method. A solution of precursor 2 (100 mg, 0.132 mmol), 3-fluorobenzoyl chloride (92 mg, 0.658 mmol), and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was heated to reflux and held at reflux for 18 h under N. The reaction was cooled to room temperature and then evaporated to dryness in vacuo and purified via flash column chromatography (silica, 60% CHCl:40% n-hexane) to afford the intermediate as a brown solid (19 mg, 18%).

[0183] The intermediate (3-fluoro-N-(2,3,6,7,10,11-hexakis(pentyloxy)triphenylen-1-yl)benzamide) (100 mg, 0.11 mmol) was dissolved in xylene (10 mL), and Wollins reagent (117.8 mg, 0.22 mmol) was added to the flask. The reaction was stirred under reflux for 24 hours and then cooled to room temperature, causing the formation of a gray precipitate. The contents of the flask were filtered through filter paper, and the filtrate was collected. The filtrate was evaporated to dryness and purified by column chromatography (silica, 40% dichloromethane:hexane) and (silica, 1% acetone:hexane) to give 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d][1,3]selenazole as a yellow solid (1.8 mg).

[0184] The name of compound 44 is 8-(3-fluorophenyl)-2,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d][1,3]selenazole.

[0185] Compound 44 had the following characterization data: 1 H NMR δ H(500MHz,CDCl3)10.40(1H,s),8.00(1H,s),7.97(1H,d,J 9.8Hz),7.95(1H,s),7.92(1H,s),7.90(1H,d,J 7.8Hz),7.87(1H,s),7.49(1H,dd,J 14.1,8.5Hz),7.24-7.21(1H,m),4.45(2H,t,J 6.8Hz),4.42(2H,t,J 6.7Hz),4.28(6H,dt,J 13.4,6.6Hz),2.06-1.94(10H,m),1.61-1.44(20H,m),1.03-0.93(15H,m)ppm.TOF LD + m / z = 860.4([M+2+H] + 30%), 859.4([M+2] + 60%), 858.4 ([M+H] + 90%), 857.4([M] + 100%), 856.4([M-2+H] + 40%), 855.4([M-2] + 60%), 854.4([M-3] + 30%), 825.5 ([TpOxPhmF + MeOH] + ),793.4([TpOxPhmF] + ).

[0186] It will be understood by those skilled in the art that any number of combinations of the features described above and / or those shown in the accompanying drawings offer distinct advantages over the prior art and, therefore, are within the scope of the invention described herein.

[0187] Some aspects and embodiments of the invention are defined by the following clauses. 1. A luminescent molecule represented by the following general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; p is an integer of 1 or 2, q and s are independently integers 1, 2, 3, or 4; Y 1, Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , and / or Y 3 can combine together to form a fused ring (e.g., a fused aromatic ring). 2. A luminescent molecule according to clause 1, represented by the following general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , Y 12 , Y 13two or more of which may combine together to form a fused ring (eg, a fused aromatic ring). 3.Y 1 ~Y 13 10. The light-emitting compound of any one of the preceding clauses, wherein one or more or all of represent or include an alkyl group, e.g., a straight chain alkyl group, a linear chain alkyl group, or a branched chain alkyl group. 4. The light-emitting compound according to clause 3, wherein the alkyl group comprises 1 to 20 carbon atoms, for example, 2 to 18 carbon atoms, 3 to 17 carbon atoms, or 4 to 16 carbon atoms. 5.Y 1 ~Y 3 , or Y 4 ~Y 13 5. The light-emitting compound of clause 3 or 4, wherein one or more or all of independently represent an alkoxy group, e.g., an OR' group, where R' is a straight or branched chain alkyl. 6.Y 1 ~Y 3 , or Y 4 ~Y 13 One or more or all of the following may be OCH3, OC2H5, OC3H7, OC4H9, OC5H 11、 OC6H 13 , OC7H 15 , OC8H 17 , OC9H 19 , or O.C. 10 H 21 6. The light-emitting compound of clause 5, comprising a linear alkoxy group selected from one or more of the following groups: 7.Y 4 , Y 7 , Y 8 , Y 11 , Y 12 7. The light-emitting compound of clause 6, wherein each represents an alkoxyl group, for example an OR' group. 8.Y 4 , Y 7 , Y 8 , Y 11 are OC5H respectively. 11 8. The light-emitting compound according to clause 7, wherein the compound represents a group. 9.Y 5 , Y 6 , Y9 , Y 10 , Y 13 9. The light-emitting compound of any one of clauses 2 to 8, wherein one or more or all of represent a hydrogen atom. 10. A light-emitting compound according to any one of the preceding clauses, represented by the following general formula: [ka] In the formula, R represents an aromatic group and / or an aliphatic group; J 1 , J 2 , J 3 , J 4 , J 5 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; J 1 and J 2 , or J 3 and J 4 may combine together to form a fused ring (e.g., a fused aromatic ring), A 1 , A 2 , A 3 , A 4 , A 5 are independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group. 11.A 1 ~A 5 11. The light-emitting compound of clause 10, wherein one or more or all of include an alkyl group. 12. The alkyl group(s) is / are CH3, C2H5, C3H7, C4H9, C5H 11、 C6H 13 , C7H 15 , C8H 17 , C9H 19 , or C10 H 21 12. The light-emitting compound of clause 10 or 11, comprising a straight chain alkyl group selected from one or more of the following alkyl groups: 13.J 1 ~J 5 13. The luminescent compound of any one of clauses 10, 11, or 12, wherein one or more of independently represent a hydrogen atom. 14.J 1 , J 2 , J 3 , J 4 , J 5 each represents a hydrogen atom, and A 1 , A 2 , A 3 , A 4 , A 5 are each alkyl chains, e.g., CH 11 14. The luminescent compound of any one of clauses 10 to 13, which represents a moiety. 15. A light-emitting compound according to any one of the preceding clauses, represented by the formula of compound 44 of the present application. 16. A light-emitting compound according to clause 1 or 2, represented by the following general formula: [ka] In the formula, R 1 and R 2 independently represent an aromatic group and / or an aliphatic group; p and q are independently an integer of 1 to 2; s is an integer from 1 to 4, Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 1 , Y 2 , or Y3 can combine together to form a fused ring (eg, a fused aromatic ring). 17. A light-emitting compound according to clause 1 or 2, represented by the following general formula: [ka] In the formula, R 1 , R 2 , R 3 independently represent an aromatic group and / or an aliphatic group; p, q, and s are each independently an integer of 1 to 2; Y 1 , Y 2 , and Y 3 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group containing a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, or a nitro group. 18. A light-emitting compound according to clause 1 or 2, represented by the following general formula: [ka] wherein R independently represents an aromatic group and / or an aliphatic group; q is independently an integer from 1 to 3; s is independently an integer from 1 to 4; t is independently an integer from 1 to 4; Y 2 , Y 3 , Y 14and J independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group containing a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group or an alkylated oxygen atom forming an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, or a nitro group; Y 2 , Y 3 , and / or Y 14 can combine together to form a fused ring (eg, a fused aromatic ring). 19. The luminescent compound according to clause 18, represented by the following general formula: [ka] wherein R independently represents an aromatic group and / or an aliphatic group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y 26 independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group (e.g., a substituted or unsubstituted group that includes a polyglycol moiety), an oxygen atom (e.g., a hydroxyl group, or an alkylated oxygen atom that forms an alkoxy group), a nitrogen atom (e.g., a primary, secondary, or tertiary amine group), a cyano group, a nitro group; Y 15 , Y 16 , Y 17 , Y 18 , Y 19 , Y 20 , Y 21 , Y 22 , Y 23 , Y 24 , Y 25 , Y26 two or more of the following may be combined together to form a fused ring (eg, a fused aromatic ring). 20.Y 15 , Y 17 , Y 18 , Y 20 , Y 21 , Y 24 , Y 25 one or more or all of each may be an OR' group, e.g., OC5H 11 20. The light-emitting compound according to clause 19, wherein the compound represents a group or an OCH3 group. 21.Y 16 , Y 19 , Y 22 , Y 23 , Y 26 21. The luminescent compound of clause 19 or 20, wherein one or more or all of each represent a hydrogen atom.

Claims

1. A light-emitting compound represented by the general formula: 【Chemical 1】 wherein X represents one of an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; Y ４ , Y ５ , Y ６ , Y ７ , Y ８ , Y ９ , Y １０ , Y １１ , Y １２ , Y １３ independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, a substituted or unsubstituted group containing a polyglycol moiety, a hydroxyl group, an alkoxy group, a primary amine group, a secondary amine group, a tertiary amine group, a cyano group, or a nitro group; Y ４ , Y ５ , Y ６ , Y ７ , Y ８ , Y ９ , Y １０ , Y １１ , Y １２ , Y １３ two or more of may combine together to form a fused ring or fused aromatic ring; Y ４ , Y ５ , Y ６ , Y ７ , Y ８ , Y ９ , Y １０ , Y １１ , Y １２ , Y １３ wherein one or more of the luminescent compounds include a spacing portion comprising a continuous linear chain of 3 to 20 covalently bonded carbon or carbon and heteroatoms, and further comprising a functional group capable of forming a covalent bond with a second species, wherein the functional group is selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl, an aldehyde or ketone, and / or an aliphatic alcohol.

2. 2. The luminescent compound of claim 1, wherein X represents an oxygen atom or a sulfur atom.

3. 3. The luminescent compound according to claim 1, wherein the functional group (FG) capable of forming a covalent bond with a second species is located at either end or at a specific end of the spacing portion.

4. 3. The luminescent compound of claim 1, wherein the spacing portion comprises a continuous chain of 3 to 20 atoms selected from carbon atoms or a combination of carbon atoms and heteroatoms.

5. 5. The luminescent compound of claim 4, wherein the spacing portion comprises or consists of a polyether chain comprising a continuous chain of 5 to 20 atoms selected from carbon and oxygen atoms.

6. The spacing moiety and the functional group (FG) capable of forming a covalent bond with a second species are selected from the group consisting of Y １ ~Y ３ or Y ４ ~Y １３ At least one of the groups is —O—(CH ２ CH ２ O) ２ CH ２ CH ２ FG portion or -O-(CH ２ CH ２ O) ２ CH ２ -O-(CH ２ CH ２ O) ２ CH ２ CH ２ -FG moiety or -(CH ２ CH ２ O) ２ CH ２ The luminescent compound of claim 5 consisting of the moiety FG.

7. Y １ ~Y ３ or Y ４ ~Y １３ 3. The light-emitting compound of claim 1, wherein one or more of: independently represents an alkoxy group.

8. 3. The luminescent compound of claim 1 or 2, comprising a single spacing moiety and a single functional group capable of forming a covalent bond with a second species.

9. Y １２ The luminescent compound of claim 8 , wherein:

10. Y ５ , Y ６ , Y ９ , Y １０ , Y １３ each represents a hydrogen atom, Y ４ , Y ７ , Y ８ , Y １１ 3. The light-emitting compound of claim 1, wherein each represents an alkoxy group.

11. A light-emitting compound represented by the general formula: 【Chemistry 2】 wherein X represents one of an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R independently represents an aromatic group and / or an aliphatic group; Y １５ , Y １６ , Y １７ , Y １８ , Y １９ , Y ２０ , Y ２１ , Y ２２ , Y ２３ , Y ２４ , Y ２５ , Y ２６ independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, a substituted or unsubstituted group including a polyglycol moiety, a hydroxyl group, an alkoxy group, a primary amine group, a secondary amine group, or a tertiary amine group, a cyano group, or a nitro group; Y １５ , Y １６ , Y １７ , Y １８ , Y １９ , Y ２０ , Y ２１ , Y ２２ , Y ２３ , Y ２４ , Y ２５ , Y ２６ two or more of which combine together to form a fused ring or fused aromatic ring; Y １５ , Y １７ , Y １８ , Y ２０ , Y ２１ , Y ２４ , Y ２５ wherein one or more of the luminescent compounds include a spacing portion comprising a continuous linear chain of 3 to 20 covalently bonded atoms selected from carbon or carbon and heteroatoms, and further comprising a functional group capable of forming a covalent bond with a second species, wherein the functional group is selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate, a carbonyl, an aldehyde, a ketone, and / or an aliphatic alcohol.

12. A light-emitting compound represented by the general formula: 【Chemistry 3】 wherein X represents one of an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom; R represents an aromatic group and / or an aliphatic group; J １ , J ２ , J ３ , J ４ , J ５ independently represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a polyether chain, a polyglycol group, a substituted or unsubstituted group containing a polyglycol moiety, a hydroxyl group, an alkoxy group, a primary amine group, a secondary amine group, or a tertiary amine group, a cyano group, or a nitro group; J １ and J ２ , or J ３ and J ４ may combine together to form a fused ring or a fused aromatic ring; A １ , A ２ , A ３ , A ４ , A ５ one or more of independently represent a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group, and further comprise a functional group capable of forming a covalent bond with a second species; A １ , A ２ , A ３ , A ４ , A ５ the remainder of which independently represent a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a polyether group.

13. 13. The light-emitting compound of claim 12, wherein the functional group is selected from a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, a thiol moiety, an isothiocyanate, a carbonyl, an aldehyde, a ketone, and / or an aliphatic alcohol.

14. A １ , A ２ , A ３ , A ４ , A ５ 14. The light-emitting compound of claim 12 or 13, wherein four out of five of independently represent an alkyl group.

15. A １ , A ２ , A ３ , A ４ , A ５ 14. The luminescent compound of claim 12 or 13, wherein one of five of the above comprises or consists of a spacing moiety and a functional group capable of forming a covalent bond with a second species.

16. The luminescent compound of claim 15 , wherein the spacing moiety is a polyether moiety.

17. 17. The luminescent compound according to claim 15 or 16, wherein the functional group (FG) is provided at the end of the spacing portion.

18. The spacing portion and functional group have the following structure: -O-(CH ２ CH ２ O) ２ CH ２ CH ２ FG or -O-(CH ２ CH ２ O) ２ CH ２ 18. The luminescent compound of claim 17, consisting of FG.

19. X represents an oxygen atom; １ , J ２ , J ３ , J ４ , J ５ 14. The luminescent compound of claim 12 or 13, wherein independently represent a hydrogen atom.

20. 13. The light-emitting compound according to claim 1 or 12, wherein R represents an aromatic group.

21. 21. The light-emitting compound of claim 20, wherein R represents one of a phenyl group, a substituted phenyl group, a polycyclic aromatic hydrocarbon, and a naphthalene group.

22. A light-emitting compound according to any one of compounds 38 to 43 shown below. 【Chemistry 4-1】 【Chemistry 4-2】 。

23. 13. The luminescent compound of claim 1 or 12, covalently bonded to a second species.

24. 24. The luminescent compound of claim 23, wherein the second species is selected from a small molecule, a solid support, or a biomolecule.

25. 25. The luminescent compound of claim 24, wherein the biomolecule is one of an antibody, a protein, and a polynucleotide.

26. 13. A kit of components suitable for use in covalently bonding any of the luminescent compounds of claim 1 or 12 to a second species, said kit components comprising one or more luminescent compound(s) of the invention and a solvent suitable for dissolving or suspending said luminescent compound(s).

27. 27. A kit component according to claim 26, wherein the second species is a biomolecule.

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