Luminescent compounds

Abstract

A light-emitting compound represented by the following general formula: 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 an integer of 1, 2, 3 or 4; Y 1 、Y 2 and Y 3 independently comprises, consists of or 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, an oxygen atom, a nitrogen atom, a cyano group or a nitro group; Y 1 、Y 2 and / or Y 3 Two or more of can be combined together to form a fused ring; wherein Y 1 、Y 2 and / or Y 3 One or more of the moieties comprises a spacer comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 group and / or an aliphatic alcohol.

Description

[0001] The present invention generally relates to light-emitting compounds. More particularly, although not exclusively, the present invention relates to light-emitting compounds capable of forming a covalent bond with a second substance, such as a biomolecule, for use as chemical sensors or biosensors.

[0002] Fluorescent dyes are often used as labels, such as cell and tissue markers. Such dyes can be used in a wide range of biological applications, such as immunofluorescence assays, flow cytometry, fluorescence microscopy, protein blotting, 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 more than twenty different fluorescent dyes that exhibit emission spectra spanning the near UV, visible, and near IR spectral ranges.

[0005] It is known to conjugate fluorescent dyes to target biomolecules or substances by forming a covalent bond between the fluorescent dye and the biomolecule. For example, it is known to conjugate fluorescent dyes to antibodies. This can be used to track the conjugated antibody to visualize its interaction with a specific antigen. Typically, fluorescent dyes form a covalent bond with the biomolecule via functional groups located on the fluorescent dye, such as thiol-reactive or amine-reactive functional groups.

[0006] Fluorescent dyes typically 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 multiplexed assay systems. Multiplexed assays combine the assays for many target analytes in a single reaction volume. This reduces workflow and sample volume issues. It is also known to use combinations of different fluorescent dyes to detect different analytes. However, different dyes typically require different excitation wavelengths, which increases system complexity.

[0008] It would be advantageous to provide a range of luminescent compounds for labelling molecules, for example biomolecules such as antibodies, which can be excited at the same or similar wavelengths but emit at different wavelengths.

[0009] Therefore, a first aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0010]

[0011] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0012] R represents an aromatic group and / or an aliphatic group;

[0013] p is an integer of 1 or 2;

[0014] q and s are independently an integer of 1, 2, 3 or 4;

[0015] Y 1 、Y 2 and Y 3 independently comprises, consists of or represents a hydrogen atom, a deuterium atom, a halogen atom (e.g., 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 comprising 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;

[0016] Y 1 、Y 2 and / or Y 3 Two or more of can be combined together to form a fused ring (e.g., a fused aromatic ring);

[0017] where Y 1 、Y 2 and / or Y 3 One or more of the moieties comprises a spacer comprising a continuous chain of three to twenty atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 group (e.g., an aldehyde or a ketone) and / or an aliphatic alcohol.

[0018] In an embodiment, the second substance 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 an embodiment, the second substance is a therapeutic substance or a pharmaceutically active molecule, such as a drug molecule.

[0019] Advantageously, the luminescent compounds of the present invention are capable of being covalently bonded to a second substance that can specifically bind to a target molecule and can therefore be used as chemical sensors or biosensors.

[0020] We define a biosensor as a sensor comprising or consisting of a luminescent compound that can be used to detect a chemical or biological substance or to determine the concentration of a chemical or biological substance.

[0021] Additionally or alternatively, the second substance may be a solid support, e.g., for solid phase synthesis. Additionally or alternatively, the second substance may be a nanoparticle, e.g., a nanoparticle comprising or formed from a metal or metal alloy, carbon, clay, polymer, and / or ceramic material.

[0022] In an embodiment, X represents an oxygen atom. In an embodiment, X represents a sulfur atom.

[0023] Y 1 、Y 2 and / or Y 3 The one or more spacers in the alkylene group may comprise a continuous chain of 3 to 20 atoms, for example 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, for example 9 atoms. The atoms may be selected from carbon atoms or a combination of carbon atoms and heteroatoms such as oxygen atoms and / or nitrogen atoms.

[0024] When referring to the continuous chain of the spacer by a continuous chain of 3 to 20 atoms, we mean the carbon atoms or a combination of carbon atoms and heteroatoms that are covalently bonded in an uninterrupted straight chain of 3 to 20 atoms to form the backbone. The carbon atoms and / or heteroatoms (which form the backbone of the spacer) may have other atoms attached or bonded thereto, such as hydrogen atoms, branched alkyl or aryl groups, which are not included as part of the definition of a continuous chain of 3 to 20 atoms.

[0025] It should be understood that the spacer and the functional group are different moieties and that their definitions do not overlap. That is, the functional group is distinct from the continuous chain of 3 to 20 atoms of the spacer.

[0026] In embodiments, the continuous chain of spacers may comprise a continuous chain of one of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0027] Y 1 、Y 2 and / or Y 3 One or more of the spacers in may comprise or consist of a polyether chain covalently bonded to a functional group capable of forming a covalent bond with the second substance. 1 、Y 2 and / or Y 3One or more of the spacers in may comprise or consist of a polyether chain comprising a continuous chain of five to twenty atoms, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 atoms selected from carbon atoms and oxygen atoms. 1 、Y 2 and / or Y 3 The continuous chain of one or more spacers in may comprise or consist of a polyether chain having a continuous chain of nine atoms selected from carbon and oxygen.

[0028] In an embodiment, a functional group (FG) capable of forming a covalent bond with the second substance may be located at a terminal end of the spacer.

[0029] In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2CH2- portion. In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2- portion. The functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer such that Y 1 、Y 2 and / or Y 3 One or more of them consists of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0030] In an embodiment, the luminescent compound is a triphenylene derivative, that is, the luminescent compound comprises a triphenylene core. In an embodiment, the luminescent compound comprises a core comprising a polycyclic aromatic hydrocarbon, for example, comprising five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, or twenty or more fused six-membered rings. For example, the luminescent compound may comprise a core comprising a polycyclic aromatic hydrocarbon comprising six fused six-membered rings.

[0031] In an embodiment, the luminescent compound is represented by the following general formula:

[0032]

[0033] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0034] R represents an aromatic group and / or an aliphatic group;

[0035] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y11 、Y 12 、Y 13 independently comprises, consists of or 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 comprising 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;

[0036] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 Two or more of can be combined together to form a fused ring (e.g., a fused aromatic ring);

[0037] where 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 moieties comprises a spacer comprising a continuous chain of three to twenty atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 group (e.g., an aldehyde or a ketone) and / or an aliphatic alcohol.

[0038] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 The one or more spacers in the alkylene group may comprise a continuous chain of 3 to 20 atoms, for example, 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, for example, 9 atoms. The atoms may be carbon atoms or a combination of carbon atoms and heteroatoms such as oxygen atoms and / or nitrogen atoms.

[0039] In embodiments, the continuous chain of spacers may comprise a continuous chain of one of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0040] 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 spacers in may comprise or consist of a polyether chain covalently bonded to a functional group capable of forming a covalent bond with the second substance. 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 One or more of the spacers in may comprise or consist of a polyether chain comprising a continuous chain of five to twenty atoms, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 atoms selected from carbon atoms and oxygen 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 spacers in may comprise or consist of a polyether chain having a continuous chain of nine atoms selected from carbon and oxygen.

[0041] In an embodiment, the functional group (FG) capable of forming a covalent bond with the second substance may be located at the spacer or at a terminal end of the spacer.

[0042] In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2CH2- portion. In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2- portion. The functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer such that Y 4 、Y 5 、Y 6 、Y7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 One or more of them consists of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0043] In the luminescent compound of the present 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 the Y comprises a spacer 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 may not contain such spacers and / or functional groups. In an embodiment, Y 4 、Y 5 、Y 5 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 A single one of Y may contain a spacer and a functional group, while the rest do not contain a spacer and a functional group. 12 Contains a spacer and a functional group, and Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 13 It does not contain spacers or functional groups.

[0044] In Y 1 To Y 3 or Y 4 To Y 13When one or more or all except one of the above do not contain a spacer and a functional group, Y 1 To Y 13 May represent or include an alkyl group. The one or more alkyl groups may be straight or linear chains, or may include branches, and / or may be further functionalized. Additionally or alternatively, Y 1 To Y 3 or Y 4 To Y 13 may independently represent or include an aryl group. The one or more aryl groups may be unsubstituted or may be further functionalized. In an embodiment, Y 4 To Y 13 The polyether chain or polyglycol chain may independently represent or comprise a polyether chain or polyglycol group, such as a polyethylene glycol moiety. The polyether chain or polyglycol chain may comprise a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0045] In an embodiment, Y 1 To Y 3 or Y 4 To Y 13 One or more of may independently represent or include an alkoxy group, for example an OR' group, wherein R' is a linear or branched alkyl chain. The alkyl chain may contain 1 to 20 carbon atoms, for example 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.

[0046] In an embodiment, Y 1 To Y 3 One or more of, for example all but one, or Y 4 To Y 13 All except one of the above may comprise or consist of a linear alkoxy group selected, for example, from OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 One or more or a combination of groups.

[0047] In an embodiment, Y 5 、Y 6 、Y 9 、Y 10 、Y 13 Each represents a hydrogen atom.

[0048] In an embodiment, Y 4 、Y 7 、Y 8 、Y 11 Each represents an OR' group. The OR' group can be selected from OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 For example, Y 4 、Y 7 、Y 8 、Y 11 Can each represent OC5H 11 group.

[0049] In an embodiment, Y 12 represents a spacer and a functional group capable of forming a covalent bond with the second substance. For example, Y 12 It may represent an O-(CH2CH2O)2CH2CH2FG moiety or an -O-(CH2CH2O)2CH2FG moiety, wherein FG is a functional group capable of forming a covalent bond with a second substance.

[0050] For example, in embodiments, X represents an oxygen atom, and / or Y 5 、Y 6 、Y 9 、Y 10 、Y 13 Each represents a hydrogen atom, Y 4 、Y 7 、Y 8 、Y 11 Each represents an OR' group (e.g. OC5H 11 group), and Y 12 Represents the -O-(CH2CH2O)2CH2CH2FG portion.

[0051] In an embodiment, Y 8 represents an oxygen atom, and Y 9 represents nitrogen atom, Y 8 and Y 9The linkage forms an oxazole moiety comprising an R group selected from aromatic and / or aliphatic groups.

[0052] In an embodiment, the luminescent compound is represented by the following general formula:

[0053]

[0054] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0055] R 1 and R 2 independently represent an aromatic group and / or an aliphatic group;

[0056] p and q are independently integers from 1 to 2;

[0057] s is an integer from 1 to 4;

[0058] Y 1 、Y 2 and Y 3 independently comprises, consists of or 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 comprising 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;

[0059] Y 1 、Y 2 or Y 3 Two or more of can be combined together to form a fused ring (e.g., a fused aromatic ring);

[0060] where Y 1 、Y 2 、Y 3 One or more of the moieties comprises a spacer comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 carbonyl (e.g., an aldehyde or a ketone) and / or an aliphatic alcohol.

[0061] In embodiments comprising more than one X atom, preferably the X atoms are heteroatoms of the same type, ie, one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a selenium atom.

[0062] In an embodiment, Y 6 represents an oxygen atom, and Y 7 represents nitrogen atom, Y 6 and Y7 The bond forms an oxazole moiety comprising an R group selected from an aromatic group and / or an aliphatic group. Additionally or alternatively, Y 11 represents an oxygen atom, and Y 10 represents nitrogen atom, Y 11 and Y 10 The linkage forms an oxazole moiety comprising an R group selected from an aromatic group and / or an aliphatic group. In an embodiment, the emissive compound comprises one, two or three oxazole moieties.

[0063] In an embodiment, the luminescent compound is represented by the following general formula:

[0064]

[0065] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0066] R 1 、R 2 、R 3 independently represent an aromatic group and / or an aliphatic group;

[0067] p, q and s are each independently an integer from 1 to 2;

[0068] Y 1 、Y 2 and Y 3 independently comprises, consists of or 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 comprising 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;

[0069] where Y 1 、Y 2 、Y 3 One or more of the moieties comprises a spacer comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 carbonyl (e.g., an aldehyde or a ketone) and / or an aliphatic alcohol.

[0070] Preferably, R 1 、R 2 、R 3 represents the same type of group, such as R 1 、R 2 、R 3may each represent a naphthyl group.

[0071] In an embodiment, Y 5 and Y 6 It represents carbon atoms grouped together to form a fused ring, such as a fused aromatic ring fused to the nucleus of the emissive compound.

[0072] In an embodiment, the luminescent compound may be represented by the following general formula:

[0073]

[0074] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0075] R independently represents an aromatic group and / or an aliphatic group;

[0076] q is independently an integer from 1 to 3;

[0077] s is independently an integer from 1 to 4;

[0078] t is independently an integer from 1 to 4;

[0079] Y 2 、Y 3 and Y 14 and J independently comprises, consists of, or 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 comprising 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;

[0080] Y 2 、Y 3 and / or Y 14 Two or more of can be combined together to form a fused ring (e.g., a fused aromatic ring);

[0081] where Y 2 、Y 3 、Y 14 and / or one or more of J comprises a spacer comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 carbonyl (e.g., an aldehyde or ketone) and / or an aliphatic alcohol.

[0082] Y 2 、Y 3 、Y 14The spacer of one or more of J and / or J comprises a continuous chain of 3 to 20 atoms, for example, 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, for example, 9 atoms. The atoms may be carbon atoms or a combination of carbon atoms and heteroatoms such as oxygen atoms and / or nitrogen atoms.

[0083] In embodiments, the continuous chain of spacers may comprise a continuous chain of one of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0084] Y 2 、Y 3 、Y 14 One or more of the spacers in and / or J may comprise or consist of a polyether chain covalently bonded to a functional group capable of forming a covalent bond with a second substance. 2 、Y 3 、Y 14 The spacer of one or more of and / or J may comprise or consist of a polyether chain comprising a continuous chain of five to twenty atoms, e.g., 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 atoms selected from carbon atoms and oxygen atoms. 2 、Y 3 、Y 14 The continuous chain of spacers of one or more of and / or J may comprise or consist of a polyether chain having a continuous chain of nine atoms selected from carbon and oxygen.

[0085] In an embodiment, the functional group (FG) capable of forming a covalent bond with the second substance may be located at the spacer or at a terminal end of the spacer.

[0086] In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2CH2- portion. In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2- portion. The functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer such that Y 2 、Y 3 、Y 14 and / or one or more of J consists of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0087] In embodiments, the one or more luminescent compounds may be represented by the following general formula:

[0088]

[0089] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0090] R independently represents an aromatic group and / or an aliphatic group;

[0091] 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 comprises, consists of or 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 comprising 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;

[0092] 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 are combined together to form a fused ring (e.g., a fused aromatic ring);

[0093] where 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 moieties comprises a spacer comprising a continuous chain of 3 to 20 atoms and further comprising a functional group capable of forming a covalent bond with a second substance, 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 carbonyl (e.g., an aldehyde or a ketone) and / or an aliphatic alcohol.

[0094] Y 15 、Y 16 、Y 17 、Y 18 、Y 19 、Y 20 、Y 21 、Y 22 、Y 23 、Y 24 、Y 25 、Y 26 The one or more spacers in the alkylene group may comprise a continuous chain of 3 to 20 atoms, for example, 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, for example, 9 atoms. The atoms may be carbon atoms or a combination of carbon atoms and heteroatoms such as oxygen atoms and / or nitrogen atoms.

[0095] In embodiments, the continuous chain of spacers may comprise a continuous chain of one of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0096] 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 spacers in may comprise or consist of a polyether chain covalently bonded to a functional group capable of forming a covalent bond with the second substance. 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 spacers in may comprise or consist of a polyether chain comprising a continuous chain of five to twenty atoms, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 atoms selected from carbon atoms and oxygen 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 spacers in may comprise or consist of a polyether chain having a continuous chain of nine atoms selected from carbon and oxygen.

[0097] In an embodiment, a functional group (FG) capable of forming a covalent bond with the second substance may be located at a terminal end of the spacer.

[0098] In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2CH2- portion. In an embodiment, the spacer may consist of a -O-(CH2CH2O)2CH2- portion. The functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer such that 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 them consists of -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

[0099] In an embodiment, Y 21 represents an oxygen atom, and Y 22 represents nitrogen atom, Y 21 and Y 22 The linkage forms an oxazole moiety comprising an R group selected from aromatic and / or aliphatic groups.

[0100] where 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 except one do not contain a spacer and a functional group, Y 15 、Y 16 、Y17 、Y 18 、Y 19 、Y 20 、Y 21 、Y 22 、Y 23 、Y 24 、Y 25 、Y 26 Can independently represent or include alkyl groups. Said one or more alkyl groups can be straight or linear chains, or can include branches, and / or can 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 one or more aryl groups may be unsubstituted or may be further functionalized. 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 The polyether chain or polyglycol chain may independently represent or comprise a polyether chain or polyglycol group, such as a polyethylene glycol moiety. The polyether chain or polyglycol chain may comprise a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0101] 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 26One or more of may independently represent or include an alkoxy group, for example an OR' group, wherein R' is a linear or branched alkyl chain. The alkyl chain may contain 1 to 20 carbon atoms, for example 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.

[0102] 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, for example all except one, may comprise a linear alkoxy group selected from, for example, OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 One or more groups.

[0103] In an embodiment, Y 16 、Y 19 、Y 22 、Y 23 、Y 26 Each represents a hydrogen atom.

[0104] 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 Can each represent OC5H 11 Group. For example, Y 17 、Y 18 may each represent an OCH3 group.

[0105] In an embodiment, Y 15 、Y17 、Y 18 、Y 20 、Y 21 、Y 24 、Y 25 One or more (e.g. only Y 17 ) represents a spacer and a functional group. For example, Y 17 It may represent -O-(CH2CH2O)2CH2CH2FG, wherein FG is a functional group capable of forming a covalent bond with a second substance.

[0106] For example, in an embodiment, X represents an oxygen atom, Y 16 、Y 19 、Y 22 、Y 23 、Y 26 Each represents a hydrogen atom, Y 15 、Y 20 、Y 21 、Y 24 、Y 25 Each represents OC5H 11 Group, Y 18 represents an OCH3 group, and Y 17 Represents the -O-(CH2CH2O)2CH2CH2FG portion.

[0107] Another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0108]

[0109] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0110] R represents an aromatic group and / or an aliphatic group;

[0111] J 1 、J 2 、J 3 、J 4 、J 5 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 comprising 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;

[0112] Among them J 1 、J 2 can be combined to form fused rings (e.g., fused aromatic rings);

[0113] A1 、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; and

[0114] Among them A 1 、A 2 、A 3 、A 4 、A 5 One or more of the compounds comprises a functional group capable of forming a covalent bond with a second substance.

[0115] In embodiments, the functional group may be selected from one or more of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate carbonyl (eg, an aldehyde or a ketone), and / or an aliphatic alcohol.

[0116] In the embodiment, J 1 、J 2 、J 3 、J 4 、J 5 In an embodiment, J 1 、J 2 、J 3 、J 4 、J 5 represents deuterium atoms independently.

[0117] In an embodiment, R represents an aliphatic group or moiety. In an embodiment, R represents an aromatic group or moiety.

[0118] In all embodiments, the term "fused ring" is intended to define groups bonded together to form a ring (eg, an aromatic ring and / or a heterocyclic ring) that forms part of the core of the emissive compound, ie, expands the triphenylene core.

[0119] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0120]

[0121] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0122] R represents an aromatic group and / or an aliphatic group;

[0123] J 5 、J 6 、J 7 、J 8 、J 9 、J 10 、J11 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 comprising 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;

[0124] J 6 and J 7 or J 8 and J 9 can be combined to form fused rings (e.g., fused aromatic rings);

[0125] 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; and

[0126] Among them A 6 、A 7 、A 8 、A 9 、A 10 、A 11 One or more of the compounds comprises a functional group capable of forming a covalent bond with a second substance.

[0127] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0128]

[0129] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0130] R 1 and R 2 independently represent an aromatic group and / or an aliphatic group;

[0131] J 12 、J 13 、J 14 、J 15 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 comprising 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;

[0132] Among them J 12 and J 13 can be combined to form fused rings (e.g., fused aromatic rings);

[0133] 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; and

[0134] Among them A 12 、A 13 、A 14 、A 15 One or more of the compounds comprises a functional group capable of forming a covalent bond with a second substance.

[0135] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0136]

[0137] wherein X represents one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom or a selenium atom;

[0138] R 1 、R 2 、R 3 independently represent an aromatic group and / or an aliphatic group;

[0139] J 16 、J 17 、J 18 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 comprising 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;

[0140] 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; and

[0141] Among them A 16 、A 17 、A 18 One or more of the compounds comprises a functional group capable of forming a covalent bond with a second substance.

[0142] The functional group capable of forming a covalent bond with the second substance may be selected from one of carboxylic acid, ester, azide, amine, maleimide, thiol, isothiocyanate carbonyl (eg, aldehyde or ketone) and / or aliphatic alcohol.

[0143] In an embodiment, A comprises a functional group capable of forming a covalent bond with a second substance. 1 、A 2 、A 3 、A 4 、A 5 One or more of, or A 6 、A 7 、A 8 、A 9 、A 10 、A 11 One or more of, or A 12 、A 13 、A 14 、A 15 One or more of, or A 16 、A 17 、A 18 One or more of the moieties may further comprise a spacer. The spacer may comprise a continuous chain of 3 to 20 atoms, for example, 4 to 18 atoms, or 5 to 16 atoms, or 6 to 14 atoms, or 7 to 12 atoms, or 8 to 10 atoms, for example, 9 atoms. The atoms may be selected from carbon atoms or a combination of carbon atoms and heteroatoms such as oxygen atoms and / or nitrogen atoms.

[0144] In embodiments, the continuous chain of spacers may comprise a continuous chain of one of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 atoms.

[0145] A 1 、A 2 、A 3 、A 4 、A 5 One or more of, or A 6 、A 7 、A 8 、A 9 、A 10 、A 11 One or more of, or A 12 、A 13 、A 14 、A 15 One or more of, or A 16 、A 17 、A 18One or more of the spacers may comprise or consist of a polyether chain covalently bonded to a functional group capable of forming a covalent bond with a second substance. 1 To A 18 One or more of the spacers in may comprise or consist of a polyether chain comprising a continuous chain of five to twenty atoms, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 atoms selected from carbon atoms and oxygen atoms. 1 To A 18 The continuous chain of one or more spacers in may comprise or consist of a polyether chain having a continuous chain of nine atoms selected from carbon and oxygen.

[0146] In an embodiment, the functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer. 1 To A 18 One or more of the alkyl groups may be terminated with one of a carboxylic acid, an ester, an azide, an amine, a maleimide, a thiol, an isothiocyanate carbonyl (eg, an aldehyde or ketone), and / or an aliphatic alcohol.

[0147] In an embodiment, the spacer may consist of a -(CH2CH2O)2CH2CH2- moiety. In an embodiment, the spacer may consist of a -(CH2CH2O)2CH2- moiety. The functional group (FG) capable of forming a covalent bond with the second substance may be located at the end of the spacer such that A 1 、A 2 、A 3 、A 4 、A 5 One or more of, or A 6 、A 7 、A 8 、A 9 、A 10 、A 11 One or more of, or A 12 、A 13 、A 14 、A 15 One or more of, or A 16 、A 17 、A 18 One or more of them consists of -(CH2CH2O)2CH2CH2FG or -(CH2CH2O)2CH2FG.

[0148] In A 1 、A 2 、A 3 、A 4 、A 5One or more or all but one of A 6 、A 7 、A 8 、A 9 、A 10 、A 11 One or more of, or A 12 、A 13 、A 14 、A 15 One or more of, or A 16 、A 17 、A 18 In the case where one or more of the two substituents do not contain a spacer and a functional group capable of forming a covalent bond with the second substance, A 1 To A 18 One or more of A may contain an alkyl group. The one or more alkyl groups may be straight or linear chains, or may contain branches, and / or may be further functionalized. Additionally or alternatively, A 1 To A 18 Aryl groups may be included independently. The one or more aryl groups may be unsubstituted or may be further functionalized.

[0149] In the 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, for example all except one, may comprise or consist of a linear alkyl group, for example independently selected from CH3, C2H5, C3H7, C4H9, C5H 11 、C6H 13 、C7H 15 、C8H 17 、C9H 19 or C 10 H 21 One or more of the alkyl groups.

[0150] In the embodiment, A 1 To A 18The polyether chain or polyglycol chain may independently comprise a polyether chain or polyglycol group, such as a polyethylene glycol moiety. The polyether chain or polyglycol chain may comprise a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0151] The luminescent compound of the present invention may comprise a single functional group capable of forming a covalent bond with a second substance, i.e., a single functional group selected from carboxylic acid, ester, azide, amine, maleimide, thiol, isothiocyanate carbonyl (e.g., aldehyde or ketone) and / or aliphatic alcohol. In an alternative embodiment, the luminescent compound may comprise two or more functional groups capable of forming a covalent bond with a second substance. For example, A 1 To A 18 In the embodiment comprising more than one functional group capable of forming a covalent bond with a second substance, functional groups of the same type or different types (i.e., a first type and a second type different from the first type) can be selected.

[0152] In an embodiment, R, R 1 、R 2 and / or R 3 It can be an alkyl group, such as a straight or branched alkyl chain. In an embodiment, R, R 1 、R 2 、R 3 At least one of the groups may be a methyl, ethyl, propyl or butyl group.

[0153] In R, R 1 、R 2 and / or R 3 In the embodiment where the aromatic group is present, the aromatic group may be one or a combination of an aromatic hydrocarbon group and / or an aromatic heterocyclic group.

[0154] In R, R 1 、R 2 and / or R 3In the embodiment of the aromatic hydrocarbon group, the aromatic hydrocarbon group can include one or combination of phenyl ring and / or substituted phenyl ring.On the phenyl ring, one, two, three, four or five other substituents can be present.The substituent is directly bonded to the phenyl ring and can be one or combination of the following groups: fluorine, chlorine, bromine, iodine, hydroxyl group, amine group, nitro group, alkoxy group, carboxylic acid, amide, cyano group, trifluoromethyl, ester, alkene, alkynes, azide, azo, isocyanate, ketone, aldehyde, the alkyl group consisting of hydrocarbon chain or hydrocarbon ring, the alkyl group consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen and / or sulphur.The alkyl group can include for example hydroxyl group, amine group, nitro group, ether group, carboxylic acid, amide, cyano group, trifluoromethyl, ester, alkene, alkynes, azide, azo, isocyanate, ketone, aldehyde.The substituent can be another aromatic group, for example, and R can include the phenyl substituted by another phenyl ring. In an embodiment, the R group can be a benzene ring substituted with a second benzene ring, which in turn is substituted with a third benzene ring. 1 、R 2 or R 3 It can represent a p-fluorophenyl group, an m-fluorophenyl group, an o-fluorophenyl group, a thienyl 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-substituted, di-substituted, or tri-substituted aminophenyl moiety), a nitrophenyl moiety (e.g., a p-nitrophenyl moiety), or a phenol moiety.

[0155] In R, R 1 、R 2 and / or R 3 In embodiments where R is an aromatic group, the aromatic group may be a polycyclic aromatic hydrocarbon, such as naphthalene, anthracene, phenanthrene, tetracene, phenanthracene, 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 bonded to the triphenylene derivative through any isomer of the polycyclic aromatic hydrocarbon, such as 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.

[0156] In an embodiment, R, R 1 、R 2 and / or R 3 It's naphthalene.

[0157] In R, R1 、R 2 and / or R 3 In embodiments where the heterocyclic group is an aromatic heterocyclic group, the heterocyclic group may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a nine-membered ring, a ten-membered ring, or a fused ring. In embodiments, the heterocyclic group may 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, quinazoline, pyridazine, cinnoline, phthalazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, pyridine, or thiophene.

[0158] In R, R 1 、R 2 and / or R 3 In embodiments where the aliphatic group is an aliphatic group, the aliphatic group can be one or a combination of the following groups: a normal alkyl chain, a branched alkyl chain, an alkyl chain containing an unsaturated moiety, an alkyl chain containing heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, sulfur, or nitrogen. The alkyl chain can contain an unsaturated moiety (including an olefin) or an aromatic moiety. The alkyl chain can contain a functional group for further derivatization of a polycyclic aromatic hydrocarbon (e.g., triphenylene) derivative. For example, the functional group can be one or more of an azide, a carbonyl group, an alcohol, a halogen, an olefin, or a thioacetate.

[0159] In an embodiment, R, R 1 、R 2 and / or R 3 Contains crown ether.

[0160] Yet another aspect of the present invention provides any one of the light-emitting compounds according to the present invention covalently bonded to a second substance.

[0161] In embodiments, the second substance can be a small molecule and / or a biomolecule. For example, the second substance can be an amino acid, a peptide, a protein, a nucleic acid, or a polynucleotide. The second substance need not be a molecule. For example, the second substance can be an antibody. In embodiments, the second substance is a therapeutic substance or a pharmaceutically active molecule, such as a drug molecule.

[0162] Advantageously, the luminescent molecule according to the present invention is suitable for covalent bonding to a second substance, such as a biomolecule or a small molecule or a drug molecule.Thus, the luminescent molecule can be used as a biosensor.

[0163] The biomolecule can be an antibody, such as a monoclonal antibody or a polyclonal antibody. The biomolecule can be an anti-biotin protein, such as streptavidin. The biomolecule can be biotin.

[0164] In an embodiment, the second substance can be a molecule for identifying a substance in a biological system. For example, a biomolecule can be capable of binding to a protein or receptor on the cell surface.

[0165] Yet another aspect of the present invention provides a biomolecule, such as an antibody, covalently bonded to any one of the light-emitting compounds of the present invention.

[0166] Yet another aspect of the present invention provides a multi-component kit suitable for covalently bonding any one of the light-emitting compounds of the present invention to a second substance, such as a biomolecule, the multi-component kit comprising one or more light-emitting compounds of the present invention and a solvent suitable for dissolving or suspending the one or more light-emitting compounds.

[0167] The solvent may include water, for example, an aqueous medium and / or a buffered 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 including an aqueous medium and a second solvent including an organic solvent such as THF or DMSO or a combination thereof.

[0168] In some embodiments, the kit of parts may further comprise a second substance.

[0169] The kit of parts may also include a set of instructions explaining how to covalently bond the light-emissive compound of the present invention to a second substance.

[0170] The kit of parts may further comprise a catalyst and / or a coupling agent for covalently bonding the light-emissive compound of the invention to a second substance.

[0171] The multi-part kit may further comprise a measuring device, such as a pipette or a pipette tip.The multi-part kit may further comprise a container suitable for performing the covalent bonding reaction of the luminescent compound with the second substance.

[0172] Yet another aspect of the present invention provides a method for conjugating the light-emitting compound of the present invention to a second substance, the method comprising providing a light-emitting molecule, providing a second substance, and forming a covalent bond between the light-emitting compound and the second substance.

[0173] The method may comprise adding a second substance, such as a solution or suspension of the second substance, to the solution of the luminescent molecule. The method may comprise adding a luminescent molecule, such as a solution of the luminescent molecule, to the solution or suspension of the second substance.

[0174] Advantageously, the luminescent compounds of the present invention can be used, for example, to locate and / or track the second substance in vivo when conjugated (ie, covalently bonded) to the second substance. The conjugated luminescent molecule and the second substance can also be used to locate and / or track the target substance of the second substance.

[0175] Yet another aspect of the present invention provides use of one or more luminescent compounds according to the present invention or conjugates thereof in a composition for cell or tissue imaging.

[0176] By conjugate of a light-emitting molecule we mean the light-emitting compound when covalently bonded to a second substance.

[0177] Yet another aspect of the present invention provides use of a luminescent compound or a conjugate thereof in immunofluorescence technology.

[0178] Yet another aspect of the present invention provides use of a luminescent compound or a conjugate thereof in flow cytometry.

[0179] Luminescent substances and their conjugates can be used, for example, to quantify and / or detect the presence of a second substance or a target in an assay. Luminescent substances and their conjugates can be used to quantify and / or detect the presence of biomolecules, such as DNA, RNA, proteins, hormones, antibodies, or cells. In this way, luminescent compounds and their conjugates can be used as biosensors.

[0180] The luminescent compound according to the present invention can be used to form a covalent bond with a second substance present in vivo or in vitro. For example, the covalent bond between the luminescent compound and the second substance can be formed in tissue culture or cell culture such as plant, animal or microbial cell culture.

[0181] The conjugates of the luminescent compound of the present invention and a second substance can be used in vivo, for example, to track or locate the second substance in vivo, or to track or locate a target of the second substance in vivo. The conjugates of the luminescent compound can be used to produce images of organs, for example, in which the conjugate has accumulated. Images produced, for example, using fluorescence imaging techniques, can be used for disease diagnosis.

[0182] More advantageously, the luminescent molecules according to the present invention are tunable. Surprisingly, it has been found that modification of the R group provides a series of luminescent compounds that require the same excitation wavelength but exhibit different emission spectra. Even more advantageously, the luminescent compounds of the present invention can be designed to emit wavelengths spanning the entire visible spectrum by changing the structure of the R group.

[0183] In addition, the luminescent compounds of the present invention can be used in multiplex systems. For example, two or more luminescent molecules according to the present invention can be conjugated to corresponding second substances. The luminescent molecules can be excited at the same wavelength but emit at different wavelengths. This makes it possible to study two different second substances, such as biomolecules, in a biological system while using a single light source. For example, two or more different luminescent compounds according to the present invention can be used, for example, to observe or track two different second substances, such as biomolecules, in an in vivo or in vitro observation or tracking system.

[0184] It has also been surprisingly found that the luminescent compounds of the present invention can be used together with multiphoton excitation microscopy. As is known in the art, in multiphoton microscopy (also referred to as two-photon microscopy), for each excitation, light of two or more photons is absorbed. This technology is different 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 irradiating a luminescent compound, such as a conjugated luminescent compound, with a light source emitting a wavelength within the range of 500nm to 1000nm or 800nm ​​to 900nm. The use of multiphoton microscopy is advantageous because it uses lower energy light and therefore causes less damage to biological samples. Advantageously, when luminescent molecules are used in living systems, this prevents or mitigates phototoxicity. More advantageously, light penetrates deeper into the tissue and is less likely to photobleach from the luminescent compound.

[0185] The one or more luminescent compounds may emit light in the visible spectrum, ie, between 380 nm and 750 nm, and / or may exhibit a wavelength between 8000 cm -1 Up to 25,000cm -1 between, for example, 15,000 cm -1 Up to 25,000cm -1 In an embodiment, the one or more luminescent compounds may exhibit a Stokes shift of 5.0x10 -13 S cm -1 and 1.5x10 -11 S cm -1 between, for example, 6x10 -12 S cm -1 and 1.5x10 -11 S cm -1 When irradiated at 350 nm, the one or more luminescent compounds may exhibit a conductivity value between 1.5 x 10 -10 S cm -1 and 1x10 -3 S cm -1 between, for example, 1x10 -8 S cm-1 and 1x10 -3 cm -1 The photoconductivity between .

[0186] The light-emitting compound of the present invention may be any one of those compounds shown in Examples of the present invention, that is, any one or a combination of Compounds 38 to 43.

[0187] Therefore, another aspect of the present invention provides a luminescent molecule represented by the following general formula:

[0188]

[0189] wherein R represents an aromatic group and / or an aliphatic group;

[0190] p is an integer of 1 or 2;

[0191] q and s are independently an integer of 1, 2, 3 or 4;

[0192] Y 1 、Y 2 and Y 3 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 comprising 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;

[0193] Y 1 、Y 2 and / or Y 3 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0194] In an embodiment, the luminescent compound is a triphenylene derivative, that is, the luminescent compound comprises a triphenylene core. In an embodiment, the luminescent compound comprises a core comprising a polycyclic aromatic hydrocarbon, for example, comprising five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, or twenty or more fused six-membered rings. For example, the luminescent compound may comprise a core comprising a polycyclic aromatic hydrocarbon comprising six fused six-membered rings.

[0195] In an embodiment, the luminescent molecule is represented by the following general formula:

[0196]

[0197] wherein R represents an aromatic group and / or an aliphatic group;

[0198] Y 4 、Y5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 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 comprising 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;

[0199] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 Two or more of the can be combined together to form a fused ring (eg, a fused aromatic ring).

[0200] In an embodiment, Y 1 To Y 13 One or more or all of can represent or comprise alkyl groups.The one or more alkyl groups can be straight or linear chains, or can comprise branched chains, and / or can be further functionalized.The alkyl chain can comprise 1 to 20 carbon atoms, for example 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.

[0201] Additionally or alternatively, Y 1 To Y 3 or Y 4 To Y 13 may independently represent or include an aryl group. The one or more aryl groups may be unsubstituted or may be further functionalized. In an embodiment, Y 1 To Y 3 or Y 4 To Y 13The polyether chain or polyglycol chain may independently represent or comprise a polyether chain or polyglycol group, such as a polyethylene glycol moiety. The polyether chain or polyglycol chain may comprise a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0202] In an embodiment, Y 1 To Y 3 or Y 4 To Y 13 One or more or all of may independently represent or contain an alkoxy group, such as an OR' group, wherein R' is a linear or branched alkyl chain. 1 To Y 3 or Y 4 To Y 13 One or more or all of may comprise or consist of a linear alkoxy group selected, for example, from OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 One or more of alkyl groups.

[0203] In an embodiment, Y 5 、Y 6 、Y 9 、Y 10 、Y 13 One or more or all of each represent a hydrogen atom.

[0204] 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 Can each represent OC5H 11 group.

[0205] In an embodiment, the luminescent compound is represented by the following general formula:

[0206]

[0207] where R 1 and R 2 independently represent an aromatic group and / or an aliphatic group;

[0208] p and q are independently integers from 1 to 2;

[0209] s is an integer from 1 to 4;

[0210] Y 1 、Y 2 and Y 3 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 comprising 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;

[0211] Y 1 、Y 2 or Y 3 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0212] In an embodiment, the luminescent compound is represented by the following general formula:

[0213]

[0214] where R 1 、R 2 、R 3 independently represent an aromatic group and / or an aliphatic group;

[0215] p, q and s are each independently an integer from 1 to 2;

[0216] Y 1 、Y 2 and Y 3 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 comprising 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.

[0217] Preferably, R 1 、R 2 、R 3 represents the same type of group, such as R 1 、R 2 、R 3 may each represent a naphthyl group.

[0218] In an embodiment, the luminescent compound may be represented by the following general formula:

[0219]

[0220] wherein R independently represents an aromatic group and / or an aliphatic group;

[0221] q is independently an integer from 1 to 3;

[0222] s is independently an integer from 1 to 4;

[0223] t is independently an integer from 1 to 4;

[0224] Y 2 、Y 3 and Y 14 and 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 comprising 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;

[0225] Y 2 、Y 3 and / or Y 14 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0226] In an embodiment, the luminescent compound may be represented by the following general formula:

[0227]

[0228] wherein R independently represents an aromatic group and / or an aliphatic group;

[0229] Y 15 、Y 16 、Y 17 、Y 18 、Y 19 、Y 20 、Y 21 、Y 22 、Y 23 、Y 24 、Y 25 、Y 26independently 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 comprising 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;

[0230] 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 amines are combined together to form a fused ring (eg, a fused aromatic ring).

[0231] 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 Can independently represent or include alkyl groups. Said one or more alkyl groups can be straight or linear chains, or can include branches, and / or can 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 one or more aryl groups may be unsubstituted or may be further functionalized. In an embodiment, Y 15 、Y 16 、Y 17 、Y 18 、Y 19 、Y 20 、Y 21 、Y 22 、Y23 、Y 24 、Y 25 、Y 26 The polyether or polyglycol groups may independently represent or include a polyether chain or a polyglycol group, such as a polyethylene glycol moiety. The polyether or polyglycol chain may include a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0232] 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 of may independently represent or include an alkoxy group, for example an OR' group, wherein R' is a linear or branched alkyl chain. The alkyl chain may contain 1 to 20 carbon atoms, for example 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.

[0233] 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 may contain a linear alkoxy group, for example, selected from OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 One or more of the alkyl groups.

[0234] In an embodiment, Y 16 、Y 19 、Y 22 、Y 23 、Y 26 One or more or all of each represent a hydrogen atom.

[0235] 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 Can each represent OC5H 11 Group. For example, Y 17 、Y 18 may each represent an OCH3 group.

[0236] For example, Y 16 、Y 19 、Y 22 、Y 23 、Y 25 Each represents a hydrogen atom, Y 15 、Y 20 、Y 21 、Y 24 、Y 25 Each represents OC5H 11 Group, Y 17 、Y 18 Represents an OCH3 group.

[0237] Another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0238]

[0239] wherein R represents an aromatic group and / or an aliphatic group;

[0240] J 1 、J 2 、J 3 、J 4 、J 5independently 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 comprising 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;

[0241] Among them J 1 and J 2 or J 3 and J 4 can be combined to form fused rings (e.g., fused aromatic rings);

[0242] 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.

[0243] In all embodiments, the term "fused ring" is intended to define groups bonded together to form a ring (eg, an aromatic ring and / or a heterocyclic ring) that forms part of the core of the emissive compound, ie, expands the triphenylene core.

[0244] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0245]

[0246] wherein R represents an aromatic group and / or an aliphatic group;

[0247] J 6 、J 7 、J 8 、J 9 、J 10 、J 11 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 comprising 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;

[0248] Among them J 6 and J 7 and / or J 8 and J 9 can be combined to form fused rings (e.g., fused aromatic rings);

[0249] A6 、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.

[0250] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0251]

[0252] where R 1 and R 2 independently represent an aromatic group and / or an aliphatic group;

[0253] J 12 、J 13 、J 14 、J 15 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 comprising 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;

[0254] Among them J 12 and J 13 can be combined to form fused rings (e.g., fused aromatic rings);

[0255] 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.

[0256] Still another aspect of the present invention provides a light-emitting compound represented by the following general formula:

[0257]

[0258] where R 1 、R 2 、R 3 independently represent an aromatic group and / or an aliphatic group;

[0259] 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 comprising 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;

[0260] 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.

[0261] In the embodiment, A 1 To A 18 One or more or all of may contain alkyl groups. The one or more alkyl groups may be straight or linear chains, or may contain branches, and / or may be further functionalized. Additionally or alternatively, A 1 To A 18 Aryl groups may be included independently. The one or more aryl groups may be unsubstituted or may be further functionalized.

[0262] In the embodiment, A 1 To A 18 One or more or all of may comprise or consist of a linear alkyl group, for example selected from CH3, C2H5, C3H7, C4H9, C5H 11 、C6H 13 、C7H 15 、C8H 17 、C9H 19 or C 10 H 21 One or more of the alkyl groups.

[0263] In the embodiment, A 1 To A 18 One or more or all of the alkylene groups may independently comprise a polyether chain or polyglycol group, such as a polyethylene glycol moiety. The polyether chain or polyglycol chain may comprise a total of 1 to 20 carbon atoms and oxygen atoms, such as 2 to 18 carbon atoms and oxygen atoms, 3 to 17 carbon atoms and oxygen atoms, 4 to 16 carbon atoms and oxygen atoms, 5 to 15 carbon atoms and oxygen atoms, 6 to 14 carbon atoms and oxygen atoms, 7 to 13 carbon atoms and oxygen atoms, 8 to 12 carbon atoms and oxygen atoms, or 9 to 11 carbon atoms and oxygen atoms.

[0264] In an embodiment, J or J 1 To J 15One or more or all of may independently represent hydrogen atoms. In an embodiment, A or A 1 To A 18 One or more or all of may independently represent a linear or branched alkyl group. 1 To A 18 One or more or all of may independently represent a linear alkyl chain containing 1 to 20 carbon atoms, for example 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1 carbon atoms. In an embodiment, A or A 1 To A 18 One or more or all of them can independently represent CH3, C2H5, C3H7, C4H9, C5H 11 、C6H 13 、C7H 15 、C8H 17 、C9H 19 and / or C 10 H 21 .

[0265] 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 Each represents an alkyl chain, such as C5H 11 part.

[0266] For example, in an embodiment, J 6 To J 11 Each represents a hydrogen atom, and A 6 To A 11 Each represents an alkyl chain, such as C5H 11 part.

[0267] In an embodiment, R, R 1 、R 2 or R 3 It can be an alkyl group, such as a straight or branched alkyl chain. In an embodiment, R, R 1 、R 2 、R 3 At least one of the groups may be a methyl, ethyl, propyl or butyl group.

[0268] In an embodiment, R, R 1 、R 2 or R3 In the embodiment where the aromatic group is present, the aromatic group may be one or a combination of an aromatic hydrocarbon group and / or an aromatic heterocyclic group.

[0269] In R, R 1 、R 2 or R 3 In the embodiment of aromatic hydrocarbon group, the aromatic hydrocarbon group can include one or combination in the phenyl ring and / or substituted phenyl ring.On the phenyl ring, one, two, three, four or five other substituents can be present.The substituent is directly bonded to the phenyl ring and can be one or combination in the following groups: fluorine, chlorine, bromine, iodine, hydroxyl group, amine group, nitro group, alkoxy group, carboxylic acid, amide, cyano group, trifluoromethyl, ester, alkene, alkynes, azide, azo, isocyanate, ketone, aldehyde, the alkyl group consisting of hydrocarbon chain or hydrocarbon ring, the alkyl group consisting of other heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, nitrogen and / or sulphur.The alkyl group can include for example hydroxyl group, amine group, nitro group, ether group, carboxylic acid, amide, cyano group, trifluoromethyl, ester, alkene, alkynes, azide, azo, isocyanate, ketone, aldehyde.The substituent can be another aromatic group, for example, and R can include the phenyl substituted by another phenyl ring. In an embodiment, the R group can be a benzene ring substituted with a second benzene ring, which in turn is substituted with a third benzene ring. 1 、R 2 or R 3 It can represent a p-fluorophenyl group, an m-fluorophenyl group, an o-fluorophenyl group, a thienyl 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-substituted, di-substituted, or tri-substituted aminophenyl moiety), a nitrophenyl moiety (e.g., a p-nitrophenyl moiety), or a phenol moiety.

[0270] In R, R 1 、R 2 or R 3 In embodiments where the aromatic group is an aromatic group, the aromatic group can be a polycyclic aromatic hydrocarbon, such as naphthalene, anthracene, phenanthrene, tetracene, lettuce, triphenylene, pyrene, pentacene, benzo[a]pyrene, corannulene, benzo[ghi]perylene, coronene, ovalene, fullerene and / or benzo[c]fluorene. The R group can be bonded to a triphenylene derivative through any isomer of the polycyclic aromatic hydrocarbon, such as 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.

[0271] In R, R 1 、R2 or R 3 In embodiments where the heterocyclic group is an aromatic heterocyclic group, the heterocyclic group may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a nine-membered ring, a ten-membered ring, or a fused ring. In embodiments, the heterocyclic group may 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, quinazoline, pyridazine, cinnoline, phthalazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, pyridine, or thiophene.

[0272] In R, R 1 、R 2 or R 3 In embodiments where the aliphatic group is an aliphatic group, the aliphatic group can be one or a combination of the following groups: a normal alkyl chain, a branched alkyl chain, an alkyl chain containing an unsaturated moiety, an alkyl chain containing heteroatoms such as fluorine, chlorine, bromine, iodine, oxygen, sulfur, or nitrogen. The alkyl chain can contain an unsaturated moiety (including an olefin) or an aromatic moiety. The alkyl chain can contain a functional group for further derivatization of a polycyclic aromatic hydrocarbon (e.g., triphenylene) derivative. For example, the functional group can be one or more of an azide, a carbonyl group, an alcohol, a halogen, an olefin, or a thioacetate.

[0273] In an embodiment, R, R 1 、R 2 or R 3 Contains crown ether.

[0274] Within the scope of this application, it is clearly intended that the various aspects, embodiments, examples and alternatives set forth in the preceding paragraphs, in the claims and / or in the following description and drawings, and in particular, their individual features can be adopted independently or in any combination. That is, all embodiments and / or the features of any embodiment can be combined in any manner and / or combination unless such features are incompatible. For the avoidance of doubt, the terms "may", "and / or", "e.g.", and / or "for example", and any similar terms as used herein, should be interpreted as non-restrictive, so that there is no need for any such described features. In fact, any combination of optional features can be clearly envisioned without departing from the scope of the present invention, regardless of whether these features are explicitly claimed. The applicant reserves the right to change any originally submitted claims or to submit any new claims, including the right to amend any originally submitted claims to be subordinate to and / or incorporate any features of any other claims (although the original claims were not proposed in this way).

[0275] To further illustrate the present invention, reference is also made to the following non-limiting examples, with reference to the accompanying drawings:

[0276] Figure 1 is a table showing the structures of light-emitting compounds according to embodiments of the present invention;

[0277] Figure 2 is a synthetic route for producing precursors of compounds according to embodiments of the present invention;

[0278] Figure 3 are the absorption and emission spectra of compound 39;

[0279] Figure 4 is a schematic route for conjugating an antibody to a luminescent compound according to one embodiment of the present invention;

[0280] Figure 5 is a series of spectra showing conjugation of an antibody to a luminescent compound according to one embodiment of the present invention;

[0281] Figure 6 is a series of images showing conjugation of an antibody to a luminescent compound according to one embodiment of the present invention; and

[0282] Figure 7 is Compound 44 according to another embodiment of the present invention.

[0283] Now refer to Figure 2 , shows the synthetic route for the precursors used to produce compounds according to the examples of the present invention. Compounds 38 to 43 are synthesized from precursor 8, which in turn is synthesized from compound 3, which in turn is synthesized from precursor 2.

[0284] Precursor 2 was prepared according to the method described by N. Boden et al., J. Mater. Chem., 1995, 5, 2275.

[0285] Synthesis of compound 3

[0286] 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. under N2 for 20 minutes. A solution of precursor 2 (100 mg; 0.131 mmol) in PhMe (2 mL) was added and heated under reflux for 48-72 hours while stirring. The solution was cooled to room temperature and diluted with CH2Cl2 (20 mL). The organic phase was washed with aqueous NaOH (1 M; 2×20 mL), separated, and the organic phase was dried under vacuum. The crude black solid was purified by flash column chromatography (silica; 40% CH2Cl2: 60% n-hexane) to give compound 3 (35 mg; 32%) as a yellow solid.

[0287] The name of compound 3 is 8-(naphthalen-2-yl)-2,3,6,11,12-penta(pentyloxy)tribenzo[1,2-d]oxazole.

[0288] Compound 3 has the following characterization data: 1 H NMR (300MHz, CDCl3) δH: 10.22 (1H, s), 8.89 (1H, s), 8.49 (1H, dd, J 8.6, 1.7), 8.05-7.99 (2H, m), 7.96-7.91 (5H, m), 7.62-7.59 (2H, m), 4.54 (2H, t, J 6.8), 4.51 (2H, t, J 6.8), 4.32-4.25(6H,m), 2.17-1.93(10H,m), 1.76-1.42(20H,m), 1.06-0.97(15H,m)ppm. 13 C NMR (100MHz, CDCl3) δC: 161.7, 149.8, 149.3, 149.0, 148.6, 143.2, 140.9, 140 .6, 135.0, 133.4, 129.3, 128.9, 128.3, 128.0, 127.9, 127.4, 127.2, 125.0, 125 ppm. MALDI+ m / z: 825.5 ([M]+100%). IR λ-1 (pure): Elemental analysis found: C, 78.95; H, 8.02; N, 1.83%. 54 H 67NO6 requires C, 78.51; H, 8.17; N, 1.70%.

[0289] Synthesis of precursor 8

[0290] Precursor 8 is synthesized using the following method. 8-(naphthalene-2-yl)-2,3,6,11,12-penta(pentyloxy)tribenzo[1,2-d]oxazole (compound 3) (150 mg, 0.18 mmol, 1 eq) is dissolved in CH2Cl2 (10 mL), dried and degassed in a 2-necked flask equipped with subaseal for 10 minutes, and purged with N2 for 10 minutes. The green solution is stirred at -10°C under N2 for 10 minutes, and boron tribromide (1M CH2Cl2 solution) (0.2 mmol, 1.1 eq) is added via a syringe through subaseal. The black solution is stirred at -10°C for 2 hours, then poured onto crushed ice and stirred until all ice melts. The product is then extracted with ethyl acetate (20 mL), washed with water (3 × 50 mL) and evaporated to dryness to obtain 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-tetra(pentyloxy)tribenzo[1,2-d]oxazol-11-ol (31 mg, 23%) as a yellow solid.

[0291] The name of precursor 8 is 8-(naphthalen-2-yl)-2,3,6,12-tetra(pentyloxy)tribenzo[1,2-d]oxazol-11-ol.

[0292] Precursor 8 has the following characterizing data. 1 H NMR 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 δ C(100MHz, CDCl3)161.7, 149.4, 148.9, 146.0, 145.3, 143.0, 140.9, 140.2, 13 4.8, 133.2, 129.1, 128.66, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 1 24.7, 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, 14.2ppm. MALDI m / z: 755.65([M] + 100%), 756.66 ([M+H] + 70%), 757.67 ([M+1+H] + 25%).

[0293] Example 1-Synthesis of Compound 38

[0294] Compound 38 is synthesized by the following method.With precursor 8 (100mg, 0.13mmol) and K CO (114mg, 0.83mmol) slurries in DMF (5mL) are using CaCl In the case of drying tube, reflux 0.5 hour, then add 2-(2-(2-chloroethoxy) ethyoxy) methyl acetate (114mg, 0.40mmol) and KI (75mg, 0.5mmol).Gained slurries are further refluxed 3 hours.Reaction mixture is cooled to room temperature, and leach precipitate via suction filtration.Vacuum evaporation solvent from filtrate is to dry, and thick solid is passed through via flash column chromatography (silicon dioxide, 25%EtOAc: 75% normal hexane) purifying to purify, obtain compound 38 (36mg, 30%) as yellow solid.

[0295] The name of compound 38 is methyl 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetra(pentyloxy)tribenzoylene[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetate.

[0296] Compound 38 has the following characterization data: 1 H 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,J6.7), 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 ,123.6,123.3,116.5,112.7,108.1,107.1,103.7,103.6,71.8,71.4,71.2,70.4,69.8 , 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, 14.2ppm. MALDI m / z: 915.7([M] + 100%), 916.7 ([M+H] + 90%). Elemental analysis found: C, 73.41; H, 7.56; N, 1.54%. 56 H 69 NO 10 Required C, 73.42; H, 7.59; N, 1.53%.

[0297] Example 2-Synthesis of Compound 39

[0298] Compound 39 was synthesized using the following method. A solution of NaOH (3 mg, 0.08 mmol) in H o (1 mL) was added to a solution of compound 38 (35 mg, 0.04 mmol) in MeOH (5 mL). The resulting solution was heated at reflux for 5 hours. The reaction mixture was cooled to room temperature and an aliquot of the 1M HCl aqueous solution was added until no precipitate was formed. The precipitate was collected by suction filtration to obtain a yellow solid (24 mg, 70%).

[0299] The name of compound 39 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetra(pentyloxy)tribenzoylene[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)acetic acid.

[0300] Compound 39 has the following characterization data: 1 H NMR 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, 13 3.1, 129.1, 128.7, 128.0, 127.9, 127.6, 127.2, 126.8, 124.8, 124.7, 124.6, 124.0, 12 3.6, 123.3, 116.5, 112.7, 108.1, 107.1, 103.7, 103.6, 71.8, 71.4, 71.2, 70.4, 69.8, 6 9.8, 69.7, 69.0, 68.5, 29.4, 29.3, 29.2, 28.6, 28.5, 28.4, 22.8, 22.7, 14.3, 14.2ppm. MALDI m / z: 901.5([M] + 100%), 902.5 ([M+H] + 70%). Elemental analysis found: C, 73.24; H, 7.52; N, 1.54%. 55 H 67 NO 10 Required C, 73.23; H, 7.55; N, 1.55%.

[0301] Now refer to Figure 3 , shows spectrum 30. Shown are the absorption spectrum 31 and emission spectrum 32 of compound 39 in ethyl acetate.

[0302] Example 3-Synthesis of Compound 40

[0303] Compound 40 is synthesized using the following method.By precursor 8 (100mg, 0.13mmol) and K cO (37mg, 0.26mmol) slurries in MeCN (5mL) at CaCl in the case of drying tube, refluxed 0.5 hour, then add 4-methylbenzenesulfonic acid 2-(2-(2-azidoethoxy)ethoxy)ethyl ester (87mg, 0.26mmol).Gained slurries were further refluxed 24 hours.Reaction mixture was cooled to room temperature, and filtered out precipitate via suction filtration.Vacuum evaporation solvent from filtrate is to dry, and thick solid is passed through via flash column chromatography (silicon dioxide, 25%EtOAc: 75% normal hexane) purifying to purify, obtain compound 38 (18mg, 15%) as yellow solid.

[0304] The name of compound 40 is 11-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)-8-(naphthalen-2-yl)-2,3,6,12-tetra(pentyloxy)tribenzo[1,2-d]oxazole.

[0305] Compound 40 has the following characterization data: 1 H NMR 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 ,129.1,128.7,128.0,127.9,127.6,127.1,126.9,124.8,124.7,124.6,124.0,123.6,1 23.4, 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, 14.21ppm. MALDI m / z: 912.9([M] + 100%), 913.9 ([M+H] + 90%). Elemental analysis found: C, 73.36; H, 7.55; N, 6.12%. 55 H 68 N4O8 requires C, 73.34; H, 7.51; N, 6.14%.

[0306] Example 4-Synthesis of Compound 41

[0307] Compound 41 is synthesized using the following method. By precursor 8 (100mg, 0.13mmol) and K CO (37mg, 0.26mmol) slurries in MeCN (5mL) at CaCl In the case of drying tube, reflux for 0.5 hour, then add 4-methylbenzenesulfonic acid 2-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrroles-1-yl) ethoxy) ethoxy) ethyl ester (101mg, 0.26mg). The gained slurries are further refluxed for 24 hours. The reaction mixture is cooled to room temperature, and precipitate is filtered out via suction filtration. From the filtrate, vacuum evaporation of solvent is to dryness, and thick solid is passed through via flash column chromatography (silicon dioxide, silicon dioxide, 50%EtOAc: 50% normal hexane) purifying to purify, obtain compound 38 (15mg, 13%) as a yellow solid.

[0308] The name of compound 41 is 2-(2-(2-((8-(naphthalen-2-yl)-2,3,6,12-tetra(pentyloxy)tribenzoylene[1,2-d]oxazol-11-yl)oxy)ethoxy)ethoxy)ethan-1-amine.

[0309] Compound 41 has the following characterization data: 1 H NMR 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, 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, 72.3, 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, 14.2ppm. MALDI m / z: 886.5([M] + 100%), 887.6 ([M+H] + 70%).

[0310] Example 7 - Use of Compound 39 as a Biosensor with Antibodies

[0311] Now refer to Figure 4 , shows a schematic route 3 for conjugating antibody A to a luminescent compound LC to produce conjugated antibody A-LC according to one embodiment of the present invention.

[0312] The luminescent compound LC used in this example is compound 39. Compound 39 was activated for conjugation as follows. A solution containing the following components was prepared:

[0313] 10 μL of compound 39, dissolved in DMSO at a concentration of 3.8 mg / ml (4.2 mM);

[0314] 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);

[0315] 1 μL triethylamine, to a final concentration of 0.67 μL / mL (6.6 μM).

[0316] The resulting solution was kept at room temperature on a shaking incubator for 20 minutes, generating a "biosensor solution" containing the luminescent compound, compound 39, which contains an NHS (N-hydroxysuccinimide) ester instead of a carboxylic acid functional group.

[0317] Antibody A was prepared as follows. 50 μL of antibody (2 mg / mL (approximately 14 μM)) was added to an Amicon (RTM) Ultra-0.5 ml filter set containing a 30 kDa cutoff filter. The antibody buffer was exchanged into 0.1 M sodium borate buffer (pH 8.5) using two rounds of dilution / concentration with the addition of 400 μL of borate buffer to produce an "antibody solution."

[0318] Antibody A was conjugated to the luminescent compound LC as follows. The "antibody solution" and "biosensor solution" were directly combined and allowed to react at room temperature for 1 hour. The resulting conjugated antibody A-LC was purified from unreacted luminescent compound using a standard desalting column (ZebaSpin, 7 kDa MWCO), and the labeled conjugate was characterized by UV-vis spectroscopy.

[0319] Now refer to Figure 5 , shows a series of spectra showing the conjugation of Antibody A with a luminescent compound LC according to this embodiment of the present invention. Spectrum 51 is taken from Antibody A alone. Spectrum 52 is taken from the luminescent compound LC (Compound 39) alone. Spectrum 53 is taken from Antibody A-LC conjugated to the luminescent compound.

[0320] Now refer to Figure 6 , shows a series of images showing the conjugation of the antibody according to this embodiment of the present invention with a luminescent compound. Image 61 is an image of the luminescent compound LC alone, Image 62 is an image of a control sample containing an antibody conjugated to Alexa 488 (RTM) according to a comparative embodiment of the present invention, and Image 63 is an image of the antibody A-LC conjugated to the luminescent compound according to Example 7 of the present invention.

[0321] Example 8-Synthesis of Compound 44

[0322] 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 and maintained at reflux under N for 18 hours. The reactants were cooled to room temperature and then evaporated to dryness in vacuo and purified by flash column chromatography (silica, 60% CH2Cl2: 40% n-hexane) to give the intermediate (19 mg, 18%) as a brown solid.

[0323] The intermediate (3-fluoro-N-(2,3,6,7,10,11-hexa(pentyloxy)triphenylene-1-yl)benzamide) (100 mg, 0.11 mmol) was dissolved in xylene (10 mL) and Woollins reagent (117.8 mg, 0.22 mmol) was added to the flask. The reaction was stirred at reflux for 24 hours and then cooled to room temperature, resulting in the formation of a gray precipitate. The contents of the flask were filtered through filter paper and the filtrate was recovered. The filtrate was evaporated to dryness and purified by column chromatography (silica, 40% dichloromethane:hexanes) and (silica, 1% acetone:hexanes) to give 8-(3-fluorophenyl)-2,3,6,11,12-penta(pentyloxy)tribenzo[1,2-d][1,3]selenazole (1.8 mg) as a yellow solid.

[0324] The name of compound 44 is 8-(3-fluorophenyl)-2,3,6,11,12-penta(pentyloxy)tribenzoylene[1,2-d][1,3]selenazole.

[0325] Compound 44 has 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] + ).

[0326] Those skilled in the art will appreciate that any number of combinations of the foregoing features and / or features shown in the accompanying drawings provide significant advantages over the prior art and are therefore within the scope of the invention described herein.

[0327] Some aspects and embodiments of the present invention are defined by the following clauses:

[0328] 1. A luminescent molecule represented by the following general formula:

[0329]

[0330] wherein R represents an aromatic group and / or an aliphatic group;

[0331] p is an integer of 1 or 2;

[0332] q and s are independently an integer of 1, 2, 3 or 4;

[0333] Y 1 、Y 2 and Y 3 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 comprising 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;

[0334] Y 1 、Y 2 and / or Y 3 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0335] 2. The luminescent molecule according to item 1, which is represented by the following general formula:

[0336]

[0337] wherein R represents an aromatic group and / or an aliphatic group;

[0338] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 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 comprising 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;

[0339] Y 4 、Y 5 、Y 6 、Y 7 、Y 8 、Y 9 、Y 10 、Y 11 、Y 12 、Y 13 Two or more of the can be combined together to form a fused ring (eg, a fused aromatic ring).

[0340] 3. A luminescent compound according to any preceding clause, wherein Y 1 To Y 13 One or more or all of represent or contain an alkyl group, such as a linear alkyl group or a branched alkyl group.

[0341] 4. The luminescent 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, 4 to 16 carbon atoms.

[0342] 5. The luminescent compound according to item 3 or 4, wherein Y 1 To Y 3 or Y 4 To Y 13 One or more or all of independently represent an alkoxy group, such as an OR' group, wherein R' is a linear or branched alkyl chain.

[0343] 6. The luminescent compound according to item 5, wherein Y 1 To Y 3 or Y 4 To Y 13One or more or all of them are composed of straight chain alkoxy groups, and the straight chain alkoxy groups are selected from OCH3, OC2H5, OC3H7, OC4H9, OC5H 11 、OC6H 13 、OC7H 15 、OC8H 17 、OC9H 19 or OC 10 H 21 One or more or a combination of groups.

[0344] 7. The luminescent compound according to item 6, wherein Y 4 、Y 7 、Y 8 、Y 11 、Y 12 Each represents an alkoxy group, for example an OR' group.

[0345] 8. The luminescent compound according to clause 7, wherein Y 4 、Y 7 、Y 8 、Y 11 Each represents OC5H 11 group.

[0346] 9. The luminescent compound according to clauses 2 to 8, wherein Y 5 、Y 6 、Y 9 、Y 10 、Y 13 One or more or all of represent hydrogen atoms.

[0347] 10. A luminescent compound according to any preceding clause, which is represented by the following general formula:

[0348]

[0349] wherein R represents an aromatic group and / or an aliphatic group;

[0350] J 1 、J 2 、J 3 、J 4 、J 5 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 comprising 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;

[0351] Among them J 1and J 2 or J 3 and J 4 can be combined to form fused rings (e.g., fused aromatic rings);

[0352] 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.

[0353] 11. The luminescent compound according to item 10, wherein A 1 To A 5 One or more or all of contain an alkyl group.

[0354] 12. A luminescent compound according to clause 10 or 11, wherein the one or more alkyl groups consist of linear alkyl groups selected from the group consisting of CH3, C2H5, C3H7, C4H9, C5H 11 、C6H 13 、C7H 15 、C8H 17 、C9H 19 or C 10 H 21 One or more of the alkyl groups.

[0355] 13. A luminescent compound according to clause 10, 11 or 12, wherein J 1 To J 5 One or more of independently represent a hydrogen atom.

[0356] 14. The luminescent compound according to any one of clauses 10 to 13, wherein 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 Each represents an alkyl chain, such as C5H 11 part.

[0357] 15. The luminescent compound according to any preceding clause, which is represented by the formula of Compound 44 of the present specification.

[0358] 16. The luminescent compound according to item 1 or 2, which is represented by the following general formula:

[0359]

[0360] where R 1 and R 2 independently represent an aromatic group and / or an aliphatic group;

[0361] p and q are independently integers from 1 to 2;

[0362] s is an integer from 1 to 4;

[0363] Y 1 、Y 2 and Y 3 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 comprising 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;

[0364] Y 1 、Y 2 or Y 3 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0365] 17. The luminescent compound according to item 1 or 2, which is represented by the following general formula:

[0366]

[0367] where R 1 、R 2 、R 3 independently represent an aromatic group and / or an aliphatic group;

[0368] p, q and s are each independently an integer from 1 to 2;

[0369] Y 1 、Y 2 and Y 3 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 comprising 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.

[0370] 18. The luminescent compound according to item 1 or 2, which is represented by the following general formula:

[0371]

[0372] wherein R independently represents an aromatic group and / or an aliphatic group;

[0373] q is independently an integer from 1 to 3;

[0374] s is independently an integer from 1 to 4;

[0375] t is independently an integer from 1 to 4;

[0376] Y 2 、Y 3 and Y 14 and 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 comprising 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;

[0377] Y 2 、Y 3 and / or Y 14 They may be combined to form a fused ring (eg, a fused aromatic ring).

[0378] 19. The luminescent compound according to Item 18, which is represented by the following general formula:

[0379]

[0380] wherein R independently represents an aromatic group and / or an aliphatic group;

[0381] 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 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 comprising 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;

[0382] Y 15 、Y 16 、Y 17 、Y18 、Y 19 、Y 20 、Y 21 、Y 22 、Y 23 、Y 24 、Y 25 、Y 26 Two or more of the amines are combined together to form a fused ring (eg, a fused aromatic ring).

[0383] 20. The luminescent compound according to item 19, wherein 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, such as OC5H 11 group or OCH3 group.

[0384] 21. The luminescent compound according to item 19 or 20, wherein Y 16 、Y 19 、Y 22 、Y 23 、Y 26 One or more or all of each represent a hydrogen atom.

Claims

1. A luminescent compound represented by the following general formula: wherein X represents one of an oxygen atom, a sulfur 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 hydrogen atoms; A 1 、A 2 、A 3 、A 4 、A 5 independently represent hydrogen atoms, C 1-20 Alkyl groups, polyether groups; Among them A 1 、A 2 、A 3 、A 4 、A 5 One or more of the compounds comprises a functional group capable of forming a covalent bond with a second substance.

2. The luminescent compound of claim 1, wherein the functional group is selected from a carboxylic acid moiety, an ester, an azide, an amine, a maleimide, a thiol moiety, an isothiocyanate, an aldehyde, a ketone and / or an aliphatic alcohol.

3. The luminescent compound according to claim 1 or 2, wherein A 1 、A 2 、A 3 、A 4 、A 5 Four of the five independently expressed C 1-20 Alkyl group.

4. The luminescent compound according to claim 1, wherein A 1 、A 2 、A 3 、A 5 Each represents C 1-20 Alkyl group.

5. The luminescent compound according to claim 4, wherein the alkyl group is C5H 11 .

6. The luminescent compound according to claim 1, wherein A 1 、A 2 、A 3 、A 4 、A 5 One of the five includes or consists of a spacer and a functional group capable of forming a covalent bond with the second substance.

7. The luminescent compound according to claim 6, wherein A 4 The spacer comprises a functional group capable of forming a covalent bond with the second substance or consists of a spacer and a functional group capable of forming a covalent bond with the second substance. The light-emitting compound according to claim 6 , wherein the spacer comprises a continuous chain of 3 to 20 atoms. 9 . The luminescent compound according to claim 8 , wherein the spacer comprises a continuous chain of 3 to 20 atoms selected from carbon atoms or a combination of carbon atoms and heteroatoms.

10. The luminescent compound according to claim 9, wherein the spacer is a polyether moiety. The light-emitting compound according to claim 6 , wherein the functional group (FG) is provided at a terminal end of the spacer.

12. The light-emitting compound according to claim 11, wherein the spacer and the functional group consist of the following structure -O-(CH2CH2O)2CH2CH2FG or -O-(CH2CH2O)2CH2FG.

13. The luminescent compound according to claim 1, wherein X represents an oxygen atom, and J 1 、J 2 、J 3 、J 4 、J 5 independently represents a hydrogen atom. The light-emitting compound according to claim 1 , wherein R represents an aromatic group. The luminescent compound according to claim 14 , wherein the aromatic group is selected from a phenyl group, a substituted phenyl group, and a polycyclic aromatic hydrocarbon. The luminescent compound according to claim 15 , wherein the polycyclic aromatic hydrocarbon is a naphthalene group.

17. A luminescent compound, which is any one of the following compounds 38 to 43 The luminescent compound according to claim 1 , which is covalently bonded to a second substance. The luminescent compound according to claim 18 , wherein the second substance is selected from a small molecule, a solid support or a biomolecule.

20. The luminescent compound according to claim 19, wherein the biomolecule is selected from the group consisting of antibodies, proteins, and polynucleotides.

21. A kit of parts suitable for covalently bonding any one of the luminescent compounds according to claim 1 to a second substance, the kit of parts comprising one or more luminescent compounds according to claim 1 and a solvent suitable for dissolving or suspending the one or more luminescent compounds.

22. The kit of parts according to claim 21, wherein the second substance is a biomolecule.

Images