54 results about "Squaraine dye" patented technology

The invention relates to a preparation method of a zinc oxide visible-light-induced photocatalyst sensitized by squarylium cyanine. The preparation method comprises the following steps: dissolving Zn(Ac)22H2O and glucose into deionized water; carrying out ultrasonic processing to form a settled solution; after transferring the solution into a liner of a polytetrafluoroethylene autoclave, performing hydrothermal reaction for 12 to 24 hours at a temperature of 140 to 180 DEG C; after cooling to room temperature, carrying out centrifugal washing on the obtained black powder respectively with the deionized water and absolute ethyl alcohol; drying at a temperature of 60 DEG C to obtain a zinc oxide and carbon composite precursor; placing the precursor into a muffle furnace to calcine for 3 hours at a temperature of 400 to 600 DEG C, so as to obtain zinc oxide microspheres; mixing the zinc oxide microspheres and the squarylium cyanine as well as an organic solvent; at a temperature of 30 to 60 DEG C, carrying out ultrasonic processing on the mixture for 0.5 to 2 hours; then removing the organic solvent under the condition of pressure reduction; and finally, drying the obtained solid at a temperature of 60 DEG C. The zinc oxide visible-light-induced photocatalyst sensitized by the squarylium cyanine can be used for photocatalysis processing on organic pollutants in air, soil and sewage.

A squarylium dye represented by formula (1):wherein A1 and B1 each independently represents a ring structure, and R1 and R2 each independently represents a substituent having a carbon number of 1 to 12.

The invention relates to water-soluble near infrared luminescent quinoline squaraine dye, of which the molecular structural general formula is shown on the figure. The method for preparing the water-soluble near infrared luminescent quinoline squaraine dye comprises that: firstly, 2-methylquinoline is subjected to bromination, sulfonation, nitration and acylation and reacts with acetonitrile and iodo-acid or iodo-ester to generate quinoline quaternary ammonium salt; and secondly, the quinoline quaternary ammonium salt is mixed with squaric acid, and the mixture is subjected to azeotropic distillation and dehydration, vacuum distillation and silica gel column chromatography and recrystallization through ethanol to obtain the water-soluble quinoline squaraine dye. The dye is applied in the fields of development of novel medicines, fluorescence labeling, probes, biological immunoassay, biological immunodetection and the like. The fluorescence-emission wavelength of the water-soluble quinoline squaraine dye is near infrared, so that the water-soluble quinoline squaraine dye has superior penetrability on environments and biological tissues and reduces self absorption and background absorption, and the sensitivity of fluorescence analysis can reach 10<-10> mol / L. The preparation method is simple and easy, has low cost and good economic benefit and is suitable for industrialized production.

The present invention relates to amphiphilic squaraine dyes of the general formula (1) as shown below Formula (1) wherein, R<1> = -(CH2-CH2-O)n-CH3, n = 4-8, or -(CH2)n-CO2X, n = 3-6, X = H, succinamide and R<2> = -CH3 or -(CH2-CH2-O)n-CH3, n = 4-8 and pharmaceutically acceptable derivatives thereof, for use as near infrared fluorescence probes in photodynamic diagnostic and biological, biochemical and industrial applications.

The invention provides a targeting material based on an indolium squarine dye, a preparation method thereof, a fluorescent nano-particle, and a preparation method of the fluorescent nano-particle. Bromine, hydrogen or methyl-substituted indolium squarine is coupled with targeting polypeptide RGD molecules or is respectively coupled with RDG molecules and an anticancer drug camptothecin to obtain amphiphilic diagnosis and treatment molecules. The molecules can be self-assembled in water to form the stable nano-particle with a uniform size. The nano-particle prepared in the invention can emit near infrared fluorescence, and can reduce the interference of background fluorescence and increase the signal penetrating depth in an in-vivo imaging process; the nano-particle has a tumor targeting performance, can be efficiently enriched in a tumor tissue are and can realize accurate in-vivo tumor fluorescence imaging; and the nano-particle has photodynamic properties, and can achieve effective photodynamic therapy or photodynamic therapy-chemotherapy combined therapy for tumors. So the nano-particle prepared in the invention has a good application prospect in the field of accurate diagnosisand treatment of cancers.

The present invention relates to a new kind of infrared absorbing squaraine cyanine dye as one new kind of compound containing quinoxalinone heterocycle in its structure. It has absorption wavelength of 700-1100 nm. It is prepared through condensation of squaric acid and quinoxalinone as precursor compound. It may be used in laser protection, fluorescent labeling, photoelectronic functional material and other fields.

The invention relates to the technical field of photocatalysis, particularly a squarylium cyanine dye sensitized titanium dioxide visible light catalyst, and a preparation method and application thereof. The preparation method comprises the following steps: mixing titanium dioxide with squarylium cyanine dye and an organic solvent, carrying out ultrasonic treatment on the mixture at 20-40 DEG C for 0.5-6 hours, wherein the ultrasonic frequency is 20-100kHz, and the ultrasonic power is 400-4000W; and drying the organic solvent by distillation to obtain the squarylium cyanine dye sensitized titanium dioxide visible light catalyst. The squarylium cyanine dye sensitized titanium dioxide visible light catalyst under the irradiation of visible light or sunlight can effectively degrade methylene blue and other organic wastewater pollutants, has high photocatalytic activity, and solves the technical problems of low visible light utilization ratio and low catalytic activity in the existing titanium dioxide photocatalyst. The preparation method provided by the invention has the advantage of simple technique, is easy to control and is suitable for industrial production and application.

Squaraine dyes are used to detect the presence of protein in a test sample, which is a substance that may contain protein. A squarine dye is placed in water, and in some instances joined with an aggregation agent, to create an aqueous dye solution. That dye solution is joined with a test sample. When the dye solution is joined with the test sample and the resultant test solution is excited by the application of photons, a resulting fluorescence or absence thereof reveals if protein was present in the test sample.

The invention designs and combines a squaraine dye with excellent performance, which is used in a dye-sensitized solar battery to obtain good performance test result of a photocell. An asymmetrical squaraine dye sensitizer used by the invention is compounded by adopting a fractional step method, the designed molecules are reasonable, and the molecule has high light stability. The compounded target product contains less by products, and is easy to separate and purify. All the designed squaraine dye molecules contain carboxyl, can form adsorption with the surface of a nanocrystalline film electrode, and have good application prospect in the photoelectric material field or the biomolecules detection field.

The invention provides benzpyrole squaric acid cyanine dye. The general formula of the structure of the benzpyrole squaric acid cyanine dye is shown in the description, wherein X is one of Br, Cl and I, and R is one of the following structures shown in the description. The benzpyrole squaric acid cyanine dye provided by the invention has good stability and large absorption strength, can be applied in matching reagents of a 5-classified hematology analyzer to be used as dye of nucleated red blood cells, and can also be applied to fluorescent marks and other life science research fields.

The invention discloses an adamantyl-modified near-infrared squaraine dye as well as a preparation method and application thereof. The preparation method comprises the following steps: (1) mixing an adamantine-modified aniline derivative with squaric acid, dissolving the mixture in proper solvents, connecting the solution with a water knockout drum, and carrying out reflux for several hours under the protection of N2; (2) cooling the reaction mixture obtained in the step (1) to the room temperature, and removing the solvents at reduced pressure, thus obtaining a crude product; (3) washing the crude product with petroleum ether for several times, and then purifying the product through silica gel column chromatography, thus obtaining the adamantyl-modified near-infrared squaraine dye product. The adamantyl-modified near-infrared squaraine dye and the preparation method have the prominent advantages that the squaraine dye has good stability and excellent optical property; the solubility of the dye in the water solution can be effectively improved after the squaraine dye is included by cyclodextrin; the squaraine dye can serve as a fluorescently and colorimetrically responsive pH probe; the 2-adamantyl-modified near-infrared squaraine dye is successfully applied to intracellular imaging of living cells so as to detect intracellular pH values.

The present invention relates to amphiphilic squaraine dyes of the general formula (1) as shown below Formula (1) wherein, R1=—(CH2—CH2—O)n—CH3, n=4-8, or —(CH2)n—CO2X, n=3-6, X=H, succinamide and R2=—CH3 or —(CH2—CH2—O)n—CH3, n=4-8 and pharmaceutically acceptable derivatives thereof, for use as near infrared fluorescence probes in photodynamic diagnostic and biological, biochemical and industrial applications.

An object of the present invention is to provide a drug delivery system capable of sustainedly releasing a drug noninvasively at any given point in time. The present invention relates to a liposome complex comprising a liposome membrane-constituting substance bonded to a light-absorbing compound having an absorption wavelength in the near-infrared region, selected from the group consisting of indocyanine green dyes, phthalocyanine dyes, squarylium dyes, croconium dyes, and diimmonium dyes.

The invention relates to synthesis of an amphiphilic indole squarylium cyanine dye and an application of the dye in the field of specific lysosome marking. In the invention, phenylhydrazine hydrochloride, of which a 4 position is substituted by bromine, hydrogen or methyl, is employed as a raw material to prepare the indole squarylium cyanine dye having the three substitutive groups and having carboxyl group functionalization, and then a condensation reaction between a carboxyl group and a primary amine is carried out to further introducing amino groups into the dye molecules. Ultraviolet absorption and fluorescent emission of the amphiphilic indole squarylium cyanine dye are both in near infrared region, so that interference due to background fluorescence in a bio-imaging process is reduced greatly. The dye is water-soluble so that the dye can be directly used in bio-imaging without any organic co-solvents, thereby achieving low bio-toxicity. The amino group in the dye is fully protonized under a lysosome acidic environment so that the electrostatic effect with lysosome membrane is more intensive. The dye can be used for marking the lysosome in living cells with marking time being capable of lasting for more than 48 h. It is the first time that the indole squarylium cyanine dye is applied in the field of lysosome marking.

The invention provides a squarylium cyanine dye and a preparation method therefor. The preparation method comprises the following steps: (1) firstly mixing a benzoindoles compound with squaric acid diethyl ester in an alcohol solvent, heating under the effect of triethylamine until reflux, reacting for 2-4 h, cooling, and carrying out suction filtration; (2) carrying out a reflux reaction on the product in the step 1) and malononitrile in the alcohol solvent under the effect of triethylamine, reacting for 10-30 min, washing with acetic acid, and carrying out suction filtration; and (3) heating the product in the step (2) and the benzoindoles compound with carboxyl in methylbenzene and n-butyl alcohol until reflux, and reacting for 7-10 h to obtain an end-product. The squarylium cyanine dye is relatively long in absorption and emission wavelength and good in light stability, active group carboxyl is introduced at the same time, and the squarylium cyanine dye can react with amino groups in biomolecules and is used for marking various biomolecules; and the synthetic method is simple, mild in condition and higher in yield, and provides good application prospects in the fields of molecular signature, fluorescence imaging and the like.

The invention discloses an asymmetric near-infrared squaraine dye, a preparation method thereof and an application thereof. According to the invention, an m-aminophenol derivative and the squaric acid are mixed to dissolve in an appropriate solvent, and then are subjected to the backflow water-diversion treatment in the nitrogen protection environment. After that, the resultant obtained reaction mixture is cooled to be at the room temperature and subjected to the decompression treatment to remove the solvent. The resultant crude product is purified through the silica gel column chromatography process to prepare the asymmetric near-infrared squaraine dye. According to the technical scheme of the invention, through introducing an oxygen-ether chain, the dissolvability of the squaraine dye in an aqueous solution can be effectively improved. The obtained asymmetric near-infrared squaraine dye is good in stability and excellent in optical performance, which can be used as a protein biomarker for dual responses of fluorescence reaction and colorimetric reaction. The asymmetric near-infrared squaraine dye can be applied in multiple fields of biological molecule marking, analyzing, separating, and the like.

The invention relates to a preparation method of a tin indium sulfide / squaraine composite visible light catalyst. The preparation method comprises the following steps: preparing tin indium sulfide, synthesizing indole squaraine dyestuff and preparing the tin indium sulfide / squaraine composite visible light catalyst. The preparation method provided by the invention has the beneficial effects that the preparation method is relatively simple and preparation conditions are easy to control; the prepared tin indium sulfide / squaraine composite visible light catalyst is a green, environment-friendly and high-performance catalyst, has no pollution and has high catalysis efficiency and certain application value.

The invention discloses a squaraine dye containing a benzothiazine structure and a preparation method thereof. The preparation method comprises the following steps: mixing a thiazine cyclic compound with squaric acid based on the mol ratio of 2:1; adding a mixed solvent of benzene and n-butyl alcohol; and under catalysis of 3-5ml of quinoline or pyridine, stirring and refluxing for 12-48h for carrying out condensation reaction to obtain the squarylium cyanine dye. In the invention, absorption wavelength for near-infrared absorption is 700-1100nm. The squaraine dye has excellent photo-thermal property, excellent chemical stability, good compatibility with organic matrix materials and small side effect on human body; the squaraine dye is a new type dye with excellent optical property; and the squaraine dye has wide application prospect in fields such as near-infrared laser protection, biomolecular fluorescence labeling, photoelectric functional materials, laser electrostatic copying materials, a dye laser and the like.

Photochemical acid progenitors in combination with dihydroperimidine squarylium dyes have been found to be particularly effective at generating acid upon irradiation with near-infrared radiation. It has been found that dihydroperimidine squarylium dyes that are particularly useful in this invention have an oxidation potential greater than about 0.5 V relative to SCE as measured in dichloromethane.

A squarylium dye represented by formula (1):wherein A1 and B1 each independently represents a ring structure, and R1 and R2 each independently represents a substituent having a carbon number of 1 to 12.

The invention discloses phenylboronic acid modified near-infrared squaraine dyes as well as a preparation method and application thereof. The preparation method comprises the following steps: mixing an indole-modified phenylboronic acid derivative with a dicyanyl vinyl squaraine derivative; carrying out dissolution, backflow, pressure-reduction evaporation-removal on a solvent and silica gel column chromatography purification to obtain the near-infrared squaraine dyes. The squaraine dyes have the advantages of better stability and excellent optical performance, in particular to contraposition-substituted phenylboronic acid groups; the squaraine dyes can be partially combined with cis-glycol in an ATP (adenosinetriphosphate) molecule, so that change of absorption spectrum and fluorescence spectrum of the dyes is induced through multiple electrostatic interactions among the dyes, the ATP and CTAB (Cetyl Trimethyl Ammonium Bromide), so that the dyes can be used as fluorescent probes for ATP detection, and the fluorescent probes are used for carrying out fluorescent imaging detection on the ATP in cells; moreover, the probes have the advantages of better biocompatibility and cellular permeability and lower biotoxicity, and has better detection sensitivity on ATP.

The invention relates to water-soluble near infrared luminescent quinoline squaraine dye, of which the molecular structural general formula is shown on the figure. The method for preparing the water-soluble near infrared luminescent quinoline squaraine dye comprises that: firstly, 2-methylquinoline is subjected to bromination, sulfonation, nitration and acylation and reacts with acetonitrile and iodo-acid or iodo-ester to generate quinoline quaternary ammonium salt; and secondly, the quinoline quaternary ammonium salt is mixed with squaric acid, and the mixture is subjected to azeotropic distillation and dehydration, vacuum distillation and silica gel column chromatography and recrystallization through ethanol to obtain the water-soluble quinoline squaraine dye. The dye is applied in the fields of development of novel medicines, fluorescence labeling, probes, biological immunoassay, biological immunodetection and the like. The fluorescence-emission wavelength of the water-soluble quinoline squaraine dye is near infrared, so that the water-soluble quinoline squaraine dye has superior penetrability on environments and biological tissues and reduces self absorption and background absorption, and the sensitivity of fluorescence analysis can reach 10<-10> mol / L. The preparation method is simple and easy, has low cost and good economic benefit and is suitable for industrialized production.

Provided are a squarylium dye having a carboxyindolenine structure and an N-alkyl substituent, and a photoelectric conversion element having high photoelectric conversion efficiency in a near-infrared region and a dye-sensitized solar cell, both of which are produced using the squarylium dye. The photoelectric conversion element or dye-sensitized solar cell uses a compound represented by the formula (1) as the squarylium dye. In the formula (1), R1 and R2 represent a substituted or unsubstituted C5 to C30 alkyl group; X represents C(CH3)2; and A and B represent a carboxy group.

The invention belongs to the technical field of squaraine dyes, and particularly relates to an indole squaraine dye and a preparation method and application thereof. The provided indole squaraine dyehas a structural formula shown in the formula (I), wherein R is a phenyl, an anthryl or a pyrenyl. The indole squaraine dye has a high molar extinction coefficient in the near-infrared region, has strong absorption in the near-infrared region, has obvious effects in sensitized singlet oxygen, can be used as a triplet photosensitizer, has a good application prospect in the field of photodynamic therapy, and can solve the problem that the existing squaraine dye has low quantum yield of the singlet oxygen in photodynamic therapy.

The invention relates to synthesis of an amphiphilic indole squarylium cyanine dye and an application of the dye in the field of specific lysosome marking. In the invention, phenylhydrazine hydrochloride, of which a 4 position is substituted by bromine, hydrogen or methyl, is employed as a raw material to prepare the indole squarylium cyanine dye having the three substitutive groups and having carboxyl group functionalization, and then a condensation reaction between a carboxyl group and a primary amine is carried out to further introducing amino groups into the dye molecules. Ultraviolet absorption and fluorescent emission of the amphiphilic indole squarylium cyanine dye are both in near infrared region, so that interference due to background fluorescence in a bio-imaging process is reduced greatly. The dye is water-soluble so that the dye can be directly used in bio-imaging without any organic co-solvents, thereby achieving low bio-toxicity. The amino group in the dye is fully protonized under a lysosome acidic environment so that the electrostatic effect with lysosome membrane is more intensive. The dye can be used for marking the lysosome in living cells with marking time being capable of lasting for more than 48 h. It is the first time that the indole squarylium cyanine dye is applied in the field of lysosome marking.

The invention relates to a method for preparing a trapezoidal broadband absorption carbene squaraine dye with a one-step method. The method comprises the following steps of: fully mixing functional carbine, a squaric acid, a ligand and a solvent at the room temperature; undergoing a reflowing reaction at the temperature of 60-130 DEG C for 10-120 hours; and after the reaction, purifying to obtain the carbene squaraine dye, wherein the mass ratio of the functional carbine to the squaric acid is (20-10):(4-1). The preparation method provided by the invention is easy and practicable, has a good economic benefit, and is suitable for industrial production; and the carbene squaraine dye prepared with the method can be widely applied in the fields of nonlinear optics, photodynamics therapy, optical database storage, laser printing, biological probes, near infrared mapping, solar cells, and the like.

Provided are a squarylium dye having a carboxyindolenine structure and an N-alkyl substituent, and a photoelectric conversion element having high photoelectric conversion efficiency in a near-infrared region and a dye-sensitized solar cell, both of which are produced using the squarylium dye. The photoelectric conversion element or dye-sensitized solar cell uses a compound represented by the formula (1) as the squarylium dye. In the formula (1), R1 and R2 represent a substituted or unsubstituted C5 to C30 alkyl group; X represents C(CH3)2; and A and B represent a carboxy group.

Fluorescent cyanine and squaraine dyes are described that can be conjugated to analyte molecules of interest such as peptides, proteins, nucleic acids, RNA, DNA, carbohydrates, polymers aid small molecules via a sulfonyl or sulfonamide substituent. The new dyes are made via a novel cyanine dye activation procedure that converts the normally stable, water solubilizing sulfonate substituents into a reactive sulfonyl halides. The sulfonyl halides may be directly conjugated to analytes or can be further converted to more stable reactive sulfonamide handles or to water soluble sulfonamides. The general structure of the new dyes is given below where the central linker is an unsaturated carbon chain or an unsaturated chain containing a squaraine moiety.

The present invention disclosed a squaraine dye of formula (I) and process for the preparation thereof. Further, the present invention disclosed to an electronic device comprising dye of formula (I).