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Water-soluble near infrared luminescent quinoline squaraine dye and preparation and application thereof

A water-soluble, quinoline-based technology, applied in the direction of luminescent materials, azo dyes, organic dyes, etc., can solve the problems that the stability needs to be further improved, the application is hindered, and the emission wavelength range is not ideal.

Inactive Publication Date: 2009-09-30
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the extensive development and application of squaraine dyes, the demand standard for squaraine dyes will become higher and higher, but the existing cyanine dyes generally have poor solubility, low active bonding ability, and unsatisfactory emission wavelength range. , and the stability needs to be further improved, hindering its application in analysis, especially in biological analysis.

Method used

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  • Water-soluble near infrared luminescent quinoline squaraine dye and preparation and application thereof
  • Water-soluble near infrared luminescent quinoline squaraine dye and preparation and application thereof
  • Water-soluble near infrared luminescent quinoline squaraine dye and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Synthesis of water-soluble near-infrared luminescent squaraine dyes containing nitro-symmetric quinolines, whose molecular formula is: C 22 h 12 o 6 N 4 R 2 , the structural formula is:

[0092]

[0093] Among them, R=(CH 2 ) n COOH, n=0~7 integers, its properties are brown to dark brown solid, and its melting point is in the range of 330~356°C.

[0094] Add 10mL of concentrated nitric acid and 10mL of concentrated sulfuric acid to a 100mL three-necked flask equipped with a condenser, a thermometer, and a constant pressure dropping funnel under conditions of ice-water bath and magnetic stirring, and slowly add 2mL of 2-methylquinoline dropwise under full stirring to control The reaction temperature is below 10°C. After all the reactants are added, the reaction is continued for 4 hours, and the pH value is adjusted to 3-4 with NaOH solution in an ice-water bath. A large amount of white precipitates are formed. Suction filtration, and then use silica gel as a car...

Embodiment 2

[0101] Synthesis of water-soluble near-infrared luminescent squaraine dyes containing amino-symmetric quinolines. The molecular formula is: C 22 h 16 o 2 N 4 R 2 , the structural formula is:

[0102]

[0103] Among them, R=(CH 2 ) n COOH, n=0~7 integers, the properties are dark gray to brown solid, the melting point is in the range of 293~324°C.

[0104] In a 100mL three-necked flask, add 0.04mol iron powder and 40mL water, then add 2mL glacial acetic acid, boil on low heat for 5min under reflux conditions, cool slightly, add 0.01mol 5 or 6-nitro-2-methylquinoline dropwise , refluxed for 1h under stirring conditions, adding NaCO 3 Adjust to be alkaline, extract the organic phase with dichloromethane, distill under reduced pressure, remove the organic solvent (dichloromethane and a small amount of glacial acetic acid), and then separate by silica gel column chromatography [petroleum ether / ethyl acetate (1:4)] , to obtain the corresponding amino derivatives [5-amino-2...

Embodiment 3

[0108] Synthesis of water-soluble near-infrared luminescent squaraine dyes containing symmetrical quinolines with sulfonic acid groups. The molecular formula is: C 22 h 14 o 8 S 2 N 2 R 2 , the structural formula is:

[0109]

[0110] Among them, R=(CH 2 ) n COOH, n=0~7 integer, the property is black to dark brown solid, the melting point is in the range of 341~365℃.

[0111] A 100mL three-neck flask equipped with a condenser, a thermometer and a constant pressure dropping funnel was placed in an ice-water bath and magnetically stirred, and 20mL of concentrated sulfuric acid was slowly added dropwise with 2mL (0.016mol) of 2-methylquinoline under full stirring to control the reaction. The temperature was below 220°C. After all the reactants were added, the reaction was continued for 3h, and part of the sulfuric acid was neutralized with NaOH in an ice-water bath to make the pH ≈ 6.0, extracted with dichloromethane (20mL×5), the organic phases were combined, and the ...

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Abstract

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.

Description

technical field [0001] The invention belongs to the field of water-soluble near-infrared luminescent squaraine dye and its preparation and application, in particular to quinoline water-soluble near-infrared luminescent squaraine dye and its preparation and application. Background technique [0002] Since Triebs and Jacob first reported the synthesis of the first insoluble pyridine squaraine dye with pyridine and squaryl acid in 1965, squaraine dye has a unique D-π-A-π-D type conjugated system The zwitterionic structure has good photoelectric properties, such as strong absorbance (ε≥10 5 Lmol -1 cm -1 ), a wide range of absorption or emission wavelengths (from visible light to near-infrared regions), high light absorption coefficient, high luminescence quantum yield and good photostability have attracted the attention and attention of many scientists at home and abroad. The design and synthesis of new multifunctional squaraine dyes have been reported continuously, and have...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N33/53G01N21/64
Inventor 徐洪耀严正权陈玉风光善仪
Owner DONGHUA UNIV
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