Cyanine dye having azulene structure and preparation method thereof

A technology of cyanine dyes and alkyl groups, applied in the field of azulene-containing structural cyanine dyes and their preparation, can solve the problems of low conversion rate, poor reaction selectivity, difficult purification and the like, and achieves high conversion rate, good selectivity and easy purification. Effect

Inactive Publication Date: 2010-06-16
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] After comprehensive analysis, the existing cyanine dyes still have problems such as poor reaction selectivity, low conversion rate, and difficulty in purification.

Method used

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  • Cyanine dye having azulene structure and preparation method thereof
  • Cyanine dye having azulene structure and preparation method thereof
  • Cyanine dye having azulene structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The structural formula of the synthetic product:

[0044]

[0045] In a 250mL three-necked reaction flask with a mechanical stirrer and a condenser, add 1,3-diformyl azulene (18.4 g, 0.1 mol), 1-ethyl-2,3,3-trimethylindole iodide Salt (81.9 g, 0.26 mol) and acetic anhydride (100 mL), heated to reflux for 5 hours, cooled to room temperature, added water (200 mL) and stirred for 2 hours, and filtered the precipitated crystals.

[0046] The obtained crude product was dried, recrystallized with methanol, and filtered to obtain 57.6 g of green crystals with a yield of 74%.

[0047] The structure of the product was confirmed by NMR absorption:

[0048] 1H NMR (400MHz, DMSO-d 6 ): 1.42(t, 6H), 2.03(s, 12H), 4.26(m, 4H), 7.02(d, 2H), 7.11-7.20(m, 6H), 7.31-7.35(m, 2H), 7.54- 7.56 (m, 1H), 7.60 (d, 2H), 8.13 (s, 1H), 8.16 (d, 2H), 8.47 (d, 2H).

Embodiment 2

[0050] The structural formula of the synthetic product:

[0051]

[0052]In a 250mL three-necked reaction flask with a mechanical stirrer and a condenser, add 1,3-diformyl azulene (18.4 grams, 0.1 mol), 1-butyl-2,3,3-trimethylindole bromide Substitute salt (88.8 g, 0.3 mol) and acetic anhydride (150 mL), heated to reflux for 8 hours, cooled to room temperature, stirred, added water (250 mL), and filtered the precipitated crystals.

[0053] The obtained crude product was dried, recrystallized with ethanol, potassium fluoroborate (37.8 g) was added at the same time, heated to reflux for 2 hours, hot filtered, the filtrate was cooled to room temperature, and the precipitated crystals were filtered to obtain 50.0 g of green crystals, yield 63%.

[0054] The structure of the product was confirmed by NMR absorption:

[0055] 1H NMR (400MHz, DMSO-d 6 ): 0.94(t, 6H), 1.45(m, 4H), 1.76(m, 4H), 1.98(s, 12H), 4.22(t, 4H), 7.08(d, 2H), 7.18-7.29(m, 6H), 7.35-7.39 (m, 2H), 7.50-7.57...

Embodiment 3

[0057] The structural formula of the synthetic product:

[0058]

[0059] In a 250mL three-necked reaction flask with a mechanical stirrer and a condenser, add 1,3-diformyl-2,4,6-trimethylazulene (22.6 grams, 0.1 mol), 1-ethyl-2, 3,3-Trimethylindole iodide (113.4 g, 0.36 mol), pyridine (1 g), tert-butanol (100 mL) and benzene (50 mL), stirred, heated to reflux for 9 hours, cooled to room temperature, filtered to precipitate crystallization.

[0060] The obtained crude product was dried, recrystallized with ethanol, and potassium hexafluorophosphate (66 g) was added at the same time, heated to reflux for 1 hour, cooled to room temperature, and the precipitated crystals were filtered to obtain 58.2 g of green crystals with a yield of 68%.

[0061] The structure of the product was confirmed by NMR absorption:

[0062] 1H NMR (400MHz, DMSO-d 6 ): 1.50(t, 6H), 2.13(s, 12H), 2.67(s, 3H), 3.05(s, 6H), 4.28(m, 4H), 7.08(d, 2H), 7.14-7.26(m, 6H), 7.52 (s, 1H), 7.54 (d, 2H), 8.15...

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Abstract

The invention relates to a cyanine dye having an azulene structure, which has a molecular structure represented by a general formula below. The method for preparing the cyanine dye comprises the following steps: taking 1,3-dimethyl acyl azulene derivant and 1-alkyl-2,3,3-trimethyl indole salt as raw materials; performing condensation reaction in an inert solvent under the action of a condensing agent; and performing purification to obtain an objective product. The cyanine dye having the azulene structure has high purity, high yield, easy purification, large molar extinction coefficient and high solubility in organic solvents, is suitable for sensitive materials, CD recording media, infrared laser dyes and optical nonlinear materials, and is used for the fields of biomedicine and the like.

Description

technical field [0001] The invention belongs to the field of cyanine dyes, and more specifically relates to a cyanine dye containing an azulene structure and a preparation method thereof. Background technique [0002] Cyanine dyes have the characteristics of high photothermal stability, good solubility, large molar extinction coefficient, high reflectivity, low thermal conductivity, and large tunable range of maximum absorption wavelength. They can be widely used in photosensitive, optical disc recording media, infrared laser dyes, etc. , optical nonlinear materials and organic solar cells. In recent years, cyanine dyes have been increasingly used in various bioanalytical techniques, including DNA sequencing, fluorescent immunoassay detection, quantitative determination of biological macromolecules, and in situ fluorescent hybridization techniques. [0003] The current research results show that cyanine dyes have strong competitiveness in many fields and have broad developm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10
Inventor 王道林钱建华刘琳邢锦娟
Owner BOHAI UNIV
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