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High-selectivity red light absorption heptamethine cyanine dye as well as synthesis method and application thereof

A heptamethine, high-selectivity technology, applied in the direction of methine/polymethine dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of poor photostability and achieve less by-products and good red light selection Absorption performance, the effect of good selective absorption characteristics

Active Publication Date: 2021-08-13
上海戎科特种装备有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the longer the midline methazine chain (that is, the longer the conjugated chain), the worse the photostability

Method used

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  • High-selectivity red light absorption heptamethine cyanine dye as well as synthesis method and application thereof
  • High-selectivity red light absorption heptamethine cyanine dye as well as synthesis method and application thereof
  • High-selectivity red light absorption heptamethine cyanine dye as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0027] The present invention also proposes a method for synthesizing the heptamethine cyanine dye with high selective red light absorption as described above, comprising the following steps:

[0028] S1: Weigh 2,3,3-trimethyl-3H-indole-5 sulfonic acid potassium salt and p-benyl bromobenzoic acid in a molar ratio of 1:(1~1.05), dissolve them in acetonitrile, and inert Under the protection of the atmosphere, the reflux reaction was carried out to obtain the intermediate product Ⅰ;

[0029] S2: Weigh the intermediate product I, diethylamine, N,N'-dicyclohexylcarboimide and 4-dimethylaminopyridine at a molar ratio of 1:1.2:0.2:0.5, and weigh the intermediate product I Place diethylamine in a three-necked flask containing dichloromethane, then add N,N'-dicyclohexylcarboimide and 4-dimethylaminopyridine to fully react to obtain intermediate product II;

[0030] S3: Weigh the intermediate product II and 2-chloro-1-formyl-3-hydroxymethylenecyclohexene in a molar ratio of 1:(1-1.05), ...

Embodiment 1

[0068] This embodiment provides a heptamethine cyanine dye with highly selective red light absorption, the structural formula of the heptamethine cyanine dye is:

[0069]

[0070] This embodiment also provides a method for synthesizing the above-mentioned highly selective red-absorbing heptamethine cyanine dye, comprising the following steps:

[0071] S1: Accurately weigh 10mmol 2,3,3-trimethyl-3H-indole-5 sulfonic acid potassium salt and 10-10.5mmol p-Benyl bromobenzoic acid, dissolve them in 50ml acetonitrile, and protect them under a nitrogen atmosphere. Under reflux for 8 hours, cooled, rotary evaporated to remove acetonitrile, and washed with methyl tert-butyl ether or acetone several times, dried to obtain the intermediate product I.

[0072] S2: Accurately weigh 10mmol of the intermediate product I and 12mmol of diethylamine, place them in a three-necked flask containing 100ml of dichloromethane, then add 2mmol of N,N'-dicyclohexylcarboimide and 5mmol of 4 -Dimethyl...

Embodiment 2

[0091] This example provides the application of a highly selective red-absorbing heptamethine cyanine dye. The heptamethine cyanine dye synthesized in Example 1 is applied to the dark green DG0730---green camouflage coating. The dark green DG0730- --The green camouflage coating raw material composition and component mass parts are as follows:

[0092] Acrylic: 10;

[0093] The heptamethine cyanine dye: 0.25;

[0094] Flake aluminum powder: 0.5;

[0095] Pigment green: 5.0;

[0096] Pigment yellow: 4.2;

[0097] Pigment Black: 1;

[0098] Pigment red: 0.6;

[0099] Organic solvents: 6;

[0100] Other additives: 0.35 (dispersant: 0.25, defoamer: 0.1).

[0101] This embodiment also provides the above-mentioned DG0730---the preparation method of the green camouflage coating, comprising the following steps:

[0102] (1) Acrylic resin, heptamethine cyanine dye, flake aluminum powder, pigment green, pigment yellow, pigment black, pigment red, xylene, dispersant and defoamer a...

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Abstract

The invention discloses a high-selectivity red light absorption heptamethine cyanine dye and a synthetic method and an application thereof. The synthetic method comprises the steps that 2, 3, 3-trimethyl-3H-indole-5 sulfonic acid potassium salt serves as a raw material, a heptamethine cyanine dye derivative is obtained through an amidation reaction and a coupling reaction, and the heptamethine cyanine dye is obtained by reacting heptamethine cyanine dye derivative with N, N-diethyl-3-aminophenol. The dye is good in light stability, the molar extinction coefficient is 3.2*10<5>M<-1>. cm<-1>, the half-peak width is 26 nm, and the dye has good red light absorption performance and can be applied to a green camouflage coating. The color difference value between the appearance color of the prepared coating and the prepared standard color ranges from 0.5 to 1.2, the emissivity of the infrared band ranging from 3 microns to 5 microns ranges from 0.65 to 0.68, the emissivity of the infrared band ranging from 8 microns to 4 microns ranges from 0.78 to 0.79, the reflectivity of the infrared band at the 680 nm ranges from 10% to 12%, and meanwhile the coating can meet the red edge effect of green plants, the spectral channel requirement of GJB7928 and the hyperspectral requirement of GJB1411A.

Description

technical field [0001] The invention relates to the technical field of synthesis of heptamethine cyanine dyes, in particular to a highly selective red light absorption heptamethine cyanine dye and its synthesis method and application. Background technique [0002] The maximum absorption wavelength of the heptamethine cyanine dye is generally between 600 and 1000 nm, which has good fluorescence properties and a large molar absorption coefficient, and the absorption wavelength of the heptamethine cyanine dye can be adjusted by modifying the molecular structure of the heptamethine cyanine dye. To achieve the purpose of absorbing different wavelengths. Therefore, it is of great significance to explore the influencing factors of its optical-near-infrared absorption properties. [0003] Although a lot of important progress has been made in the study of heptamethine cyanine dyes, there is still a lot of work to be done in improving and perfecting the photophysical properties of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09D5/30
CPCC09B23/0075C09B23/086C09D5/30
Inventor 陶益杰张朝阳周建伟丁心雄李广德王义徐文斌
Owner 上海戎科特种装备有限公司
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