Methyl pyridinium with organic two-photon absorption materia, and preparation method and application thereof

A technology of two-photon absorption and picoline salt, which is applied in the fields of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, and can solve rare problems

Inactive Publication Date: 2012-10-03
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are relatively few reports on the use of organic pyridinium salts for

Method used

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  • Methyl pyridinium with organic two-photon absorption materia, and preparation method and application thereof
  • Methyl pyridinium with organic two-photon absorption materia, and preparation method and application thereof
  • Methyl pyridinium with organic two-photon absorption materia, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: Preparation of N-methyl-(E)-4-[4'-(dianilino styryl)]pyridine-2,6-dicarboxylic acid dimethyl trifluoromethanesulfonate

[0091] (1) Preparation of pyridine-2,6-dicarboxylic acid

[0092]

[0093] Add 350 mL of distilled water, 41.0 g (261 mmol) of potassium permanganate and 5.0 g (46 mmol) of 2,6-lutidine into a 500 mL round bottom flask. Boiling and reflux reaction for 3 hours. Cool and filter, concentrate under reduced pressure to one-fifth of the original volume, and add 10mL of 70% sulfuric acid while hot. Cool naturally and filter to obtain crude product. Recrystallized twice from water to obtain 7.3 g of white solid. Yield: 98.6%. Mp: 229-230°C.

[0094] (2) Preparation of dimethyl pyridine-2,6-dicarboxylate

[0095]

[0096] Add 31.0g (190mmol) pyridine-2,6-dicarboxylic acid into a 500mL round bottom flask, coat the lower end of the spherical condenser tube with vacuum silicone ester, insert the spherical condenser tube, and pour 120mL (165...

Embodiment 2

[0112] Example 2: 4-(N-methyl-2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)-4'-(2,6-dimethoxycarbonyl-pyridine- Preparation of 4-(E)-vinyl)triphenylamine trifluoromethanesulfonate

[0113] (1) The preparation method of 4-methylenetriphenylphosphoryl-pyridine-2,6-dicarboxylate is the same as in Example 1.

[0114] (2) Preparation of 4,4'-bis(2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)triphenylamine

[0115]

[0116] Add 242.8mg (0.48mmol) chloride-4-methylenetriphenylphosphoryl-pyridine-2,6-dicarboxylic acid dimethyl ester, 60.3mg (0.20mmol) bis(4-methyl) into a 50mL round bottom flask Acylphenyl) aniline, nitrogen protection. Inject 20.0 mL of absolute methanol with a 20.0 mL syringe. Cool in an ice-water bath and stir at medium speed. Use a 5.0mL syringe to slowly inject 5.0mL (123.60mmol) of an absolute methanol solution containing 21.61mg (0.40mmol) of sodium methoxide into the flask. After the dropwise addition, the ice-water bath was removed, and the stirring reacti...

Embodiment 3

[0120] Example 3: Preparation of 4,4'-bis(N-methyl-2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)triphenylamine bis-trifluoromethanesulfonate

[0121] (1) The preparation method of 4,4'-bis(2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)triphenylamine is the same as in Example 2.

[0122] (2) Preparation of 4,4'-bis(N-methyl-2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)triphenylamine bis-trifluoromethanesulfonate

[0123]

[0124] Add 136.6mg (0.2mmol) 4,4'-bis(2,6-dimethoxycarbonyl-pyridine-4-(E)-vinyl)triphenylamine into a 50mL round-bottomed flask, and protect it with nitrogen. Inject 8.0 mL of dichloromethane with a 10.0 mL syringe. Under an ice-water bath, use a 1.0mL syringe to inject a dichloromethane solution containing 0.04mL methyl trifluoromethanesulfonate 1.0mL (0.5mmol). Stir at medium speed for 72 hours at 40°C. The reaction was cooled to room temperature, diluted with 50 mL of anhydrous ether, and cooled overnight in a refrigerator. Suction filtration, discard the...

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Abstract

The invention relates to the field of organic nonlinear optical materials and relates to methyl pyridinium with an organic two-photon absorption material, and a preparation method and the application of the methyl pyridinium. The structural formula of the product is described in structural formula (I); the preparation method comprises the steps of taking 2,6-dimethyl pyridine as a raw material and finally obtaining a compound (I) by conducting oxidizing reaction, esterification reaction, methylolation reaction, halogenation reaction, nucleophilic addition reaction, Wittig reaction and the final methylation reaction. The raw materials are easy to access, and the synthesis steps are simple. The compound (I) has excellent two-photon absorption performance and good water solubility and is an ideal biological fluorescence probe; an obvious solvatochromism phenomenon easily occurs, the compound can be used for detecting water content in a common organic solvent, can also be used as a fluorescent probe for detecting the PH value in a solution system, has a series of advantages of high sensibility, quick response, identification by naked eyes and the like, and has an excellent application prospect.

Description

technical field [0001] The invention relates to the field of organic nonlinear optical materials, in particular to a picoline salt of an organic two-photon absorption material containing dimethyl pyridine-2,6-dicarboxylate groups, a preparation method and application thereof. Background technique [0002] The application of two-photon absorption technology in the fields of high-density data storage, optical stability and limiting, two-photon up-conversion laser, three-dimensional microfabrication, and biological cell fluorescence imaging has become the most attractive and most promising field in optics and its interdisciplinary fields. one of the active areas of research. Compared with inorganic two-photon absorbing materials, organic two-photon absorbing materials have high nonlinear optical coefficient, low cost, easy device fabrication and integration, performance can be adjusted through structural modification, high optical damage threshold, fast nonlinear optical respon...

Claims

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Application Information

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IPC IPC(8): C07D213/79C09K9/02G01N21/78G01N21/80
Inventor 肖海波梅翀张晓瑛
Owner SHANGHAI NORMAL UNIVERSITY
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