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V-shaped conjugated light-absorbing organic salt compound and its use

A technology of organic salts and conjugated light, which is applied in the fields of organic polymer chemistry and material chemistry, can solve the problems that no V-type conjugated organic salt compounds have been reported, affect the macro-scale nonlinear optical response, and are difficult

Inactive Publication Date: 2007-01-03
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these one-dimensional compounds have obvious problems in terms of nonlinear optical properties: one is that it is difficult to solve the transparency-efficiency balance with traditional D / A systems, because increasing conjugation length is usually accompanied by electronic transition states The second is that the vast majority of molecules that push / pull electrons in one dimension tend to be center-symmetrically arranged in the crystal and appear to be non-SHG active; the third is the problem of phase matching, for crystals with high symmetry , the effective nonlinear phase matching is very small and also affects the macroscale nonlinear optical response
In terms of photosensitizers and initiators for two-photon polymerization, there are no reports of V-type conjugated organic salt compounds

Method used

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  • V-shaped conjugated light-absorbing organic salt compound and its use
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  • V-shaped conjugated light-absorbing organic salt compound and its use

Examples

Experimental program
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Effect test

Embodiment 1

[0084] Synthesis of 3,6-bis[2-(N-methylpyridinium-4-ylvinyl)]-N-pentyl-9hydrocarbazole-di-p-toluenesulfonate:

[0085] The first step: the synthesis of 1,4-dimethylpyridinium p-toluenesulfonate:

[0086] Add 150mL of ethanol, 4.7g (50mmol) of 4-methylpyridine and 9.3g (50mmol) of methyl p-toluenesulfonate to the reaction vessel, heat and reflux for 6 hours, cool, evaporate most of the dissolved matter, and cool in an ice-water bath , filtered and dried to obtain 14.0 g of white crystals with a yield of 93%.

[0087] The second step: the synthesis of N-pentyl-9-hydrocarbazole-3,6-dialdehyde:

[0088] DMF 2.35mL (0.03mol) was placed in a three-necked flask, and cooled to below 10°C with a water bath. POCl 3 2.80 mL (0.03 mol) was slowly added dropwise into DMF using a constant pressure dropping funnel, and the temperature was controlled below 10°C. Dissolve 0.715 g (0.003 mol) of N-pentylcarbazole in dichloroethane, pour it into the reaction system, and raise the temperature...

Embodiment 2

[0092] Synthesis of 3,6-bis[2-(N-(thiazole-3-methyl)-pyridinium-4-ylvinyl)]-N-methyl-9-hydrocarbazole-dibromide:

[0093]The first step: the synthesis of 3,6-bis[2-(pyridin-4-yl)-vinyl]-N-methyl-9-hydrocarbazole

[0094] 1.625 g (5 mmol) of 3,6-dibromo-N-methyl-9-hydrocarbazole, 15.5 mg (0.06 mmol) of palladium acetate, and 150 mg (0.5 mmol) of tris(o-tolyl)phosphine were added to the reaction vessel. 2.10 g (20 mmol) of 4-vinylpyridine and 20 mL of triethylamine were refluxed for 24 hours under nitrogen protection, filtered after cooling, and the obtained solid was washed three times with water, then dissolved in THF, dried, filtered, and evaporated to remove the solvent. 1.10 g of orange solid was obtained with a yield of 59%.

[0095] The second step: 3,6-bis[2-(N-(thiazol-3-methyl)-pyridinium-4-ylvinyl)]-N-methyl-9-hydrocarbazole-dibromide Synthesis

[0096] Add ethanol 150mL, 3,6-bis[2-(pyridin-4-yl)-vinyl]-N-methyl-9-hydrocarbazole 3.87g (10mmol) and 3-bromomethylthia...

Embodiment 3

[0098] 3,6-bis[2-(N-(2,4-dinitrophenyl)-pyridinium-4-ylvinyl)]-N-methyl-9-hydrocarbazole-diiodide salt synthesis:

[0099] Add 50 mL of ethanol, 3,6-bis[2-(pyridin-4-yl)-vinyl]-N-methyl-9-hydrocarbazole 0.187 g (1 mmol) and 2,4-dinitrate into the reaction vessel 0.356 g (2 mmol) of iodobenzene was heated to reflux for 40 hours, cooled, and most of the solvent was evaporated, cooled in an ice-water bath, filtered, and dried to obtain 0.152 g of a dark red powder with a yield of 28%.

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Abstract

The present invention belongs to the field of organic polymer chemistry and material chemistry, and is especially V-shaped conjugated light-absorbing organic salt compound and its use. The V-shaped conjugated light-absorbing organic salt compound is prepared with corresponding organic salt and heterocyclic dialdehyde, and through condensation or reaction with halogenated compound in V-shaped conjugation system. It has the structure as shown. The V-shaped conjugated light-absorbing organic salt compound may be as photsensitizer and / or initiator for single or double photon polymerization, as single or double photon bioluminescence probe with microM level use concentration, and as second order non-linear optical material; and its crystal may be used as electro-optical material and tera Hz beat frequency generator.

Description

technical field [0001] The invention belongs to the fields of organic macromolecule chemistry and material chemistry, and in particular relates to V-type conjugated light-absorbing organic salt compounds and applications thereof. Background technique [0002] With the vigorous development of the information industry, higher requirements are put forward for high-speed optical communication, optical information storage, optoelectronics and other fields. Nonlinear optical materials have important applications in optical signal processing, optical switching, frequency conversion (frequency doubling, difference frequency, mixing, optical parametric oscillation), optical data storage, optical communication, etc. Because of the characteristics of large nonlinear optical coefficient, small dielectric constant, fast response speed, high damage threshold, and easy molecular design and optimization, organic nonlinear optical materials have attracted much attention for their potential a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06C07D409/14C08K5/3432G02F1/355C07D213/36C07D209/86
Inventor 段宣明陈卫强谷杰董贤子
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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