A d-a-π-a type n-hybrid porphyrin-dipyrrolene nonlinear optical material and its synthesis method

A technology of nonlinear optics and optical materials, applied in the field of organic fine chemical industry, can solve the problems of inability to use for a long time, easy photobleaching, difficult to solve its difficulties, etc., and achieves high microscopic first-order hyperpolarizability and photophysical and chemical stability. good effect

Active Publication Date: 2021-07-13
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because of this, in the design and synthesis of organic nonlinear optical materials, a large number of experimental operations are required to prove that the designed molecules have better photoelectric properties, which is especially high in human resource costs, and for the device fabrication of the materials themselves, It also requires special process and equipment support, so it is difficult to solve its difficulties
At present, the photochemical stability of organic nonlinear optical materials with "D-A-π-A" structure is not good, and they are easy to photobleach during use, which makes the device life short and cannot be used for a long time

Method used

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  • A d-a-π-a type n-hybrid porphyrin-dipyrrolene nonlinear optical material and its synthesis method
  • A d-a-π-a type n-hybrid porphyrin-dipyrrolene nonlinear optical material and its synthesis method
  • A d-a-π-a type n-hybrid porphyrin-dipyrrolene nonlinear optical material and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 0.28g (0.12mmol) of 5-ethoxyformyl-2,3,3-trimethylindole and 0.61g (0.10mmol) of 5,10,15,20-tetraphenyl-N-heteroporphyrin In DMF, stirred for 5 minutes, refluxed at 150° C. for 0.5 hours, after the reaction was completed, spin-dried, filtered and purified by column chromatography to obtain a purple compound with a yield of 93%.

[0028]

Embodiment 2

[0030] Take 0.46g (0.2mmol) of 5-ethoxyformyl-2,3,3-trimethylindole and 0.61g (0.10mmol) of 5,10,15,20-tetraphenyl-N-hybrid porphyrin In DMF, stirred for 5 minutes, and refluxed at 150°C for 0.5 hours. After the reaction was completed, the purple compound was obtained by filtration and purification column chromatography with a yield of 92%.

[0031]

Embodiment 3

[0033] Take 0.23g (0.1mmol) of 5-ethoxyformyl-2,3,3-trimethylindole and 0.61g (0.10mmol) of 5,10,15,20-tetraphenyl-N-hybrid porphyrin In DMF, stirred for 5 minutes, and refluxed at 150°C for 0.5 hours. After the reaction was completed, the purple compound was obtained by filtration and purification column chromatography with a yield of 84%.

[0034]

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Abstract

The invention belongs to the technical field of organic chemical industry, in particular to the synthesis and application of a D-A-π-A type N-hybrid porphyrin-dipyrrolene nonlinear optical material. The chemical structural formula is: the synthesis method is based on 5- Formethoxy-2,3,3-trimethylindole and tetraphenyl N-hybrid porphyrin, through Knoevenagel condensation reaction, simple and high yield to obtain D-A-π-A type N-hybrid porphyrin-di Pyrrolene nonlinear optical materials. The key point is to obtain a D-A-π-A type N-hybrid porphyrin-dipyrrolene conjugated structure simply and efficiently, thereby obtaining a higher first-order hyperpolarizability, and the prepared nonlinear optical chromophore It has potential important applications in the field of optical waveguide devices.

Description

technical field [0001] The invention relates to the technical field of organic fine chemicals, in particular to the synthesis and application of a D-A-π-A type N-hybrid porphyrin-dipyrrolene nonlinear optical material. Background technique [0002] In recent years, the application of organic optoelectronic materials with excellent performance in the fields of communication, optical modulation and optical storage devices has attracted extensive attention of researchers. Among them, organic nonlinear optical chromophore materials have been widely studied because of their important role in photonic devices. and apply. Organic dyes with a "D-A-π-A" structure have great application potential in the fields of bioluminescent imaging, chemical sensors, sensitized solar cells, photoacoustic imaging, and optoelectronic materials. In general, nonlinear optical chromophores are usually composed of π-bridges, donors, and acceptors. A nonlinear optical chromophore with excellent perform...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C09K11/06
CPCC07D487/22C09K11/06C09K2211/1007C09K2211/1029
Inventor 张诺诺文柳晏佳莹刘根江刘湘郑开波李德江
Owner CHINA THREE GORGES UNIV
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