Near infrared organic photoelectric material containing cyclopentadiene selenium furan, and preparation method thereof

A cyclopentadiene and near-infrared technology, applied in organic dyes, organic chemistry, chemical instruments and methods, etc., can solve the problems of lack of synthesis methods, etc., and achieve the effects of broad application prospects, high yield, and simple structure

Inactive Publication Date: 2019-08-09
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current simple synthetic route to introduce selenium into the aromatic system to obtain heterocyclic aromatic hydrocarbons with structural diversity still has certain limitations. Cyclopentadienoselenan and its derivatives lack effect

Method used

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  • Near infrared organic photoelectric material containing cyclopentadiene selenium furan, and preparation method thereof
  • Near infrared organic photoelectric material containing cyclopentadiene selenium furan, and preparation method thereof
  • Near infrared organic photoelectric material containing cyclopentadiene selenium furan, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the preparation of compound 1

[0022]

[0023] Under nitrogen atmosphere, weigh 344mg (1.0mmol) precursor 1a and 30mg (0.01mmol) PtCl 2 , dissolved in 30mL toluene, heated to 80°C, and reacted for 3 hours. After the reaction, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 265mg of compound 1 with a yield of 77%. The lowest half-wave potential of oxidation was 0.28V. , and its electrochemical performance remained unchanged.

Embodiment 2

[0024] Embodiment 2: the preparation of compound 2

[0025]

[0026] In an argon atmosphere, 554 mg (1.0 mmol) of precursor 2a and 60 mg (0.02 mmol) of PtCl 2 (PPh 3 ) 2 Disperse in 50mL of toluene, heat to 85°C, and react for 5 hours. After the reaction, the toluene in the reaction system was removed, and the crude product was separated and purified by column chromatography to obtain 450mg of compound 2 with a yield of 81%. The lowest half-wave potential of oxidation was -0.03V, after 100 cycles of redox cyclic voltammetry scanning , and its electrochemical performance remained unchanged.

Embodiment 3

[0027] Embodiment 3: the preparation of compound 3

[0028]

[0029] Under argon protection, 876 mg (1.0 mmol) of precursor 3a and 90 mg (0.03 mmol) of platinum chloride PtCl 2 Disperse in 70mL of toluene, heat to 95°C, and react for 10 hours. After the reaction was completed, the toluene in the reaction system was removed, and the crude product was separated and purified by silica gel column chromatography to obtain 385mg of compound 3 with a yield of 44%. The lowest half-wave potential of oxidation was -0.04V, after 50 cycles of redox cyclic voltammetry scanning After that, its electrochemical performance remained unchanged.

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PUM

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Abstract

The invention belongs to the technical field of organic photoelectric material, and more specifically relates to a near infrared organic dye containing cyclopentadiene selenium furan, and a preparation method thereof. The chemical structure of the near infrared organic dye containing cyclopentadiene selenium furan is simple; the near infrared organic dye containing cyclopentadiene selenium furan is an organic photoelectric material containing cyclopentadiene selenium furan structure, possesses the properties of aromatic and nonalternant hydrocarbons at the same time, is capable of absorbing near infrared light, possesses extremely low oxidation potential and excellent electrochemical stability. The near infrared organic dye containing cyclopentadiene selenium furan is prepared through one-step intramolecular cyclisation reaction of a selenophen derivative precursor under the catalytic effect of platinum chloride. The steps are few; the yield is high; and the cost is low.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of near-infrared organic photoelectric materials containing cyclopentadienoselenan and a preparation method thereof. Background technique [0002] Functionalized PAHs have special optoelectronic properties and can be used in various organic optoelectronic devices, such as field effect transistors, photovoltaic solar cells, and light-emitting diodes, which have attracted the attention of both academia and industry. For example, pentacene, rubrene, perylene, and indolofluorene with a linear structure are all key building blocks for designing and synthesizing high-performance field-effect transistor materials. These organic semiconducting materials have the advantages of flexibility, light weight and easy shape compared with field effect transistors based on silicon or other inorganic materials. The strategies for optimizing the combination of proper...

Claims

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Application Information

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IPC IPC(8): C07D345/00C07D517/04C07D517/14C07D517/22C09B57/00
CPCC07D345/00C07D517/04C07D517/14C07D517/22C09B57/00
Inventor 周刚乔严君卢轶凡陈伟男于雪雯
Owner FUDAN UNIV
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