D-pi-A dipyrro fluorescent dye and synthesis method thereof

A technology of dipolypyrrole and compound, which is applied in the directions of organic dyes, luminescent materials, chemical instruments and methods, etc., can solve the problems of difficult expansion of substrates, long reaction time, complicated reaction process, etc., and achieves easy control and saving of synthetic reaction conditions. Production time, the effect of simplifying the reaction process

Active Publication Date: 2017-12-22
宜昌市蓝天彩印股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The reaction process is more complicated, the reagents and reaction conditions used are more harsh, and the production cost is higher
[0012] It can be seen that the above-mentioned methods generally have some disadvantages: long reaction time, harsh conditions, low yield, and difficult expansion of the substrate

Method used

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  • D-pi-A dipyrro fluorescent dye and synthesis method thereof
  • D-pi-A dipyrro fluorescent dye and synthesis method thereof
  • D-pi-A dipyrro fluorescent dye and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Take 2,3,3-trimethyl-6-methoxyindole 1 (1.89g, 9.00mmol), weigh 2-formylpyrrole (1.72g, 18.00mmol), measure 0.15L of toluene solution, and take 0.24 mL of glacial acetic acid and 0.30 mL of piperidine were mixed, heated and stirred, refluxed at 120°C for 2 hours, spin-dried and purified by filtration to obtain yellow compound 3 (949.60 mg), yield: 31%.

[0037]

Embodiment 2

[0039] Take 2,3,3-trimethyl-6-methoxyindole 1 (18.00mmol), weigh 2-formylpyrrole (18.00mmol), measure 0.15L of toluene solution, take 0.24mL of glacial acetic acid, piper 0.30 mL of pyridine was mixed, heated and stirred, refluxed at 120° C. for 2 hours, spin-dried and purified by filtration to obtain yellow compound 3 (919.60 mg), yield: 35%.

[0040]

Embodiment 3

[0042] Take 2,3,3-trimethyl-6-methoxyindole 1 (9.00mmol), weigh 2-formylpyrrole (36.00mmol), measure 0.15L of toluene solution, take 0.24mL of glacial acetic acid, piper 0.30 mL of pyridine was mixed, heated and stirred, refluxed at 120°C for 2 hours, spin-dried and purified by filtration to obtain yellow compound 3 (900.60 mg), yield: 42%:

[0043]

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PUM

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Abstract

The invention discloses a vinyl bridged bipolypyrrole compound containing an electron donor, pi and an electron acceptor simultaneously (D-pi-A) and a synthesis method of the compound. The structure of the compound is shown as the formula in the description, wherein a substituent group R1 is an electron-donating group such as an alkoxy group, an amino group, a hydroxyl group and the like, and R2 is an electron-withdrawing group such as an acyl group, an aldehyde group, a carboxyl group, an acylamino group, a sulfonic group, a cyano group, a nitro group, a haloform group, a quaternary amine group and the like. The D-pi-A vinyl bridged bipolypyrrole compound is generated finally from a 2,3,3-trimethylindole derivative and a pyrrole-2-carboxaldehyde derivative as raw materials through a Knoevenagel condensation reaction under the action of an organic catalyst. The synthesis method of the compound containing the electron donor, pi and the electron acceptor (D-pi-A) is simple, reaction conditions are easy to control, and the method has universal adaptability. Pi conjugation, band gap and photoelectric property of the material can be regulated and controlled effectively by selecting proper fluorophore, electron donor and electron acceptor.

Description

technical field [0001] The invention discloses a vinyl bridged dipyrrole compound containing an electron donor-π-electron acceptor (D-π-A type) and a synthesis method thereof, and the compound intermediate can be widely used in Environmental, analytical, materials science and other fields. Background technique [0002] In a wide range of organic π systems, electron donor-π-electron acceptor (D-π-A) type organic compounds have various excellent optoelectronic properties due to their low energy bandgap, and have attracted more and more attention in recent years. big interest. Another attractive advantage of this type of material is that its π-conjugation, energy bandgap, and optoelectronic properties can be effectively tuned by selecting appropriate fluorophores, electron donors, and electron acceptors. So far, dyes of D-π-A type have been developed and applied in various fields. The existing synthetic vinyl bridged compounds generally have the following methods: [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C07D487/14C09K11/06C09B23/10
CPCC07D403/06C07D487/14C09B23/0091C09B23/105C09K11/06C09K2211/1029
Inventor 晏佳莹李玉姣张诺诺肖倩倩吕薇雅孔帅李德江
Owner 宜昌市蓝天彩印股份有限公司
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