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Intramolecular charge transfer chromophore containing triphenylamine group and its synthesis method

A triphenylamine-based, charge transfer technology, applied in chemical instruments and methods, preparation of organic compounds, luminescent materials, etc., can solve the problems of reducing fluorescence quenching concentration, poor thermal stability, large chromophore interaction, etc. The effect of increasing fluorescence quenching concentration, reducing interaction, good thermal stability and solubility

Inactive Publication Date: 2006-11-22
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the general intramolecular charge transfer chromophore has poor thermal stability, and the chromophore interaction at high concentration is relatively large, which reduces the fluorescence quenching concentration.

Method used

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  • Intramolecular charge transfer chromophore containing triphenylamine group and its synthesis method
  • Intramolecular charge transfer chromophore containing triphenylamine group and its synthesis method
  • Intramolecular charge transfer chromophore containing triphenylamine group and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 4-(Diphenylamine)benzaldehyde (0.273 g, 1.0 mmol) and 2-(3,5,5-trimethylcyclohexen-2-enylidene)malononitrile (0.186 g, 1.0 mmol) were dissolved in acetonitrile solution (20 mL). Piperidine was added dropwise as a catalyst, the mixture was refluxed for 10 hours, cooled to room temperature, the product was precipitated from the acetonitrile solution, the product was washed with deionized water, and dried to obtain pure dark red needle-like crystals, which were triphenylamine-containing The intramolecular charge transfer chromophore 4-[2-(3-dicyanomethylvinyl-5,5-dimethyl-1-cyclohexene)-ethylene]triphenylamine (BHT).

[0019] Yield: 85%

[0020] 1 H NMR (500MHz, CDCl 3 , δppm): δ1.07(s 6H, -(CH 3 ) 2 ), δ2.46(s 2H, -(CH 2 )-), δ2.59(s 2H, -(CH 2 )-), δ6.79(s 1H, -(CH)=), δ6.84-6.87(d 1H, CH=CH), δ6.99-7.02(t 3H, ArH), δ7.09-7.14( m 1H, ArH), δ7.26, 7.31(d 1H, CH=CH), δ7.29-7.30(d 3H, ArH), δ7.34-7.36(d 2H, ArH).

[0021] Elemental analysis: theoretical value C 31...

Embodiment 2

[0026] 4,4'-(anilinediyl)benzaldehyde (0.301g, 1.0mmol) and 2-(3,5,5-trimethylcyclohexen-2-enylidene)malononitrile (0.558g , 3.0mmol) was dissolved in N,N-dimethylformamide solution (20mL), piperidine, acetic acid and acetic anhydride were added dropwise as a catalyst, the mixture was refluxed for 10 hours, after cooling to room temperature, the reaction mixture was poured into water and used dichloromethane extraction. Extraction with anhydrous MgSO 4 After drying, dichloromethane was removed under reduced pressure. The initial product is purified by silica gel column chromatography with petroleum ether: dichloromethane (1:3, V / V) as the eluent, and finally obtains a deep red product with metallic luster, which is an intramolecular compound containing a triphenylamine group. The charge transfer chromophore 4,4'-bis[2-(3-dicyanomethylvinyl-5,5-dimethyl-1-cyclohexene)-ethylene]triphenylamine (BDHT).

[0027] Yield: 58%

[0028] 1 H NMR (500MHz, CDCl 3 , δppm): δ1.08(s 12H...

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Abstract

This invention discloses an intermolecular charge transfer chromogen with triphenylamine group, with a formula indicated by (1), wherein: R1 is hydrogen atom or methyl group or methoxyl group, R2 is hydrogen atom or 2-(5,5-dimethyl-3-vinylcyclohexenyl-2-enylidene)propanedinitrile group. This invention applies mild condition uses substituent group triphenylamine aldehyde or triphenylamine dialdehyde as raw material to react by heating with 2-(5,5-dimethyl-3-vinylcyclohexenyl-2-enylidene)propanedinitrile group to produce the intermolecular charge transfer chromogen with high decomposition temperature, non-coplanar structure, and triphenylamine group. By changing R1 and R2, it can obtain different absorption peak value and fluorescent emission peak, which could be used in photoluminescence, electroluminescence, data storage, light communication and bio-imaging.

Description

technical field [0001] The invention relates to an intramolecular charge transfer chromophore containing a triphenylamine group and a synthesis method thereof. Background technique [0002] Compared with inorganic materials, organic functional materials have a remarkable feature: the molecular structure can be changed through simple chemical design adjustments, thereby improving performance. Among many organic functional materials, intramolecular charge transfer materials play an extremely important role and are widely used in photoluminescence, electroluminescence, optical communication and other fields. The intramolecular charge transfer of this type of chromophore is realized by the intramolecular electron donor (D) and electron acceptor (A) transferring electrons or charges through the π-conjugated bridge, and the electron cloud distribution of the excited state and the ground state There is a large difference, so that the fluorescence emission of the compound is usuall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/42C07C253/30C09K11/06
Inventor 钱国栋陈鹭剑钟齐崔元靖杨雨王智宇邱建荣樊先平洪樟连王民权
Owner ZHEJIANG UNIV
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