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A kind of tröger's base derivative, its preparation method and the test method of mechanically induced fluorescence enhancement characteristics

A derivative, fluorescence intensity technology, used in fluorescence/phosphorescence, chemical instruments and methods, organic chemistry, etc., can solve problems that have not yet been discovered

Active Publication Date: 2021-07-23
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, only a few literatures have reported The development and application of alkali AIE fluorescent materials have not been found to have AIE properties A Report on Mechanically Induced Fluorescent Chromogenic Properties of Base Derivatives

Method used

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  • A kind of tröger's base derivative, its preparation method and the test method of mechanically induced fluorescence enhancement characteristics
  • A kind of tröger's base derivative, its preparation method and the test method of mechanically induced fluorescence enhancement characteristics
  • A kind of tröger's base derivative, its preparation method and the test method of mechanically induced fluorescence enhancement characteristics

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preparation example Construction

[0043] The present invention also provides tetraphenylethylene modified tetraphenylethylene described in the above scheme The preparation method of base derivative, comprises the following steps:

[0044] Under a protective atmosphere, 4-(1,2,2-triphenylethenyl) phenylboronic acid pinacol ester, 2,8-dibromo-6H,12H-5,11-methylenediphenyl[ b,f][1,5]Diazocine, phosphate, catalyst and solvent are mixed for Suzuki coupling reaction to obtain tetraphenylethylene-modified base derivatives.

[0045] In the present invention, the protective atmosphere is preferably an inert gas, specifically high-purity nitrogen, common nitrogen or argon; the 2,8-dibromo-6H,12H-5,11-methylenediphenyl[ b, f] [1,5] diazocine and 4-(1,2,2-triphenylethenyl) phenylboronic acid pinacol ester molar ratio is preferably 1: (2 ~ 3), more Preferably it is 1:(2.3~2.5); the present invention is to the described 2,8-dibromo-6H,12H-5,11-methylene diphenyl[b,f][1,5]diazocine and There is no special requirement o...

Embodiment 1

[0070] The tetraphenylethylene modified of structure shown in formula I Synthesis of Base Derivatives 1

[0071] The synthesis steps are as follows:

[0072] Under the protection of high-purity nitrogen, 124mg of 2,8-dibromo-6H,12H-5,11-methylenediphenyl[b,f][1,5]diazocine, 300mg of 4-(1 , 2,2-triphenylvinyl)phenylboronic acid pinacol ester and 171 mg of potassium phosphate (2,8-dibromo-6H,12H-5,11-methylenediphenyl[b,f] [1,5]Diazocine, 4-(1,2,2-triphenylethenyl) phenylboronic acid pinacol ester and potassium phosphate in a molar ratio of 1:2:2.5) were mixed and dissolved in 80 mL In the mixed solvent prepared by tetrahydrofuran and 20mL of water (THF and water volume ratio are 4:1), after completely dissolving, add 5.0mg tetrakistriphenylphosphine palladium catalyst, the consumption of tetrakistriphenylphosphine palladium catalyst is 2 , 2.0% of the mass of 8-dibromo-6H,12H-5,11-methylenediphenyl[b,f][1,5]diazocine was refluxed at 100°C for 15 hours in an oil bath.

[00...

Embodiment 2

[0075] Structure shown in formula I Synthesis of base derivatives 2

[0076] The synthesis steps are as follows:

[0077] Under the protection of high-purity nitrogen, 124mg of 2,8-dibromo-6H,12H-5,11-methylenediphenyl[b,f][1,5]diazaphenocine, 450mg of 4-( 1,2,2-triphenylvinyl)phenylboronic acid pinacol ester and 171 mg of potassium phosphate (2,8-dibromo-6H,12H-5,11-methylenediphenyl[b,f] [1,5] Diazocine, 4-(1,2,2-triphenylethenyl) phenylboronic acid pinacol ester and potassium phosphate in a molar ratio of 1:3:2.5) were mixed and dissolved in 80 mL of In the mixed solvent prepared by dioxane and 20mL of water (the volume ratio of dioxane and water is 4:1), after completely dissolving, add 7.5mg of tetrakistriphenylphosphine palladium catalyst, tetrakistriphenylphosphine The amount of palladium catalyst used is 3.0% of the mass of 2,8-dibromo-6H,12H-5,11-methylenediphenyl[b,f][1,5]diazocine, under 120°C oil bath Reflux for 15 hours.

[0078] After the reaction was compl...

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Abstract

The invention relates to the technical field of organic optoelectronic functional materials, and provides an alkali derivative, a preparation method thereof, and a method for testing mechanically induced fluorescence enhancement properties. The structural formula of the tetraphenylethylene-modified base derivative provided by the present invention is shown in formula I, which has the properties of aggregation-induced luminescence and mechanically-induced fluorescence enhancement. Under the action of mechanical force, the fluorescence intensity changes obviously, and the crystal form does not change. , has good fumigation recovery characteristics and stability. The preparation method provided by the invention has simple operation and mild reaction conditions. The method for mechanically inducing fluorescence enhancement properties of tetraphenylethylene-modified base derivatives provided by the invention has simple steps, and can change the fluorescence intensity, fumigation recovery performance and crystal form changes of the tetraphenylethylene-modified base derivatives under the action of mechanical pressure. and stability testing.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric functional materials, in particular to a Base derivatives, methods for their preparation and test methods for mechanically induced fluorescence enhancement properties. Background technique [0002] Since the aggregation-induced emission (AIE) phenomenon was first discovered at the beginning of this century, a series of mechanistic explanations have been gradually proposed, including twisted intramolecular charge transfer (TICT), restricted E / Z isomerization, and photoinduced intramolecular protons. transfer (ESIPT), molecular coplanarity and J-mer formation, etc. But these theories are only applicable to explain the luminescence of a small part of AIE molecules, not the whole. Restriction of Intramolecular Rotations (RIR, Restriction of Intramolecular Rotations) and Restriction of Intramolecular Vibrations (RIV, Restriction of Intramolecular Vibrations) have a wide range of applic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/08C09K11/06G01N21/64
CPCC07D471/08C09K11/06C09K2211/1007C09K2211/1044G01N21/64G01N2021/6417
Inventor 孙景志倪珏宸蒋帅兵
Owner ZHEJIANG UNIV