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New organic compound with AIE (aggregation-induced emission) effects and synthesis method thereof

A technology for organic compounds and synthesis methods, applied in the field of organic synthesis, can solve the problems of difficult molecular design, low glass transition temperature, limited compounds, etc., and achieves the effects of high popularization and application value, simple synthesis process, and easy availability of raw materials

Inactive Publication Date: 2014-04-09
HUAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, the developed compounds with AIE effect are still very limited, many of these compounds are based on silole derivatives
Throughout the reported literature, silole derivatives have obvious disadvantages: low glass transition temperature and difficult molecular design

Method used

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  • New organic compound with AIE (aggregation-induced emission) effects and synthesis method thereof
  • New organic compound with AIE (aggregation-induced emission) effects and synthesis method thereof
  • New organic compound with AIE (aggregation-induced emission) effects and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A kind of novel organic compound with AIE effect of the present embodiment, the structural formula of this organic compound is:

[0038]

[0039] The NMR (nuclear magnetic resonance), MS (mass spectrum) parameters of the organic compound are as follows:

[0040] 1 H NMR (DMSO-d 6 , 400MHz, ppm) δ: 5.57(s, 2H), 6.63(d, J=8.4Hz, 4H), 6.96(d, J=8.4Hz, 2H), 7.10-7.16(m, 6H), 7.35-7.40 (m, 6H), 7.57(s, 1H), 7.76(d, J=8.4Hz, 2H);

[0041] 13 C NMR (DMSO-d 6 , 100MHz, ppm) δ: 107.71, 113.90, 118.78, 120.84, 121.25, 124.15, 125.09, 126.45, 127.40, 129.73, 129.95, 136.21, 146.31, 148.35, 149.67;

[0042] MS(EI)(m / z): calcd for C 27 h 21 N 3 , 387.17; found 388.17([M+H] + ).

[0043] A new type of organic compound with AIE effect in this embodiment can overcome the shortcomings of existing Silole and other common compounds with AIE properties, has good thermal stability and excellent luminescent performance, and can be used in organic electroluminescent devices and Th...

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Abstract

The invention discloses a new organic compound with AIE effects (aggregation-induced emission), and belongs to the technical field of organic synthesis. The structural formula of the organic compound is shown in the specification, a synthesis method thereof comprised the following steps: (1) under ice bath conditions, adding a POCl3 solution while stirring to refined DMF (dimethyl formamide); heating up to 55 DEG C, adding triphenylamine to obtain a compound 1; (2) dissolving the compound 1 obtained by the step (1) in a mixed solution of 4-nitrophenyl acetonitrile and anhydrous ethanol, heating for refluxing for 2h, adding piperidine, continuing refluxing for reaction for 2h, and obtaining a compound 2 by vacuum drying; (3) dissolving the compound 2 obtained by the step (2) in a mixed solution of stannous chloride and the anhydrous ethanol, heating for refluxing for reaction for 0.5h, and obtaining the new organic compound with the AIE effects by vacuum drying. The new organic compound with the AIE effects had good thermal stability and excellent luminescent properties, and can be used for preparation of organic electroluminescent devices and organic fluorescent dyes.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, and more specifically relates to an organic fluorescent material with aggregation-induced emission (AIE) and a synthesis method thereof. Background technique [0002] Half a century ago, Forster and Kasper found that the fluorescence intensity of the compound pyrene decreased with the increase of the concentration in the solution, and soon researchers found that this phenomenon existed in most aromatic compounds. This phenomenon is due to the π-π stacking formed by the intermolecular interactions, and the interaction between the planar conjugated chromophores becomes stronger, forming excimerates that lead to fluorescence quenching. Traditional fluorescent chromophores emit strong light in dilute solutions, but in practical applications, fluorescent materials need to be made into solid or thin films, which inevitably leads to the problem of aggregation between fluorescent molecules. In...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/42C07C253/30C09K11/06H01L51/54
Inventor 刘道富任军杨家祥
Owner HUAINAN NORMAL UNIV
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