Benzothiazole derivatives with aggregation-induced luminescent properties containing triphenylethylene or tetraphenylethylene structure, preparation method and application thereof

Abstract

The invention discloses a benzothiazole derivative containing a triphenylethylene or tetraphenylethylene structure and having aggregation-induced emission property and a preparation method and application thereof. The preparation method comprises the following steps: with 2-amino-6-methoxybenzothiazole as a start raw material, performing a ring-opening reaction under an alkaline condition to generate 2-amino-5-methoxythiophenol; performing a ring-closing reaction with an aromatic aldehyde compound containing a triphenylethylene or tetraphenylethylene structure to obtain a methoxy-containing benzothiazole derivative, or performing demethylation to obtain a hydroxyl-containing benzothiazole derivative, wherein the compound also can be modified through a group substitution reaction to generate a benzothiazole derivative containing other functional groups. The benzothiazole derivative disclosed by the invention has relatively low luminous intensity in a solution, emits strong fluorescence in an aggregation state or solid state, and belongs to good aggregation-induced emission materials; the synthesis is relatively simple, and the cost of the raw materials is low, so that large-scale commercial production is easy to realize; the benzothiazole derivative plays an important role in the fields of electroluminescent devices, fluorescent probes, fluorescent switches, organism imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a class of benzothiazole derivatives with triphenylethylene or tetraphenylethylene structures and aggregation-induced luminescent materials, as well as their preparation methods and applications. Background technique [0002] Benzothiazole and its derivatives are widely found in nature. The luciferin extracted from fireflies contains a benzothiazole structure, and benzothiazole derivatives can be isolated and identified from corn coleoptiles, and the derivatives have plant growth inhibitory functions. Crude oils formed from lake swamps have a high content of benzothiazoles. Benzothiazole and its derivatives can be widely used in organic light-emitting diodes (OLED), biomedicine, metal ion detection and industrial production. [0003] However, when traditional benzothiazole derivatives are in a high concentration or in a solid state, the molecul...

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Problems solved by technology

[0005] However, so far, the benzothiazole derivatives with luminescent properties developed are relatively limited. Many of these compounds are still slightly modified on the traditional structure, and there is a certain gap in luminous efficiency compared with AIE materials. Styrene and tetraphenylethylene structures not only have obvious aggregation-induced luminescent properties, but also have high thermal stability and luminous intensity, and are used in the preparation of organic electroluminescent devices and other luminescent materials (Chi Zhenguo, Xu Bingjia, Li Xiaofang, etc., Synthesis method and application of aggregation-induced luminescence materials containing both triphenylethylene and tetraphenylethylene structures, Chinese patent 201010219154.1)

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