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基于噻吩[3.4-c]吡咯-4,6-二酮的给体-受体-给体型 AIE 化合物:合成、电化学聚合及电致变色。

Donor-acceptor-donor type AIEgens based on thieno[3.4-c]pyrrole-4,6-dione: Synthesis, electropolymerization, and electrochromism.

机构信息

Guangxi Key Laboratory of Electrochemical and Magneto-chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin, China.

Department of Civil Engineering, Qingdao University of Technology, Linyi, China.

出版信息

Luminescence. 2024 Aug;39(8):e4843. doi: 10.1002/bio.4843.

DOI:10.1002/bio.4843
PMID:39129388
Abstract

Photoelectric functional materials with electrochemical reversible activity and fluorescence intensities have attracted significant interest due to their wide range of applications in optoelectronic devices. In this work, a series of photoresponsive and electroactive monomers based on thieno[3.4-c]pyrrole-4,6-dione (TPD) are synthesized and characterized. They possess planar geometry with smaller dihedral angles owing to the existence of a noncovalent conformation lock coming from the S atoms and the O atoms. Crystallographic, spectroscopic, and computational results reveal that the introduction of the TPD unit can endow the monomers with aggregation-induced emission (AIE), reduced energy levels, and increased electrochemical activity. The monomers were successfully polymerized through the electrochemical method, and the corresponding polymers displayed reversible electrochemical activity and stability. Moreover, polymer films based on 3,3-dimethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine (ProE)-TPD have electrochromic properties in the near-infrared field with a high value of optical contrast ratio (∆T) of 27.1% at 1000 nm.

摘要

光电功能材料具有电化学可逆活性和荧光强度,由于它们在光电器件中的广泛应用而引起了极大的兴趣。在这项工作中,合成并表征了一系列基于噻吩并[3.4-c]吡咯-4,6-二酮(TPD)的光响应和电活性单体。它们具有平面几何形状,由于 S 原子和 O 原子的存在,存在非共价构象锁定,因此二面角较小。晶体学、光谱学和计算结果表明,引入 TPD 单元可以赋予单体聚集诱导发射(AIE)、降低能级和增加电化学活性。通过电化学方法成功聚合了单体,所得聚合物表现出可逆的电化学活性和稳定性。此外,基于 3,3-二甲基-3,4-二氢-2H-噻吩并[3,4-b][1,4]二恶烷(ProE)-TPD 的聚合物薄膜在近红外场具有电致变色性能,在 1000nm 处光学对比度(∆T)高达 27.1%。

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