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Visible light responsive donor-acceptor stenhouse adducts with indoline-tri/tetra-phenylethylene chromophore: Synthesis, aggregation-induced emission, photochromism and solvent dependence effect
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-03-14 , DOI: 10.1016/j.dyepig.2020.108352
Qinghua Yan , Chengpeng Li , Sheng Wang , Ziwei Lin , Qing Yan , Derong Cao

We designed and synthesized two new visible light triggered photochromic and aggregation-induced emission compound derived from the third generation donor−acceptor Stenhouse adducts (DASAs) with indoline-tri/tetra-phenylethylene moiety (abbreviation: SPE-IF/TPE-IF). The chemical structures of these compounds are identified by NMR, MS and so on. The key intermediate SPE-ID/TPE-ID as donor showed excellent AIE properties in water-THF (v/v) solutions. The absorption and emission of SPE-IF/TPE-IF were investigated by UV–Vis and fluorescence spectroscopy, respectively. The results shown they exhibited photochromic with fatigue resistance and fluorescent switching properties with visible light regulation. The open/colored triene and closed/colorless cyclopentenone isomers of SPE-IF/TPE-IF were equipped with high photo bleaching and fluorescence effect upon alternating visible light irradiation and heating both in solution and in PMMA doped solid state. And the solvent dependence effect of TPE-IF was studied. The photochromic mechanism of SPE-IF/TPE-IF was also basically investigated by computational method. These results indicate SPE-IF or TPE-IF is a promising candidate for visible light-responsive smart materials.



中文翻译:

可见光响应的供体-受体模板加合物与二氢吲哚三/四苯基乙烯发色团:合成,聚集诱导的发射,光致变色和溶剂依赖性效应

我们设计并合成了两种新的可见光触发的光致变色和聚集诱导的发射化合物,它们是由具有吲哚三-三/四苯基乙烯部分(缩写:SPE-IF / TPE-IF)的第三代供体-受体Stenhouse加合物(DASA)衍生的。这些化合物的化学结构通过NMR,MS等鉴定。作为供体的关键中间体SPE-ID / TPE-ID在水-THF(v / v)溶液中显示出出色的AIE性能。SPE-IF / TPE-IF的吸收和发射分别通过紫外可见光谱和荧光光谱进行了研究。结果表明,它们表现出具有耐疲劳性的光致变色和具有可见光调节的荧光开关特性。SPE-IF / TPE-IF的开环/有色三烯和闭环/无色环戊烯酮异构体在溶液和PMMA掺杂固态交替可见光照射和加热时均具有高光漂白和荧光效果。并研究了TPE-IF对溶剂的依赖性。还通过计算方法基本研究了SPE-IF / TPE-IF的光致变色机理。这些结果表明SPE-IFTPE-IF 是可见光响应智能材料的有希望的候选人。

更新日期:2020-03-16
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