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摘要:
Expanded 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxaline dyes with variable substitution pattern on the peripheral thiophene ring were synthesized in moderate to very good yields by Suzuki and Buchwald-Hartwig coupling of the corresponding brominated 3-ethynyl quinoxalines. Dumbbell-shaped bis(thienyl 3-ethynyl quinoxalines) are also accessible by the Suzuki protocol. The photophysical properties were investigated by UV and fluorescence spectroscopy. Most of the obtained compounds display fluorescence in solution and some of them also in the solid state. Additionally, tuning of the emission color of the quinoxaline based chromophores can be conveniently accomplished by the remote substituent group. The determined absorption and emission maximum as well as the Stokes shifts strongly correlate with Hammett σp+ parameters. Besides, photophysical properties of selected derivatives in the solid state, biphasic solutions, and PMMA films, along with their relationships, are comparatively investigated. Moreover, two 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxaline dyes are aggregation induced emission (AIE) chromophores indicated by restriction of molecular motions. A covalently restricted 3- ethynyl quinoxaline supports that the inhibition of molecular rotation is responsible for the significant enhancement of fluorescence in acetonitrile/water mixtures.
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篇名 Synthesis and electronic properties of expanded 5-(hetero)aryl-thien-2-yl substituted 3-ethynyl quinoxalines with AIE characteristics
来源期刊 中国科学:化学(英文版) 学科
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年,卷(期) 2018,(8) 所属期刊栏目
研究方向 页码范围 909-924
页数 16页 分类号
字数 语种 英文
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中国科学:化学(英文版)
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1674-7291
11-5839/O6
16开
北京东黄城根北街16号
1950
eng
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