Synthesis and Optical Properties of Imidazole- and Benzimidazole-Based Fused 蟺-Conjugated Compounds: Influence of Substituent, Counteranion, and 蟺-Conjugated System

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• 作者：Koji Takagi ; Kazuma Kusafuka ; Yohei Ito ; Koji Yamauchi ; Kaede Ito ; Ryoichi Fukuda ; Masahiro Ehara
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：July 17, 2015
• 年：2015
• 卷：80
• 期：14
• 页码：7172-7183
• 全文大小：608K
• ISSN：1520-6904

文摘

Fused 蟺-conjugated imidazolium chlorides having hydrogen (1-Cl), octyloxy (2-Cl), N,N-dibutylamino (3-Cl), trifluoromethyl (4-Cl), and cyano (5-Cl) groups substituted on the benzene ring at the 2-position of imidazole were prepared. Counteranion exchanges from chloride to bis(trifluoromethanesulfonyl)imidate (2-TFSI) and tetrafluoroborate (2-BF4) were performed. The optical properties of these compounds (absorption and emission wavelengths, fluorescence quantum yield, and solvatochromism) were influenced by both the substituent and anion character, which was investigated by theoretical calculations using the density functional theory (DFT) and symmetry-adapted cluster鈥揷onfiguration interaction (SAC鈥揅I) methods. Fused 蟺-conjugated benzimidazolium chlorides having N,N-dibutylamino (6-Cl) and cyano (7-Cl) groups were also prepared to observe the different solvatochromic shifts.