Solid-state fluorescence properties and mechanofluorochromism of?D-¦Ð-A pyridinium dyes bearing various counter anions

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• 作者：Yousuke Ooyama ; ^{yooyama@hiroshima-u.ac.jp} ; Yuichiro Oda ; Yuta Hagiwara ; Hiroshi Fukuoka ; Eigo Miyazaki ; Tomonobu Mizumo ; Joji Ohshita ^{jo@hiroshima-u.ac.jp}
• 关键词：Mechanofluorochromism ; Solid-state fluorescence ; Fluorescent dyes ; Dyes/pigments ; Donor&ndash ; pi-acceptor system
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：22 July, 2013
• 年：2013
• 卷：69
• 期：29
• 页码：5818-5822
• 全文大小：1116 K

文摘

A pronounced bathochromic shift-type mechanofluorochromism (MFC) is found for D-¦Ð-A pyridinium dyes OD1-OD3 having diphenylamino group as an electron donor and pyridinium ring as an electron acceptor linked by carbazole as a ¦Ð-conjugated bridge, and bearing various counter anions (X^?=Cl^?, Br^?, or I^?). Interestingly, both absorption and fluorescence peaks of as-recrystallized dyes show bathochromic shift by grinding, and the degrees of the bathochromic shift depend on the type of counter anion of OD1-OD3. We propose that the use of various counter anions for D-¦Ð-A pyridinium dyes can be one of the most effective strategies, not only to express a pronounced MFC, but also to control changes of fluorescence properties by the grinding and heating, resulting in fine-tuning of fluorescent color change by the MFC.