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meso-Substituted Bisanthenes as Soluble and Stable Near-infrared Dyes

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journal contribution
posted on 05.02.2010, 00:00 by Jinling Li, Kai Zhang, Xiaojie Zhang, Kuo-Wei Huang, Chunyan Chi, Jishan Wu
Three meso-substituted bisanthenes, 46, were prepared in a short synthetic route from the bisanthenequinone. They exhibit largely improved stability and solubility in comparison to the parent bisanthene. All of these compounds also show near-infrared (NIR) absorption and emission with high to moderate fluorescence quantum yields. Amphoteric redox behavior was observed for 46 by cyclic voltammetry, and these compounds can be reversibly oxidized and reduced into respective cationic and anionic species by both electrochemical and chemical processes. In addition, compound 5 adopts a herringbone π-stacking motif in the single crystal.