meso-Substituted bisanthenes as soluble and stable near-infrared dyes
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
KAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
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Abstract(Chemical Equation Presented) Three meso-substituted bisanthenes, 4-6, 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 4-6 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. © 2010 American Chemical Society.
SponsorsThis work was financially supported by the NRF Competitive Research Program (R-143-000-360281) and NUS Young Investigator Award (R-143-000-356101).
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry
Is Supplemented ByLi, J., Zhang, K., Zhang, X., Huang, K.-W., Chi, C., & Wu, J. (2011). CCDC 812853: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw8v21
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