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J Org Chem. 2010 Feb 5;75(3):856-63. doi: 10.1021/jo902413h.

meso-Substituted bisanthenes as soluble and stable near-infrared dyes.

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1
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.

Abstract

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 pi-stacking motif in the single crystal.

PMID:
20055372
DOI:
10.1021/jo902413h
[Indexed for MEDLINE]
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