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

Jinling Li, Kai Zhang, Xiaojie Zhang, Kuo-Wei Huang, Chunyan Chi, Jishan Wu

Research output: Contribution to journalArticlepeer-review

66 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)856-863
Number of pages8
JournalThe Journal of Organic Chemistry
Volume75
Issue number3
DOIs
StatePublished - Feb 5 2010

ASJC Scopus subject areas

  • Organic Chemistry

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