meso-Substituted bisanthenes as soluble and stable near-infrared dyes.
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.
Li
Jinling
J
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Zhang
Kai
K
Zhang
Xiaojie
X
Huang
Kuo-Wei
KW
Chi
Chunyan
C
Wu
Jishan
J
D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry; D004396:Coloring Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D012995:Solubility; D019265:Spectroscopy, Near-Infrared
D000873:Anthracenes; D004396:Coloring Agents; C031404:bisantrene