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

• Published in: Journal of organic chemistry Vol. 75; no. 3; pp. 856 - 863
• Main Authors: Li, Jinling, Zhang, Kai, Zhang, Xiaojie, Huang, Kuo-Wei, Chi, Chunyan, Wu, Jishan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.02.2010; Amer Chemical Soc
• Subjects: Anthracenes - chemical synthesis; Anthracenes - chemistry; Chemistry; Chemistry, Organic; Coloring Agents - chemistry; Condensed benzenic and aromatic compounds; Crystallography, X-Ray; Electrochemistry; Exact sciences and technology; General and physical chemistry; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Solubility; Spectroscopy, Near-Infrared; ACENES; GROUND-STATE; WAVELENGTHS; AGENTS; PENTACENES; DERIVATIVES; ELECTRONICS; Amphoteric; Dyes; Stability; Hydrocarbon; Solubility; Polycyclic aromatic compound; Quantum yield; Thermal stability; Near infrared radiation; Chemical reduction; Cyclic voltammetry; Near infrared spectrometry; Anions; Fluorescence yield; Pi-System; Electrochemistry; Photochemical stability; Soluble compound; Cations; Oxidation; Redox system; Chemical synthesis; Crystalline structure
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/jo902413h

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.