Campbell Jacob W, Tung Matthew T, Robertson Katherine N, Beharry Andrew A, Thompson Alison
Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, Nova Scotia B3H 4J3, Canada.
Department of Chemistry and Physical Sciences, University of Toronto, Mississauga, Ontario L5L 1C6, Canada.
J Org Chem. 2023 Aug 4;88(15):10655-10661. doi: 10.1021/acs.joc.3c00708. Epub 2023 Jul 13.
Reported herein are the synthesis and characterization of BODIPYs bearing heterocycles at boron. To synthesize this series, various chalcogenophenes (furan, thiophene, selenophene, and tellurophene) were lithiated and then used as nucleophiles to attack the boron center of a parent -BODIPY. Compounds in the series were compared with respect to their photophysical and structural properties, and trends were discussed. By virtue of the "heavy atom effect", as the mass of the heterocycle appended to the BODIPY core increases, compounds exhibit a higher singlet oxygen quantum yield. The BODIPY with tellurophene at boron exhibits the highest quantum yield (Φ = 0.68) in the series and reduced emission (Φ = 0.01).
本文报道了在硼原子上带有杂环的氟硼二吡咯（BODIPY）的合成与表征。为了合成该系列化合物，将各种硫属元素苯（呋喃、噻吩、硒吩和碲吩）进行锂化，然后用作亲核试剂进攻母体BODIPY的硼中心。对该系列化合物的光物理和结构性质进行了比较，并讨论了其变化趋势。由于“重原子效应”，随着连接到BODIPY核心的杂环质量增加，化合物表现出更高的单线态氧量子产率。硼原子上带有碲吩的BODIPY在该系列中表现出最高的量子产率（Φ = 0.68）和较低的发射率（Φ = 0.01）。
