College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, Zhejiang, P. R. China.
College of Pharmacy and Department of Medical Oncology, The Affiliated Hospital of Hangzhou Normal University, School of Medicine, Hangzhou Normal University, Hangzhou 311121, Zhejiang, P. R. China.
J Org Chem. 2023 May 5;88(9):5291-5299. doi: 10.1021/acs.joc.2c02604. Epub 2023 Apr 20.
Fusion selenophene endows the chromophore with more intrinsic and special functions. Herein, nonsymmetric selenophene-fused BODIPYs were designed and synthesized starting from the selenophene unit. The fused ring of selenophene not only maintains the rigid structure of BODIPY but also further modulates its spectral properties. The newly prepared dyes possessed many promising properties including large molar extinction coefficients, low fluorescence quantum yields, and moderate singlet oxygen generation. Quantum calculations affirmed that the smaller singlet-triplet energy gap and larger spin-orbit coupling cause efficient intersystem crossing, thus enhancing the singlet oxygen generation yield. Furthermore, selenophene-fused BODIPY exhibited significant phototoxicity with negligible dark cytotoxicity, based on the fluorescence imaging of the reactive oxygen species detection experiment.
硒吩赋予生色团更多内在和特殊的功能。本文从硒吩单元出发，设计并合成了非对称硒吩稠合的 BODIPY。硒吩的稠合环不仅保持了 BODIPY 的刚性结构，而且进一步调节了其光谱性质。新合成的染料具有许多有前途的性质，包括大摩尔消光系数、低荧光量子产率和适度的单线态氧生成。量子计算证实，较小的单重态-三重态能量差和较大的自旋轨道耦合导致有效的系间窜跃，从而提高了单线态氧生成产率。此外，基于活性氧物种检测实验的荧光成像，硒吩稠合 BODIPY 表现出显著的光毒性，而暗毒性可忽略不计。
