New 8-substituted BODIPY-based chromophores: synthesis, optical and electrochemical properties

Heterocyclic communications

article

Nikolay Vologdin¹  Sylvain Achelle¹  Sébastien Gauthier¹  Bertrand Caro¹  Françoise Robin-le Guen¹ 

[1] Institut des Sciences Chimiques de Rennes UMR CNRS 6226

关键词: bistable redox systems;    BODIPY;    fluorescence;    Sonogashira reaction;   

DOI  :  10.1515/hc-2016-0151

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

BODIPY-based chromophores, in which an electron withdrawing difluoro-boraindacene fragment is connected via position 8 to different donor fragments, were synthesized. Their electrochemical and photophysical properties were studied. All compounds exhibit a quasi-reversible oxidation corresponding to the formation of a BODIPY π-radical cation at around 0.8 V vs. FeCp 2 + /FeCp 2 that is slightly sensitive to the nature of the electron donating group. A reversible reduction is observed around−1.6 V vs. FeCp 2 + /FeCp 2 corresponding to the formation of the BODIPY π-radical anion. Cyclic voltammetry analysis of a γ-methylenepyran substituted BODIPY indicates the formation of redox bistable system with high bistability. In dichloromethane solution, the chromophores exhibit an intense absorption band around 502 nm and an emission in the 516–528 nm range. A significant emission quench is observed in case of amino and γ-methylenepyran substituents.

【 授权许可】

CC BY|CC BY-NC-ND