Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation
Huiquan Zuo, Qinghua Wu, Xing Guo, Zhengxin Kang, Jiangang Gao, Ying Wei, Changjiang Yu, Lijuan Jiao, Erhong Hao
Abstract
promoted oxidative nucleophilic hydrogen substitution, site-selective direct and stepwise cyanation of BODIPYs using tetrabutylammonium cyanide was developed to give α-cyanated BODIPY derivatives. Characterization of optical and electrochemical properties of these dyes provides substantial enhancement of the electron affinity, with a reduction potential and LUMO level as low as -0.04 V and -4.43 eV, respectively. Radical anions of these electron-deficient 3,5-dicyanated BODIPYs were characterized by absorption and EPR spectroscopy.
Topics & Concepts
ChemistryCyanationHOMO/LUMOPhotochemistryRedoxCyanideElectrochemistryInorganic chemistryOrganic chemistryMoleculeCatalysisElectrodePhysical chemistryLuminescence and Fluorescent MaterialsOrganic Light-Emitting Diodes ResearchConducting polymers and applications