Regioselective Synthesis of Directly Connected BODIPY Dimers through Oxidative Coupling of α-Amino-Substituted BODIPYs
Long Wang, Qinghua Wu, Zhengxin Kang, Xing Guo, Wei Miao, Zhongxin Li, Huiquan Zuo, Hua Wang, Hongwei Si, Lijuan Jiao, Erhong Hao
Abstract
A family of directly β,β-linked BODIPY dimers with amino groups at α-positions were regioselectively prepared by the oxidative coupling reaction of α-amino-substituted BODIPYs. The structure of one representative dimer was elucidated by X-ray diffraction analysis, showing its twisted orientation of two BODIPY units with a dihedral angle of 49°. Comparing with the corresponding monomers, these dimers showed red-shifted absorptions and emissions along with efficient intersystem crossing, giving Φ Δ of 43% for dimer 4b in toluene, indicating potential use as heavy-atom-free photosensitizers.
Topics & Concepts
BODIPYChemistryDimerDihedral angleRegioselectivityIntersystem crossingMonomerTolueneOxidative phosphorylationPhotochemistryOxidative coupling of methaneStructural isomerStereochemistryCrystallographyMoleculeOrganic chemistryExcited stateFluorescenceHydrogen bondCatalysisPolymerBiochemistrySinglet statePhysicsQuantum mechanicsNuclear physicsLuminescence and Fluorescent MaterialsNanoplatforms for cancer theranosticsPorphyrin and Phthalocyanine Chemistry