Silver-mediated, direct phosphorylation of BODIPY dyes at the 3- or 3,5-positions with H-phosphonates
Fan Lv, Heng Li, Qinghua Wu, Xing Guo, Hongtao Zhang, Changjiang Yu, Lijuan Jiao, Erhong Hao
Abstract
A direct and regioselective C-H/P-H cross-coupling of dialkyl phosphites, and diphenylphosphine oxide to easily available BODIPYs through an Ag-mediated radical addition, resulted in a series of new α-phosphorylated BODIPY fluorophores under mild conditions. Hydrolysis of the phosphonate gave the corresponding BODIPY phosphoric acid, which is soluble and fluorescent in water with a high quantum yield of 0.83.
Topics & Concepts
BODIPYChemistryPhosphonateRegioselectivityQuantum yieldYield (engineering)Phosphoric acidFluorescencePhotochemistryHydrolysisPhosphorylationDiphenylphosphine oxideMedicinal chemistryOrganic chemistryBiochemistryMaterials scienceCatalysisQuantum mechanicsMetallurgyPhysicsLuminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionPorphyrin and Phthalocyanine Chemistry