Development of Carbazole-Cored Organo-Photocatalyst for Visible Light-Driven Reductive Pinacol/Imino-Pinacol Coupling
Samrat Kundu, Lisa Roy, Modhu Sudan Maji
Abstract
Benzoperylenocarbazole (BPC), a unique carbazole-based organophotocatalyst, is reported herein as a potent organo-photoreductant. Lower excited state oxidation potential (-2.0 V vs SCE) and reasonable excited state lifetime (4.61 ns) render BPC an effective photosensitizer. Under irradiation of blue light employing low catalyst loading (0.5 mol %), a plethora of vicinal diols and diamines were synthesized in excellent yields through reductive coupling of carbonyls and imines, respectively. Insight about the electronic structure of BPC was obtained by DFT calculations.
Topics & Concepts
ChemistryPinacolCarbazolePhotosensitizerPhotochemistryVicinalExcited statePhotocatalysisCatalysisOrganic chemistryNuclear physicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques