An Imine Photocyclization as an Alternative to the Pictet–Spengler Reaction for the Synthesis of AzaBenzannulated Perylenediimide Dyes
Antoine Goujon, Lou Rocard, Thomas Cauchy, Piétrick Hudhomme
Abstract
AzaBenzannulated perylenediimide (AzaBPDI) dyes were synthesized in high yields via a new reaction sequence involving an imine condensation followed by visible light-induced photocyclization. The large scope and efficiency of this alternative to the Pictet-Spengler reaction are demonstrated, allowing easy preparation of dimeric AzaBPDI as potential non-fullerene acceptors for organic solar cells.
Topics & Concepts
IminePictet–Spengler reactionCondensation reactionChemistryCondensationPhotochemistryOrganic chemistryCombinatorial chemistryCatalysisThermodynamicsPhysicsOrganic Electronics and PhotovoltaicsPhotochromic and Fluorescence ChemistryLuminescence and Fluorescent Materials