Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling To Build Nonstacking Fluorophores

Abstract

Triazoliptycene fluorophores have been designed and synthesized, in which a three-dimensional propeller -like iptycene motif is employed to suppress intermolecular pi-pi stacking in the solid state. Key to the success of this modular synthesis is a stereoelectronic bias imposed by the iptycene scaffold, which assists the desired regioselectivity in the C-N cross-coupling step as the last stage structure diversification from a common precursor.