Fluorous Corannulenes: Ab initio Predictions and the Synthesis of sym-Pentafluorocorannulene

Abstract

Ten sym-penta and deca-X substituted corannulenes (1–10; X=H, F, CH3, or CF3) define a library of fluorous compounds comprising high symmetry non-planar aromatic compunds. They provide a group of structurally similar, yet physically distinct structures manifesting special chemical behavior related to their degree of fluorination. Owing to their bowl forms, corannulene derivatives are distinct from planar polynuclear aromatic compounds; they have relatively high dipole moments, accept 1–4 electrons, and display room temperature fluorescence as well as low temp phosphorescence. Electronic structure theory predicts the bowl inversion barrier and physical properties. The syntheses of sym-pentafluorocorannulene by an efficient late stage fluorination affords a key derivative to calibrate predictions.