Abstract
Optically active fullerenes (C76, C82, C84), including C60 and C70 derivatives carrying organic substituents, possess various potent applications because of unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality has not yet been elucidated because of a very poor quantum yield of fluorescence (FL). With this background in mind, we synthesized new chiral C70 derivatives, X70A, solely by reacting bis-borylated xanthene with C70 in a one-step double addition reaction with 20% yield, followed by a successful optical resolution using a recyclable chiral-HPLC technique. The isolated X70A enantiomers were confirmed by their mirror-image circular dichroism spectra in the range of 300 nm and 700 nm. The enantiomeric pair of X70A in toluene revealed clearly mirror-image circularly polarized luminescence (CPL) spectra with a high |glum| value of 7.0 × 10–3 at 690 nm associated with FL lifetime of 0.99 ns. The deep-red CPL of X70A should provide new photofunctionality as chiral nanocarbon materials.
π-Expanded Axially Chiral Biaryls and Their Emissions: Molecular Design, Syntheses, Optical Resolution, Absolute Configuration, and Circularly Polarized Luminescence of 1,1′-Bipyrene-2,2′-diols
