Aggregation-induced emission from optically active X-shaped molecules based on planar chiral [2.2]paracyclophane

Abstract

An optically active π-stacked molecule was synthesized incorporating planar chiral [2.2]paracyclophane and o-carborane units to impart circularly polarized luminescence and aggregation-induced emission properties to the molecule. The molecule exhibited a strong emission from the aggregated state in a mixed solvent system (H2O/THF) and the solid state in the PMMA matrix. In the aggregated state, weak circularly polarized luminescence was observed owing to the random intermolecular orientation. On the other hand, the circularly polarized luminescence was clearly observed in the PMMA film containing 1 wt% molecule. Theoretical studies using time-dependent density functional theory reproduced the molecule’s circular dichroism and circularly polarized luminescence properties.