Synthesis of two optically active V-shaped molecules: Investigating the correlation between the stacking angle and chiroptical properties

Abstract

This study demonstrates the synthesis of two optically active V-shaped molecules using enantiopure pseudo-ortho- and pseudo-meta-disubstituted [2.2]paracyclophane as the chiral building blocks. Both consist of the same π-electron system (p-phenylene-ethynylene containing three benzenes) stacked at the terminal benzene rings with stacking angles of 60° and 120°, respectively. The chiroptical properties, particularly the circularly polarized luminescence behavior, of the molecule with a stacking angle of 60° were better than those of its counterpart, and these results were confirmed via theoretical studies. A correlation exists between the chiroptical properties and stacking angle of emissive π-conjugated molecules.