Axially chiral thiophene scaffolds: configurational stability and circularly polarized luminescence

Abstract

A new type of axially chiral compound, 3,3′-bidithieno[2,3-b:3′,2′-d]thiophene (BDTT), bearing aryl groups (BDTT-Ars) was synthesized and enantiomerically resolved. The racemization of enantiomers showed that their inversion barriers (ΔG) are in the range of 17.32–29.73 kcal mol⁻¹. Among them, BDTT-9An exhibited exceptional circularly polarized luminescence (CPL) properties, achieving a luminescence dissymmetry factor ∣g_lum∣ up to 10⁻². This work provides critical theoretical insights into non-benzenoid axial chirality in novel optoelectronic materials.