New p-azaquinodimethane core based narrow-gap non-ring fused organic acceptor†

Abstract

The design and synthesis of sAQM-1, a para-azaquinodimethane-based non-ring fused organic π-conjugated molecule with an undemanding, metal-free synthetic route, is reported. sAQM-1 exhibits a narrow optical gap, stabilized frontier molecular orbitals, strong intramolecular charge transfer, and tunable self-assembly properties. Compared to the ring-fused Y6 acceptor, electronic energy levels are stabilized, and optical absorption red-shifted, demonstrating the potential of quinoidal scaffolds delivering atom economy and leading to narrow-gap organic electronic materials.