From benzyl to fluorenyl: Enhancing photostability and modulating optoelectronic properties of paraazaquinodimethanes

Abstract

Herein, we report the synthesis and the characterization of first fluorenyl-flanked para-azaquinodimethane (F-AQM), which exhibits markedly improved photostability, a pronounced bathochromic shift in absorption, and a reduced optical bandgap compared to the benzyl-flanked analogue (AQM1). Single-crystal Xray diffraction and theoretical calculations reveal a bent quinoidal core with twisted fluorenyl units, highlighting F-AQM as a promising quinoidal semiconductor building block.