Facile synthesis of extended TPA-quinazolinone derivatives and the nonlinear optical properties

Abstract

In this work, four new quinazolinone (QZ)-based compounds containing triphenylamine (TPA) moiety have been synthesized, defined as QZC, QZC-1, QZC-2, QZC-3, for the application of third-order nonlinear optical (NLO) responses. A new design of two-step synthesis has been put forward, the first step is Ullmann reaction with QZ, and the second is connecting QZ and the substituted triphenylamines (TPAs) through a Suzuki cross-coupling reaction to afford the target products. Electrochemical measurement data indicated that the tuning of the HOMO and LUMO energy levels can be easily achieved by introducing and modifying the donor moiety. The NLO properties were evaluated by the Z-scan technique which showed that introduction of a benzene ring as a π bridge could reduce the transmission energy of electrons from a ground state to an excited state, and the added methoxy in TPA moiety could promote the ICT, and improve the third-order NLO properties of molecules. Theoretical calculations matched well with the electrochemical information and NLO information. The results suggest that the materials based on QZ have potential applications in integrated NLO devices.