Rational design, facile synthesis, and linear/nonlinear optical properties of novel two-photon absorption stilbene derivatives with different configurations

Abstract

Four novel two-photon absorption compounds (1MOBI, 2MOHA, 3BrBI, and 4BrHA), which have assembled stilbene π-bridge, different electron acceptors and donors, were synthesized conveniently via the one-step Horner-Wadsworth-Emmons reaction. Their configurations are A-π-D-π-A, D′-π-D-π-D′, A′-π-A-π-A′, and D-π-A-π-D, respectively. Their linear and nonlinear optical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. The results demonstrate that the compounds with dihexylamino donors exhibit good optical properties. 2MOHA and 4BrHA exhibit large two-photon absorption cross-sections (2183 and 1737 GM) in DMF, which are larger than those of many known stilbene derivatives. The relationships between the structures and the optical properties were studied aided with the time-dependent density functional theory calculations.