Synthesis and comparative studies of coumarin-based nonlinear optical chromophores with different conjugated electron bridge

Abstract

Two novel nonlinear optical (NLO) chromophores JC-T-TCF and JC-F-TCF utilizing tetramethyljulolidine-based coumarin and tricyanofuran(TCF) as the electron donor and acceptor, respectively, were designed and synthesized. The two chromophores were linked with different π conjugated electron bridge (thiophene group and furan group), which provide the opportunity to study the structure–property relationship of coumarin-based chromophores. Both the novel obtained chromophores exhibited reasonable stability and solvatochromic effect. The theoretical calculation results indicated that both chromophores possess microscopic hyperpolarizability (β) in excess of 320 × 10−30esu, and the chromophore JC-T-TCF utilizing thiophene group as the electron bridge exhibited obviously larger β value (456.8 × 10−30esu). The larger β value, combination with the larger µ value, endowed JC-T-TCF with larger electro-optic activity of 70 pm V−1 at the wavelength of 1310 nm in the guest–host films of chromophores doped into PMMA, which provide the potential application opportunity in the field of optical waveguide devices.