Three series of high performance of nonlinear optical chromophores B-TCF, B-3F, B-5F, N-TCF, N-3F, N-5F, S-TCF, S-3F S-5F based on the triphenylamine or N, N-bis-(4-methoxyphenyl) aryl-amino donors, and tricyanofuran (TCF) or perfluorophenyl-tricyanofuran(5F-TCF) phenyl-trifluoromethyl-tricyanofuran(3F-TCF) acceptors linked together by tetraene or thiophene based bridges, we synthesized and investigated. We have systematically compared the nine chromophores composed of two kinds of donors and bridges and three kinds of acceptors to illustrate structure-performance relationships. DFT theoretical calculation and electro-optical coefficient test results show that electron-donor, p-conjugated bridge, and acceptor have a great influence on the performance of chromophore. The strength of the donor and acceptor and the electronic transmission capacity of the electronic bridge would affect the first-order hyperpolarizability of the chromophore and the r33 value of the chromophore. Polymeric thin films doped with 25wt% chromophore N-3F and N-5F with N, N-bis-(4-methoxyphenyl) aryl-amino donor have been poled to afford large r33 values of 198 and 171 pm/V at 1.31μm, respectively, which is much higher than the EO activity of chromophore B-TCF (31pm/V).

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