Synthesis of Bis(N,N-diethyl)aniline-Based, Nonlinear, Optical Chromophores with Increased Electro-Optic Activity by Optimizing the Thiolated Isophorone Bridge

Six nonlinear, optical chromophores, Z1–Z6, based on the bis(N,N-diethyl)aniline-derived donor and thiolated isophorone bridge, were designed synthesized. The was applied in a chromophore with as an electron bridge for first time. In particular, parts of chromophores Z2–Z6 modified different functional groups, including tert-butyltrimethylsilane tert-butyl(methyl)diphenylsilane derivative: 1,3-bis(trifluoromethyl)benzene alkylaniline cyanoacetate, respectively. Density theory calculations suggested this series show much greater hyperpolarizability than traditional, due to strong ability. These showed very high poling efficiencies large steric hindrance chromophores. A efficiency (2.04 ± 0.08 nm2/V2) r33 value (193 pm/V) achieved polymeric thin films doped 25 wt% Z6 at 1310 nm.