Systematic Study on Nonlinear Optical Chromophores with Improved Electro-Optic Activity by Introducing 3,5-Bis(trifluoromethyl)benzene Derivative Isolation Groups into the Bridge

Abstract

A series of novel chromophores A, B, C, and D, based on the julolidinyl donor and the tricyanofuran (TCF) and CF3-tricyanofuran (CF3-Ph-TCF) acceptors, have been synthesized and systematically investigated. The 3,5-bis(trifluoromethyl)benzene derivative isolation group was introduced into the bridge in the chromophores C and D. These nonlinear optical chromophores showed good thermal stability, and their decomposition temperatures were all above 220 °C. Density functional theory (DFT) was used to calculate the energy gaps and first-order hyperpolarizability (β). The macroscopic electro-optic (EO) activity was measured using a simple reflection method. The highest EO coefficient of poled films containing 35 wt% of chromophore D doped in amorphous polycarbonate afforded values of 54 pm/V at 1310 nm. The results indicate that the 3,5-bis(trifluoromethyl)benzene isolation group can suppress the dipole–dipole interaction of chromophores. The moderate r33 value, good thermal stability, and good yield of chromophores suggest their potential use in the nonlinear optical area.

From Visible to Near–Infrared Light–Triggered Photochromism: Negative Photochromism

“…The quantum yield of the photoreaction of 102o was evaluated to be 0.24 [115]. This class of compounds is expected for use as sulfatase activity-based probe [116], synergistic phototherapy [117], nonlinear optical chromophores [118,119], and so on. low-acidity open isomer to the metastable high-acidity isomer 102c upon visible light irradiation (λ = 470 nm).…”

“…The quantum yield of the photoreaction of 102o was evaluated to be 0.24 [115]. This class of compounds is expected for use as sulfatase activity-based probe [116], synergistic phototherapy [117], nonlinear optical chromophores [118,119], and so on. Furthermore, a series of hydroxytricyanopyrrole (HTCP) acceptors based on the TCF structure have been reported by Fedoseev and coworkers.…”

“…The quantum yield of the photoreaction of 102o was evaluated to be 0.24 [ 115 ]. This class of compounds is expected for use as sulfatase activity–based probe [ 116 ], synergistic phototherapy [ 117 ], nonlinear optical chromophores [ 118 , 119 ], and so on.…”