Effect of modified donor units on molecular hyperpolarizability of thienyl-vinylene nonlinear optical chromophores

Zhang, Xianmin; Aoki, Isao; Piao, Xianqing; Inoue, Shin‐ichiro; Tazawa, Hidehisa; Yokoyama, Shiyoshi; Otomo, Akira

doi:10.1016/j.tetlet.2010.08.060

Cited by 55 publications

(21 citation statements)

References 25 publications

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“…In the past decades, many studies on NLO chromophores have mainly focused on the design of electron bridges and electron acceptors, while the donor units have remained relatively unchanged. 16,17 Some studies have shown that by introducing additional electron-rich heteroatom group into the donor moiety could effectively enhance nonlinear optical property. 12,15 Many works were focused on the optimization of these two donor groups by different kinds of modification.…”

Section: Introductionmentioning

confidence: 99%

Auxiliary donor for tetrahydroquinoline-containing nonlinear optical chromophores: enhanced electro-optical activity and thermal stability

et al. 2015

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A series of chromophores FTC, L1 and L2 has been synthesized based on three different types of electron donors, including diethylaminophenyl, tetrahydroquinolinyl and N-(4dimethylaminophenyl) tetrahydroquinolinyl groups respectively, with the same thiophene bridges and strong tricyanovinyldihydrofuran (TCF) acceptors. In particular, the donor part of the chromophore L2 was modified with additional donor N-(4-dimethylaminophenyl) substituent, resulting in enhanced thermal stability and electro-optic activity. Cyclic voltammetry measurements showed that chromophore L2 had smaller energy gap than chromophore L1 due to the additional donor. Moreover, Density functional theory calculations suggested that the molecular quadratic hyperpolarizability (µβ) value of chromophore L2 is 29% and 44% larger than that of chromophores L1 and FTC, respectively. The doped film containing the chromophore L2 showed an r 33 value of 100 pm/V at the concentration of 25 wt% which is much higher than the EO activity of the chromophore L1 (57 pm/V) and two times higher than that of the traditional chromophore FTC (39 pm/V).

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Section: Introductionmentioning

confidence: 99%

Auxiliary donor for tetrahydroquinoline-containing nonlinear optical chromophores: enhanced electro-optical activity and thermal stability

et al. 2015

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“…Therefore, we assumed that the mismatch between calculation and experiment supposed to mainly derived from the identification of dominate influence onto molecular second-order polarizability. Moreover, this kind of mismatch between theoretical calculation and experimental data has been also recorded in several published work from other groups [2,7,19]. Although the DFT calculation did lead to ambiguous conclusions sometimes, it is still widely used as a powerful tool to clarify the molecular configuration and charge transfer in NLO chromophores community.…”

Section: Microscopic Nonlinear Optical Propertiesmentioning

confidence: 97%

Effect of auxiliary electron-donating group on the microscopic nonlinear optical properties of vinyl and azobenzene based chromophores

Tang

Jia

Tang

et al. 2016

J Mater Sci: Mater Electron

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A series of organic nonlinear optical chromophores containing different auxiliary electron-donating groups (alkoxy, benzyloxy and alkyl) and p-conjugated bridges (vinyl and azobenzene) have been synthesized and systematically characterized using UV-Vis spectroscopy, density functional theory calculation and thermogravimetric analysis. The microscopic molecular hyperpolarizability was obtained via the simple solvatochromism method, where the synthesized chromophores were dissolved in several solvents with different refractive index for absorption spectra measurement. It was found that the introduction of auxiliary groups obviously improved the microscopic molecular hyperpolarizability of all the synthesized chromophores, especially for the benzyloxy modified azobenzene based chromophore, up to sevenfold enhancement of molecular hyperpolarizability as well as good visible light transmittance and thermal stability up to 247°C were obtained, which should be mainly attributed to the enhanced charge transfer enabled by the benzyloxy modification that is confirmed by the electron density distribution in the highest occupied molecular orbital and lowest unoccupied molecular orbital.

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“…Organic EO films prepared by APC doped by chromophore 6 have shown the largest EO coefficients magnitudes equal to 53 pm/V with 25 wt% chromophore loading density at 1310 nm. The EO activity is just improved up to 47%, however it is not still sufficiently large [44,45]. The addition of benzyl group was effective for the steric hindrance.…”

Section: Nlo Chromophores With Benzyloxy Julolidinyl Donormentioning

confidence: 97%

Optimization of polycyclic electron-donors based on julolidinyl structure in push–pull chromophores for second order NLO effects

et al. 2015

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Effect of modified donor units on molecular hyperpolarizability of thienyl-vinylene nonlinear optical chromophores

Cited by 55 publications

References 25 publications

Auxiliary donor for tetrahydroquinoline-containing nonlinear optical chromophores: enhanced electro-optical activity and thermal stability

Auxiliary donor for tetrahydroquinoline-containing nonlinear optical chromophores: enhanced electro-optical activity and thermal stability

Effect of auxiliary electron-donating group on the microscopic nonlinear optical properties of vinyl and azobenzene based chromophores

Optimization of polycyclic electron-donors based on julolidinyl structure in push–pull chromophores for second order NLO effects

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