Using phenoxazine and phenothiazine as electron donors for second-order nonlinear optical chromophore: Enhanced electro-optic activity

Liu, Fenggang; Wang, Haoran; Yang, Yuhui; Xu, Huajun; Yang, Dan; Bo, Shuhui; Liu, Jialei; Zhen, Zhen; Liu, Xinhou; Qiu, Ling

doi:10.1016/j.dyepig.2014.11.015

Cited by 53 publications

(21 citation statements)

References 52 publications

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“…The spectral data are summarized in Table 1. 24 This result shows that N-(4-dimethylaminophenyl) substituent provides extra donating strength to the donor part, shifting the CT absorption band of the chromophore to lower energy. Chromophores L1 and L2 were red-shifted in their absorption spectra, compared to the traditional chromophore FTC, probably due to the stronger donor tetrahydroquinoline.…”

Section: Optical Propertiesmentioning

confidence: 90%

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: Optical Propertiesmentioning

confidence: 90%

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

et al. 2015

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“…In comparison with inorganic NLO crystals such as lithium niobate, organic or organometallic NLO chromophores have many advantages such as a lower cost, larger and faster NLO responses. [10][11][12] Second order NLO properties require the absence of centrosymmetry and generally the second order NLO chromophores are based on an electron-donating group (D) and an electron-withdrawing group (A) linked by a π-conjugated bridge (D-π-A). [10][11][12][13][14][15] properties are directly related to the intramolecular charge transfer (ICT) occurring in such structures and can be easily tuned by varying the nature of the donor/acceptor couple and the π-conjugated spacer.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…[10][11][12] Second order NLO properties require the absence of centrosymmetry and generally the second order NLO chromophores are based on an electron-donating group (D) and an electron-withdrawing group (A) linked by a π-conjugated bridge (D-π-A). [10][11][12][13][14][15] properties are directly related to the intramolecular charge transfer (ICT) occurring in such structures and can be easily tuned by varying the nature of the donor/acceptor couple and the π-conjugated spacer. [16][17][18] In our group, we have recently optimized the NLO properties of chromophores based on pyrimidine [19][20][21][22][23][24] and/or pyranylidene [22][23][24][25][26][27] moieties as electron-withdrawing and electrondonating fragments respectively.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Incorporation of a ferrocene unit in the π-conjugated structure of donor-linker-acceptor (D-π-A) chromophores for nonlinear optics (NLO)

et al. 2018

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In this paper we describe the synthesis, the electrochemical behaviour as well as the linear and nonlinear optical (NLO) properties of two push-pull derivatives bearing pyranylidene electron donating fragment, pyrimidine/methyl pyrimidinium electron withdrawing moiety and a ferrocene part in the π-conjugated bridge. The properties of these two compounds were compared to their analogues without ferrocene or pyranylidene fragments. Experimental results were completed with DFT calculations to gain further insight into the intramolecular charge transfer (ICT). All the results indicate a significant charge transfer through the ferrocene unit. The ICT is however more limited than in all organic analogues. Highlights • Ferrocene unit was incorporated in the π-conjugated linker or D-π-A compounds. • Intramolecular charge transfer through ferrocene moiety was studied. • Electrochemical and photophysical properties were compared with all organic analogues. • The ferrocene unit limits charge transfert from donor to acceptor.

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“…As the essential component in integrated optics, organic nonlinear optical materials have witnessed increasing research interests recently due to their easier synthetic design, molecular flexibility and larger nonlinear optical coefficient when compared to their inorganic counterparts [1][2][3]. Generally, organic chromophores with electron donor (D)-p conjugate bridge-acceptor (A) molecular structure normally exhibit stronger charge transfer ability, thus the high performance electro-optic (E-O) devices can be fabricated by blending or grafting D-p-A type chromophores into host polymers, followed by spinning coating and electron poling process [4,5].…”

Section: Introductionmentioning

confidence: 99%

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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Using phenoxazine and phenothiazine as electron donors for second-order nonlinear optical chromophore: Enhanced electro-optic activity

Cited by 53 publications

References 52 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

Incorporation of a ferrocene unit in the π-conjugated structure of donor-linker-acceptor (D-π-A) chromophores for nonlinear optics (NLO)

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

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