Enhancement of electro-optic activity by introduction of a benzyloxy group to conventional donor-π-acceptor molecules

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

doi:10.1016/j.orgel.2011.03.010

Cited by 43 publications

(27 citation statements)

References 20 publications

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“…Depending on different structures, the synthesized NLO chromophores exhibited a similar π→π* intramolecular charge-transfer (ICT) absorption band in the visible region. It was found that all of the three chromophores showed very large bathochromic shifts of 85 nm, 76 nm and 73 nm respectively, when solvent was changed from dioxane to chloroform, displaying larger solvatochromism than that of CLD (60 nm) 24 and a similar single donor FTC (61 nm) 25 chromophore. 2, chromophore CL, CL1 and CL2 exhibited the maximum absorption (λ max ) from 703 nm to 709 nm in chloroform.…”

Section: Optical Propertiesmentioning

confidence: 99%

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Liu

Zhang

et al. 2015

J. Mater. Chem. C

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Three novel second order nonlinear optical (NLO) chromophores based on julolidinyl donors and tricyanofuran (TCF) acceptors linked together via modified polyene π-conjugation with rigid benzene derivative steric hindrance groups (chromophores CL1 and CL2) or unmodified polyene π-conjugation (chromophores CL) moieties as the bridges have been synthesized in good overall yields and systematically characterized. Density functional theory (DFT) was used to calculate the HOMO-LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. Besides, to determine the redox properties of these chromophores, cyclic voltammetry (CV) experiments were performed. Comparied with CL, after introducting benzene derivative steric hindrance groups into the bridge, chromophores CL1 and CL2 had good thermal stabilities with high thermal decomposition temperatures which were 32°C, 24°C higher than chromophore CL, respectively. Most importantly, the introduction of rigid steric hindrance groups can effectively reduce dipole-dipole interactions to translate their relatively small β values into bulk high EO activities. By doping chromophores CL, CL1 and CL2 with a high loading of 45 wt % in APC, EO coefficients (r33) of up to 121, 197 and 202 pm V -1 at 1310 nm can be achieved, respectively. The r33 values of new chromophores CL1 and CL2 were about 1.6 times of chromophore CL. The high r33 value, good thermal stability and high yield suggest the potential use of the new chromophores in nonlinear optical area.

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Section: Optical Propertiesmentioning

confidence: 99%

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Liu

Zhang

et al. 2015

J. Mater. Chem. C

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“…26 In the geometry optimized structure of chromophore 14, we nd the oxygen atom in the methoxy group forms a hydrogen bond with the vinyl hydrogen. 14 vs. 3), and an obvious increase in dipole moment (cf.…”

Section: Substituted Triarylamine Moietiesmentioning

confidence: 99%

“…However, compared to their alkyl counterparts, TAA based chromophores usually exhibit reduced hyperpolarizabilities due to delocalization of the nitrogen lone pair into the two phenyl rings which do not connect with the bridge 8 and a lower EO coefficient, which may be due to p-p stacking interactions and charge transport between chromophores. 10,[26][27][28][29] To the best of our knowledge, a detailed understanding of the relationship between NLO properties and the electronic and geometric structures of the TAA donor subunit of chromophores is lacking. In order to optimize NLO chromophore hyperpolarizability, signicant theoretical and experimental efforts have been focused on modifying conjugated bridges [17][18][19][20][21][22][23][24] and the structure of electron acceptors.…”

Section: Introductionmentioning

confidence: 99%

Towards an understanding of structure-nonlinearity relationships in triarylamine-based push-pull electro-optic chromophores: the influence of substituent and molecular conformation on molecular hyperpolarizabilities

Wilson

Smith

et al. 2014

J. Mater. Chem. C

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We calculated the second-order hyperpolarizability (b) of a series of triarylamine (TAA) based donorbridge-acceptor (D-p-A) push-pull type nonlinear optical (NLO) chromophores with different electron donor moieties and the same thiophene p-bridge and dicyanovinyl electron acceptor using a timedependent Hartree-Fock (TDHF) approach within the software package MOPAC 2012. NLO chromophores with various quantities and positions of methoxy groups in the TAA donor moiety were investigated. The relationship between NLO properties and the electronic or geometric structures of the TAA donor subunit is discussed through the calculation results. Both substituent and conformational effects affect the delocalization of the nitrogen lone pair into the aryl rings, leading to a dramatic influence on the nonlinear optical properties. Introduction of methoxy groups at the ortho positions of the TAA moiety has a larger influence on the molecular hyperpolarizability and dipole moment than the introduction of methoxy group at the para or meta positions. Our calculation results demonstrate how to improve the NLO properties of TAA based chromophores while meeting practical device requirements. ; Fax: +1 972 883 2925; Tel: +1 972 883 5323 † Electronic supplementary information (ESI) available: All input les of model chromophores and all calculation results. See

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“…Compared with the FTC chromophore whose energy gap is 1.53 eV. 25 The introduction of benzo[b]thiophene ring at the donor end could effectively reduce the energy gap by 0.34 eV of chromophore B. Based on the "two level model", chromophore B with lower energy gap indicates the p-electron delocalization efficiency and may get a larger molecular hyperpolarizability (b).…”

Section: Synthesismentioning

confidence: 99%

Novel NLO-phores containing dihexyl amino benzo[b]thiophene exhibiting good transparency and enhanced electro-optical activity

Zhang

Peng

et al. 2014

RSC Adv.

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Two new chromophores (A and B) were synthesized, in which a benzo [b]thiophene moiety was first introduced as a donor group. To investigate the macroscopic EO activity of the new chromophores, guest-host doped polymer films were fabricated by doping chromophores A and B into amorphous polycarbonate (APC). The poled films containing A with a loading density of 20 wt% achieved a maximum EO coefficient (r 33 ) of 42 pm V À1 at 1310 nm, while for the poled films containing B, the r 33 value is 75 pm V À1 at 1310 nm. UV-vis spectral absorption of the new chromophores were studied in solutions and films, and chromophores A and B showed a maximum absorption in chloroform of 658 nm and 688 nm, respectively. Compared to the FTC (r 33 ¼ 20-50 pm V À1 at 1310 nm, l max ¼ 685 nm in chloroform) analogues, they exhibited enhanced electro-optical activity together with a high optical gap.This new type of chromophore provided better optimization of the nonlinearity-transparency trade-off.

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Enhancement of electro-optic activity by introduction of a benzyloxy group to conventional donor-π-acceptor molecules

Cited by 43 publications

References 20 publications

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Towards an understanding of structure-nonlinearity relationships in triarylamine-based push-pull electro-optic chromophores: the influence of substituent and molecular conformation on molecular hyperpolarizabilities

Novel NLO-phores containing dihexyl amino benzo[b]thiophene exhibiting good transparency and enhanced electro-optical activity

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