Preparation and photoisomerization process of dinaphthalene azobenzene cyclic chiral dopant

Meng-yi ZHOU; Hong-bo LU; Xue-wen XIE; Le YANG; Xiao XU; Jun ZHU; Guo-bing ZHANG; Long-zhen QIU

doi:10.3788/YJYXS20193405.0465

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Preparation and photoisomerization process of dinaphthalene azobenzene cyclic chiral dopant

Materials and Devices | 更新时间：2020-07-05

- Preparation and photoisomerization process of dinaphthalene azobenzene cyclic chiral dopant
- Chinese Journal of Liquid Crystals and Displays Vol. 34, Issue 5, Pages: 465-471(2019)
- 作者机构：
  
  特种显示技术国家工程实验室现代显示技术省部共建国家重点实验室培育基地, 合肥工业大学光电技术研究院, 安徽合肥 230009
- 作者简介：
- 基金信息：
- DOI：10.3788/YJYXS20193405.0465
  CLC： O753.2;TB34
- Received：10 January 2019，
  
  Accepted：30 January 2019，
  
  Published：2019-05
- 稿件说明：
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Meng-yi ZHOU, Hong-bo LU, Xue-wen XIE, et al. Preparation and photoisomerization process of dinaphthalene azobenzene cyclic chiral dopant[J]. Chinese journal of liquid crystals and displays, 2019, 34(5): 465-471.
DOI：

Meng-yi ZHOU, Hong-bo LU, Xue-wen XIE, et al. Preparation and photoisomerization process of dinaphthalene azobenzene cyclic chiral dopant[J]. Chinese journal of liquid crystals and displays, 2019, 34(5): 465-471. DOI： 10.3788/YJYXS20193405.0465.

摘要

环状光敏手性剂不仅具有较好的光稳定性，且可以通过控制环张力而对分子的光异构化速率进行调控，但其与液晶分子间的相容性有待提高。本文通过在联萘基团的6，6'位点处引入与液晶分子结构相似的棒状刚性取代基，制备了BPO5BA联萘偶氮苯环状光敏手性剂，探究了其在溶液和液晶中的光异构化过程，并通过计算Teas溶解度参数对手性剂分子与液晶分子间的相容性进行探究。通过研究发现，与Azo-o-Bi分子相比，BPO5BA分子中由于刚性取代基的引入，使偶氮苯基团的转动受到了环张力和刚性的限制，导致该分子在溶剂和液晶中的光异构化程度较低。此外，BPO5BA分子具有与Azo-o-Bi分子相反螺旋方向和较大的

值，且与液晶分子间的相容性较好。

Abstract

The cyclic photosensitive chiral dopant has not only better photostability

but also the photoisomerization rate of the molecule

which can be regulated by controlling the ring tension. However

the compatibility between the cyclic molecule and CLCs needs to be improved. In this paper

naphthalene azobenzene cyclic photosensitive chiral dopant BPO5BA was prepared by introducing rod-like rigid substituents at the 6

6' positions of the naphthalene group

which were similar to the molecular structure of the liquid crystal. The photoisomerization processes in solution and CLCs were investigated

as well as the compatibility between BPO5BA molecule and CLCs was estimated by calculating Teas parameters. Compared with Azo-o-Bi molecule

the rotation of azobenzene group in BPO5BA is limited by the ring tension and rigidity

due to the introduction of rigid group

resulting in a low degree of photoisomerization. In addition

BPO5BA molecule has an opposite helical direction and larger

value

and has good compatibility with CLCs.

关键词

Keywords

references

李昌立, 孙晶, 蔡红星, 等.胆甾相液晶的光学特性[J].液晶与显示, 2002, 17(3):193-198.

LI C L, SUN J, CAI H X, et al . Optical properties of cholesteric liquid crystals[J]. Chinese Journal of Liquid Crystals and Displays , 2002, 17(3):193-198. (in Chinese)

SHARMA V, CRNE M, PARK J O, et al . Structural origin of circularly polarized iridescence in jeweled beetles[J]. Science , 2009, 325(5939):449-451.

LU H B, XIE X Y, XING J, et al . Wavelength-tuning and band-broadening of a cholesteric liquid crystal induced by a cyclic chiral azobenzene compound[J]. Optical Materials Express , 2016, 6(10):3145-3158.

MCCONNEY M E, TONDIGLIA V P, HURTUBISE J M, et al . Photoinduced hyper-reflective cholesteric liquid crystals enabled via surface initiated photopolymerization[J]. Chemical Communications , 2011, 47(1):505-507.

JIN O Y, FU D W, WEI J, et al . Light-induced wide range color switching of liquid crystal blue phase doped with hydrogen-bonded chiral azobenzene switches[J]. RSC Advances , 2014, 4(54):28597-28600.

BISOYI H K, LI Q. Light-directing chiral liquid crystal nanostructures:from 1D to 3D[J]. Accounts of Chemical Research , 2014, 47(10):3184-3195.

张智勇, 陈元模, 张宏伟, 等.显示用胆甾相液晶材料发展现状[J].液晶与显示, 2003, 18(5):317-324.

ZHANG Z Y, CHEN Y M, ZHANG H W, et al . Progress of cholesteric liquid crystal materials for display[J]. Chinese Journal of Liquid Crystals and Displays , 2003, 18(5):317-324. (in Chinese)

LI Y N, WANG M F, WHITE T J, et al . Azoarenes with opposite chiral configurations:light-driven reversible handedness inversion in self-organized helical superstructures[J]. Angewandte Chemie International Edition , 2013, 52(34):8925-8929.

WHITE T J, BRICKER R L, NATARAJAN L V, et al . Phototunable azobenzene cholesteric liquid crystals with 2000 nm range[J]. Advanced Functional Materials , 2009, 19(21):3484-3488.

KIM Y, TAMAOKI N. Asymmetric dimers of chiral azobenzene dopants exhibiting unusual helical twisting power upon photoswitching in cholesteric liquid crystals[J]. ACS Applied Materials & Interfaces , 2016, 8(7):4918-4926.

WANG Y, URBAS A, LI Q. Reversible visible-light tuning of self-organized helical superstructures enabled by unprecedented light-driven axially chiral molecular switches[J]. Journal of the American Chemical Society , 2012, 134(7):3342-3345.

KIM Y, TAMAOKI N. A photoresponsive planar chiral azobenzene dopant with high helical twisting power[J]. Journal of Materials Chemistry C , 2014, 2(43):9258-9264.

SIEWERTSEN R, NEUMANN H, BUCHHEIM-STEHN B, et al . Highly efficient reversible Z-E photoisomerization of a bridged azobenzene with visible light through resolved S 1 (nπ*) absorption bands[J]. Journal of the American Chemical Society , 2009, 131(43):15594-15595.

MATHEWS M, TAMAOKI N. Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals[J]. Journal of the American Chemical Society , 2008, 130(34):11409-11416.

GOH M, AKAGI K. Powerful helicity inducers:axially chiral binaphthyl derivatives[J]. Liquid Crystals , 2008, 35(8):953-965.

VINVOGRADOV V, KHIZHNYAK A, KUTULYA L, et al . Photoinduced charge of cholesteric Lc-pitch[J]. Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics , 1990, 192(1):273-278.

TAKAISHI K, KAWAMOTO M. Synthesis and conformation of substituted chiral binaphthyl-azobenzene cyclic dyads with chiroptical switching capabilities[J]. Molecules , 2011, 16(2):1603-1624.

GOTO H, TOGASHI F, TSUJIMOTO A, et al . Cholesteric liquid crystal inductive asymmetric polymerisation of thiophene monomers[J]. Liquid Crystals , 2008, 35(7):847-856.

STEFANIS E, PANAYIOTOU C. Prediction of Hansen solubility parameters with a new group-contribution method[J]. International Journal of Thermophysics , 2008, 29(2):568-585.

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Related Institution

School of Materials Science and Engineering, University of Science and Technology Beijing

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School of Materials Science and Technology, Wuhan University of Technology, Wuhan 430070, China, E-mail:hechanghai63@163.

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