Synthesis and liquid crystalline phase behavior investigation of triphenylene acrylate intermediates

Bin MU; Ke-yang CHEN; Dong-zhong CHEN

doi:10.3788/YJYXS20173206.0424

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Synthesis and liquid crystalline phase behavior investigation of triphenylene acrylate intermediates

Invited Paper | 更新时间：2020-07-07

- Synthesis and liquid crystalline phase behavior investigation of triphenylene acrylate intermediates
- Chinese Journal of Liquid Crystals and Displays Vol. 32, Issue 6, Pages: 424-432(2017)
- 作者机构：
  
  南京大学化学化工学院生命化学协同创新中心高分子科学与工程系及高性能高分子材料与技术教育部重点实验室, 江苏南京 210023
- 作者简介：
- 基金信息：
- DOI：10.3788/YJYXS20173206.0424
  CLC： TP394.1;TH691.9
- Received：09 December 2016，
  
  Accepted：20 January 2017，
  
  Published：05 June 2017
- 稿件说明：
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Bin MU, Ke-yang CHEN, Dong-zhong CHEN. Synthesis and liquid crystalline phase behavior investigation of triphenylene acrylate intermediates[J]. Chinese journal of liquid crystals and displays, 2017, 32(6): 424-432.
DOI：

Bin MU, Ke-yang CHEN, Dong-zhong CHEN. Synthesis and liquid crystalline phase behavior investigation of triphenylene acrylate intermediates[J]. Chinese journal of liquid crystals and displays, 2017, 32(6): 424-432. DOI： 10.3788/YJYXS20173206.0424.

摘要

本文主要报道了一系列不对称取代的苯并菲丙烯酸酯类盘状液晶中间体化合物的合成及其液晶相行为研究。首先，从单羟基苯并菲类衍生物出发，针对不同长度烷基间隔基体系的反应活性差异，采用不同方法引入可聚合丙烯酸酯基官能团，对亚甲基间隔基数目从0到10的苯并菲丙烯酸酯进行全系列合成，并通过核磁共振波谱（NMR）和质谱（MS）对合成目标产物进行化学结构确认。通过差示扫描量热法（DSC）、偏光显微镜（POM）和小角/广角X射线散射（SAXS/WAXS）表征并分析该系列盘状苯并菲丙烯酸酯中间体的液晶相行为及组装的柱状有序结构。结果表明，大多数己氧基苯并菲类丙烯酸酯中间体只形成结晶；而丁氧基苯并菲类中间体则大都能呈现单向或双向互变型热致六方柱状液晶相，以及一类典型的具有三维（3D）位置有序的六方柱状塑晶相。该类不对称取代的苯并菲丙烯酸酯盘状液晶相态结构与相行为关系的阐明，将对（甲基）丙烯酸酯类可聚合功能性单体的设计合成以及加深对聚合制得侧链盘状液晶聚合物的多级有序相结构的认识和理解具有重要意义。

Abstract

We present a systematical investigation on the synthesis

molecular characterization and liquid crystalline phase behaviors of a series of triphenylene (TP) acrylate intermediates. Based on different reaction activity of variant length of polymethylene spacer

several synthetic protocols have been successfully employed for introducing an acrylate group to the TP core via polymethylene spacer with the methylene number from 0 to 10. The obtained polymerizable TP acrylate intermediates were confirmed by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). Furthermore

differential scanning calorimetry (DSC)

polarized optical microscopy (POM) and small-and wide-angle X-ray scattering (SAXS/WAXS) were employed to explore the thermotropic liquid crystalline phase behavior and detailed columnar organizations of the series TP intermediates. Most of the TP acrylates with hexyloxy substituents only exhibited crystalline solid phase

while those with butoxy peripheral groups displayed monotropic or enantiotropic hexagonal columnar liquid crystalline mesophases with one example showing three-dimensional (3D) positionally ordered hexagonal columnar plastic phase. Herein the comprehensive synthesis and systematical comparison study on their liquid crystalline phase behaviors of the series discotic TP acrylate intermediates with variant length spacers would be helpful for guiding the design and preparation of other polymerizable functional (meth)acrylate monomers

and also enhance the in-depth understanding of various hierarchical structures of discotic columnar liquid crystalline polymer materials.

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references

KAWATA K. Orientation control and fixation of discotic liquid crystal [J].The Chemical Record, 2002, 2(2): 59-80.

KUMAR S.Chemistry of Discotic Liquid Crystals: From Monomers to Polymers [M]. Boca Raton: CRC Press, 2010.

WÖHRLE T, WURZBACH I, KIRRES J, et al. Discotic liquid crystals [J]. Chemical Reviews, 2016, 116(3): 1139-1241.

SERGEYEV S, PISULA W, GEERTS Y H. Discotic liquid crystals: a new generation of organic semiconductors [J].Chemical Society Reviews, 2007, 36(12): 1902-1929.

KAAFARANI B R. Discotic liquid crystals for opto-electronic applications [J].Chemistry of Materials, 2011, 23(3): 378-396.

隋岩, 郭剑, 李正强, 等.苯并菲类盘状液晶的合成及应用[J].液晶与显示, 2016, 31(1):40-46.

SUI Y, GUO J, LI Z Q, et al. Synthesis and application of triphenylene discotic liquid crystals [J]. Chinese Journal of Liquid Crystals and Displays, 2016, 31(1): 40-46. (in Chinese)

WU B, MU B, WANG S, et al. Triphenylene-based side chain liquid crystalline block copolymers containing a PEG block: controlled synthesis, microphase structures evolution and their interplay with discotic mesogenic orders [J]. Macromolecules, 2013, 46(8): 2916-2929.

MU B, WU B, PAN S, et al. Hierarchical self-organization and uniaxial alignment of well synthesized side-chain discotic liquid crystalline polymers [J]. Macromolecules, 2015, 48(8): 2388-2398.

MU B, PAN S, BIAN H F, et al. Well-organized columnar superlattices via positive coupling between polymer backbone and discotic side groups [J]. Macromolecules, 2015, 48(19): 6768-6780.

MU B, LI Q, LI X, et al. Cyclic polymers with pendant triphenylene discogens: convenient synthesis and topological effect on thermotropic liquid crystal behavior and fluorescence enhancement [J]. Polymer Chemistry, 2016, 7(39): 6034-6038.

WANG X J, ZHOU Q F.Liquid Crystalline Polymers [M]. Singapore: World Scientific Publishing, 2004.

TIAN L, YANG Y L, WYSOCKI L M, et al. Selective esterase-ester pair for targeting small molecules with cellular specificity [J]. Proceedings of the National Academy of Sciences of the United States of America, 2012, 109(13): 4756-4761.

KONG X F, HE Z Q, ZHANG Y N, et al. A mesogenic triphenylene-perylene-triphenylene triad [J]. Organic Letters, 2011, 13(4): 764-767.

KONG X F, HE Z Q, GOPEE H, et al. Synthesis and liquid crystal properties of triphenylene liquid crystals bearing polymerisable acrylate and methacrylate groups [J]. Liquid Crystals, 2011, 38(8): 943-955.

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