Synthesis and Property of Oxymethylene-Bridged Bent-core Liquid Crystals

doi:10.6023/cjoc201301033

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 2010-2015.DOI: 10.6023/cjoc201301033 Previous Articles Next Articles

Notes

亚甲氧基桥键弯曲型液晶合成与性能研究

王勇丽^a, 杜琼^a, 王国华^a, 张智勇^a, 戴志群^a, 关金涛^a, 项颖^b

a 武汉轻工大学化学与环境工程学院武汉 430023;
b 广东工业大学信息工程学院广州 510006

收稿日期:2013-01-16 修回日期:2013-04-01 发布日期:2013-05-08
通讯作者: 张智勇 E-mail:zzy6211@126.com
基金资助:
国家自然科学基金(No.11074054);湖北省教育厅科技基金(Z20091801);武汉工业学院研究生教育创新基金(No. 2011cx003)资助项目

Synthesis and Property of Oxymethylene-Bridged Bent-core Liquid Crystals

Wang Yongli^a, Du Qiong^a, Wang Guohua^a, Zhang Zhiyong^a, Dai Zhiqun^a, Guan Jintao^a, Xiang Ying^b

a Department of Chemistry and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023;
b Department of Technology Institute and Information Engineering, Guangdong Polytechnic University, Guangzhou 510006

Received:2013-01-16 Revised:2013-04-01 Published:2013-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No.11074054), the Scientific Research Found of Hubei Provincial Education Department (No. 20091801) and the Educational and Innovative Foundation for the Graduate Students of Wuhan Polytechnic University (No. 2011cx003)

A novel series of bent-core molecules with a central bent core based on 2,5-bis(4-hydroxyphenyl)-1,3,4-oxadiazole, oxymethylene-bridged (CH₂O), and alkyl tails with carbon numbers m=3, 5, 6, 7, 8, 9, 10 were prepared. Structures of the titled compounds were confirmed by ¹H NMR, ¹³C NMR, IR, MS techniques, their transition temperatures and phase transition were investigated using differential scanning calorimetric (DSC) and polarizing optical microscopy (POM). Comparing with ester-bridged, target compounds 6a～6g have right chemical structure, possessed low melting points that below 100 ℃ (except 6c) and exhibited liquid crystal phases. Compounds 6d～6g exist wide phase temperature range and show odd-even effect.

Key words: bent-core liquid crystal, oxadiazol, oxymethylene, synthesis, low melting points

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Wang Yongli, Du Qiong, Wang Guohua, Zhang Zhiyong, Dai Zhiqun, Guan Jintao, Xiang Ying. Synthesis and Property of Oxymethylene-Bridged Bent-core Liquid Crystals[J]. Chin. J. Org. Chem., 2013, 33(9): 2010-2015.

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[1] Pelzl, G.; Wirth, I.; Weissflog, W. Liq. Cryst. 2001, 28, 969.
[2] Freiser, M. J. Phys. Rev. Lett. 1970, 24, 1041.
[3] Niori, T.; Sekine, T.; Watanabe, J.; Furukawa, T.; Takezoe, H. J. Mater. Chem. 1996, 6, 1231.
[4] Pelzl, G.; Diele, S.; Weissflog, W. Adv. Mater. 1999, 11, 9.
[5] Walba, D. M.; Korblova, E.; Shao, R. F.; Clark, N. A. J. Mater. Chem. 2001, 11, 2743.
[6] Link, D. R.; Natale, G.; Shao, R. F.; Maclenan, J. E.; Clark, N. A.; Korblova, E.; Walba, D. M. Science 1997, 278, 1924.
[7] Heppke, G.; Moro, D. Science 1998, 279, 1872.
[8] Ros, M. B.; Serrano, J. L.; Fuente, M. R.; Folcia, C. L. J. Mater. Chem. 2005, 15, 5093.
[9] Reddy, R. A.; Tschierske, C. J. Mater. Chem. 2006, 16, 907.
[10] Madsen, L. A.; Dingemans, T. J.; Nakata, M.; Samulski, E. T. Phys. Rev. Lett. 2004, 92, 145505-1.
[11] Acharya, B. R.; Primak, A.; Kumar, S. Phys. Rev. Lett. 2004, 92, 145506-1.
[12] Prasad, V.; Kang, S. W.; Suresh, K. A.; Joshi, L.; Wang, Q. B.; Kumar, S. J. Am. Chem. Soc. 2005, 127, 17224.
[13] Keith, C.; Lehmann, A.; Baumeister, U.; Prehm, M.; Tschierske, C. Soft Matter. 2010, 6, 1704.
[14] Dunemann, U.; Schroder, M. W.; Reddy, A.; Pelzl, G.; Diele, S.; Weissflog, W. J. Mater. Chem. 2005, 15, 4051.
[15] Weissflog, W.; Naumann, G.; Kosata, B.; Schroder, M. W.; Eremin, A.; Diele, S.; Vakhovskaya, Z.; Kresse, H.; Friedemann, R.; Krishnan, S. A.; Pelzl, G. J. Mater. Chem. 2005, 15, 4328.
[16] Michal, K.; Damian, P.; Milada, G.; Ewa, G. J. Mater. Chem. 2009, 19, 3153.
[17] Du, Q.; You, H.-J.; Wang, X.-Y.; Zhang, Z.-Y.; Dai, Z.-Q. Chin. J. Liq. Cryst. Disp. 2011, 26, 719 (in Chinese).
(杜琼, 游红军, 汪晓燕, 张智勇, 戴志群, 液晶与显示, 2011, 26, 719.)
[18] Shen, D.; Cai, L.-Z.; Shen, J.-W. Chin. J. Liq. Cryst. Disp. 2003, 18, 411 (in Chinese).
(沈冬, 蔡良珍, 沈晶伟, 液晶与显示, 2003, 18, 411.)
[19] Gray, G. W. Mol. Cryst. Liq. Cryst. 1979, 53, 147.
[20] Wen, J.-X.; Yin, H.-Y.; Chen, Q. Chin. Lett. Liq. Cryst. 1995, 3, 147 (in Chinese).
(闻建勋, 尹慧勇, 陈齐, 液晶通讯, 1995, 3, 147.)
[21] Osman, M. A. Mol. Cryst. Liq. Cryst. 1982, 82, 47.
[22] Found, B. J. Heterocycl. Chem. 1999, 36, 1029.
[23] Kidwai, M.; Mohan, R. Org. Prop. Proced. Intern. 2003, 35, 426.
[24] Balamururagan, R.; Kanan, P. J. Mater. Sci. 2010, 45, 1321.
[25] Verheyde, B.; Dehaen, W. J. Org. Chem. 2001, 66, 4062.
[26] Deng, J.-Y.; Li, Y.; Hu, Z.-Y.; Zhu, M.-X.; Zhu, W.-G. Chin. J. Appl. Chem. 2007, 24, 1119 (in Chinese).
(邓继勇, 刘煜, 胡峥勇, 朱美香, 朱卫国, 应用化学, 2007, 24, 1119.)
[27] Zhu, D.-X.; Lu, H.-F.; Zhang, J.; Zhang, J.-P. CN 101643456, 2009[Chem. Abstr. 2009, 152, 287388].
[28] Wang, G.; Zhang, Z.-Y.; Wei, B.-M.; Zhang, K.-C.; Dai, Z.-Q. Chin. J. Org. Chem. 2008, 28, 538 (in Chinese).
(王刚, 张智勇, 未本美, 张开诚, 戴智群, 有机化学, 2008, 28, 538.)
[29] Bentiss, F.; Lagrenee, M. J. Heterocycl. Chem. 1999, 36, 1029.
[30] Huang, P.; Hu, L.-P.; Shen, D. Chin. J. Liq. Cryst. Disp. 2010, 25, 626 (in Chinese).
(黄佩, 胡兰萍, 沈冬, 液晶与显示, 2010, 25, 626.)

亚甲氧基桥键弯曲型液晶合成与性能研究

Synthesis and Property of Oxymethylene-Bridged Bent-core Liquid Crystals

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