π-共轭三苯基苯衍生物的合成及其胶凝性能

doi:10.3866/PKU.WHXB20110720

物理化学学报 >> 2011, Vol. 27 >> Issue (07): 1719-1724.doi: 10.3866/PKU.WHXB20110720

π-共轭三苯基苯衍生物的合成及其胶凝性能

罗序中, 王琼, 钟金莲, 潘虹, 陈志兴

江西省有机药物化学重点实验室, 赣南师范学院, 江西赣州 341000

收稿日期:2011-01-30 修回日期:2011-05-15 发布日期:2011-06-28
通讯作者: 罗序中 E-mail:Luoxuzhong@yahoo.com.cn
基金资助:
新世纪优秀人才支持计划(NCET-06-0577), 江西省青年科学家培养计划，江西省自然科学基金(2008GZH0012)和江西省研究生创新基金资助项目

Synthesis of π-Conjugated Triphenylbenzene Derivatives and Their Gelling Property

LUO Xu-Zhong, WANG Qiong, ZHONG Jin-Lian, PAN Hong, CHEN Zhi-Xing

Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P. R. China

Received:2011-01-30 Revised:2011-05-15 Published:2011-06-28
Contact: LUO Xu-Zhong E-mail:Luoxuzhong@yahoo.com.cn
Supported by:
The project was supported by the Program for New Century Excellent Talents in Universities, China, (NCET-06-0577), Young Scientists Training Plan of Jiangxi Province, China, Natural Science Foundation of Jiangxi Province, China (2008GZH0012), and Graduate Innovation Fund of Jiangxi Province, China.

摘要/Abstract

摘要：

合成了一系列三单脂肪链具有盘状结构的三苯基苯衍生物并研究了其在有机溶剂中自组装行为. 结果表明, 该系列衍生物在多种低极性有机溶剂中可以形成稳定的凝胶, 利用小角X射线衍射实验和扫描电子显微镜技术观察到干凝胶的分子排列具有层状结构, 形成纤维状和片层状聚集, 紫外-可见吸收光谱和红外光谱结果表明分子间氢键和π-π共轭堆积效应是形成自组装凝胶的主要驱动力. 在形成凝胶过程中, 凝胶剂分子在溶液中通过盘状中心的π-π共轭堆积效应和酰胺键的分子间氢键作用自组装成层状结构, 层状结构进一步组装形成纤维状和片层状聚集体, 最终形成三维网状结构阻碍溶剂流动形成凝胶.

关键词: 有机凝胶剂, 三苯基苯衍生物, 自组装, 氢键

Abstract:

A series of discotic molecules containing triphenylbenzene group and three monochains were synthesized and their self-assembly properties were studied. These derivatives formed stable gels in many low polarity organic solvents. The lamellar and fibrous aggregate morphologies of the xerogels and the layered structure of the gel aggregates were studied by scanning electron microscopy (SEM) and small angle X-ray diffraction (SA-XRD), respectively. Fourier transform infrared (FT-IR) spectroscopy and UV-Vis absorption spectroscopy revealed that the hydrogen bonding and π-π interactions were the main driving force for the formation of a self-assembled gel. During gel formation, the gelator molecules self-assemble into ordered lamellar aggregates in organic solvents through a π-π conjugation stacking effect and hydrogen bonding. The ordered lamellar aggregates are juxtaposed and interlocked by van der Waals interactions to form sheet-like structure or fiber superstructure and finally immobilize into the organic liquids.

Key words: Organic gelator, Triphylbenzene deivative, Self-assembly, Hydrogen bond

MSC2000:

O648

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罗序中, 王琼, 钟金莲, 潘虹, 陈志兴. π-共轭三苯基苯衍生物的合成及其胶凝性能[J]. 物理化学学报, 2011, 27(07): 1719-1724.

LUO Xu-Zhong, WANG Qiong, ZHONG Jin-Lian, PAN Hong, CHEN Zhi-Xing. Synthesis of π-Conjugated Triphenylbenzene Derivatives and Their Gelling Property[J]. Acta Phys. -Chim. Sin., 2011, 27(07): 1719-1724.

参考文献

(1) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821.
(2) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4329.
(3) Wong, G. C. L.; Tang, J. X.; Lin, A.; Li, Y.; Janmey, P. A.; Safinya, C. R. Science 2000, 288, 2035.
(4) Hwang, I.; Jeon,W. S.; Kim, H. J.; Kim, D.; Kim, H.; Selvapalam, N.; Fujita, N.; Shinkai, S.; Kim, K. Angew. Chem. Int. Edit. 2007, 46, 210.
(5) Bhogala, B. R.; Captain, B.; Parthasarathy, A.; Ramamurthy, V. J. Am. Chem. Soc. 2010, 132, 13434.
(6) Shen, L. Y.; Chen, X. Z.; Yu, H. T.; Liang, G. Chin. J. Org. Chem. 2009, 29 (3), 321. [沈利英, 陈肖卓, 于海涛, 梁刚. 有机化学, 2009, 29 (3), 321.]
(7) Bommel, K. J. C. V.; Pol, C. V. D.; Muizebelt, I.; Friggeri, A.; Heeres, A.; Meetsma, A.; Feringa, B. L.; Esch, J.V. Angew. Chem. Int. Edit. 2004, 43, 1663.
(8) Gestel, J. V.; Palmans, A. R. A.; Titulaer, B.; Vekemans, J. A. J. M.; Meijer, E.W. J. Am. Chem. Soc. 2005, 127, 5490.
(9) Bao, C. Y.; Lu, R.; Xue, P. C.; Jin, M.; Tan, C. H.; Xu, T. H.; Liu, G. F.; Zhao, Y. Y. Chem. Eur. J. 2006, 12, 3287.
(10) Elmorsyfa, S. S.; Pelter, B.; Smtthb, K. Tetrahedron Lett. 1991, 32 (33), 4175.
(11) Luo, X. Z.; Li, Z. F.; Xiao,W.;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2009, 336, 803.
(12) Huang, X. T.; Erech, P.; Raghavan, S. R.;Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336.
(13) Jung, J.; Ono, Y.; Shinkai, S. Angew. Chem. Int. Edit. 2000, 39, 1862.
(14) Liang, Y. Q.; Jiang, Y. T.; Tian, Y. C. Acta Phys. -Chim. Sin. 1991, 7 (1), 72. [梁映秋, 姜玉涛, 田永池. 物理化学学报, 1991, 7 (1), 72.]
(15) Fujimoto, Y.; Ozaki, Y.; Kato, T.; Matsumoto, N.; Iriyama, K. Chem. Phys. Lett. 1992, 196, 347.
(16) Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239.
(17) Kunitake, T. Angew. Chem. Int. Edit. 1992, 31, 709.
(18) Shitakawa, M.; Kawano, S.; Fujita, N.; Sada, K.; Shinkai, S. J. Org. Chem. 2003, 68, 5037.
(19) Kadam, J.; Faul, C. F. J.; Scherf, U. Chem. Mater. 2004, 16, 3867.
(20) Jung, J. H.; John, G.; Yoshida, K.; Shimizu, T. J. Am. Chem. Soc. 2002, 124, 10674.
(21) Jung, J. H.; Shinkai, S.; Shimizu, T. Chem. Eur. J. 2002, 8, 2684.
(22) Otsumi, E.; Kamaras, P.;Weiss, R. G. Angew. Chem. Int. Edit. 1996, 35, 1324.

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π-共轭三苯基苯衍生物的合成及其胶凝性能

Synthesis of π-Conjugated Triphenylbenzene Derivatives and Their Gelling Property

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