Citation: 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 Physico-Chimica Sinica, ;2011, 27(07): 1719-1724. doi: 10.3866/PKU.WHXB20110720 shu

Synthesis of π-Conjugated Triphenylbenzene Derivatives and Their Gelling Property

1.
Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P. R. China

Received Date: 30 January 2011
Available Online: 26 May 2011
Fund Project: 新世纪优秀人才支持计划(NCET-06-0577) (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) (2008GZH0012)

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.
- Organic gelator,
- Triphylbenzene deivative,
- Self-assembly,
- Hydrogen bond
1. [1]
  
  (1) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821.
2. [2]
  (2) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4329.
3. [3]
  (3) Wong, G. C. L.; Tang, J. X.; Lin, A.; Li, Y.; Janmey, P. A.; Safinya, C. R. Science 2000, 288, 2035.
4. [4]
  (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. [5]
  (5) Bhogala, B. R.; Captain, B.; Parthasarathy, A.; Ramamurthy, V. J. Am. Chem. Soc. 2010, 132, 13434.
6. [6]
  (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. [7]
  (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. [8]
  (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. [9]
  (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. [10]
  (10) Elmorsyfa, S. S.; Pelter, B.; Smtthb, K. Tetrahedron Lett. 1991, 32 (33), 4175.
11. [11]
  (11) Luo, X. Z.; Li, Z. F.; Xiao,W.;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2009, 336, 803.
12. [12]
  (12) Huang, X. T.; Erech, P.; Raghavan, S. R.;Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336.
13. [13]
  (13) Jung, J.; Ono, Y.; Shinkai, S. Angew. Chem. Int. Edit. 2000, 39, 1862.
14. [14]
  (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. [15]
  (15) Fujimoto, Y.; Ozaki, Y.; Kato, T.; Matsumoto, N.; Iriyama, K. Chem. Phys. Lett. 1992, 196, 347.
16. [16]
  (16) Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239.
17. [17]
  (17) Kunitake, T. Angew. Chem. Int. Edit. 1992, 31, 709.
18. [18]
  (18) Shitakawa, M.; Kawano, S.; Fujita, N.; Sada, K.; Shinkai, S. J. Org. Chem. 2003, 68, 5037.
19. [19]
  (19) Kadam, J.; Faul, C. F. J.; Scherf, U. Chem. Mater. 2004, 16, 3867.
20. [20]
  (20) Jung, J. H.; John, G.; Yoshida, K.; Shimizu, T. J. Am. Chem. Soc. 2002, 124, 10674.
21. [21]
  (21) Jung, J. H.; Shinkai, S.; Shimizu, T. Chem. Eur. J. 2002, 8, 2684.
22. [22]
  (22) Otsumi, E.; Kamaras, P.;Weiss, R. G. Angew. Chem. Int. Edit. 1996, 35, 1324.
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沈阳化工大学材料科学与工程学院沈阳 110142