Citation: ZHONG Jin-Lian, PAN Hong, LUO Xu-Zhong, HONG San-Guo, ZHANG Ning, HUANG Jian-Bin. Two-Component Supramolecular Organogels Formed from L-Phenylalanine Derivatives and Aliphatic Amines[J]. Acta Physico-Chimica Sinica, ;2014, 30(9): 1688-1696. doi: 10.3866/PKU.WHXB201407041 shu

Two-Component Supramolecular Organogels Formed from L-Phenylalanine Derivatives and Aliphatic Amines

1.
1. Department of Chemistry, Nanchang University, Nanchang 330031, P. R. China;
2. Key Laboratory of Orgaro-phamaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P. R. China;
3. College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China

Received Date: 31 March 2014
Available Online: 4 July 2014
Fund Project:

A series of monochain L-phenylalanine derivatives were synthesized. L-Phenylalanine derivatives have no gelation abilities, but two-component systems consisting of L-phenylalanine derivatives and aliphatic amines can gelate various organic liquids. The structures of the aggregates in the organogels were investigated using Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) spectroscopy, smallangle X-ray scattering (SAXS), rheological methods, and scanning electron microscopy (SEM). The rheological measurements showed that the steady-state value of the storage elastic modulus (G') was about 10 times larger than that of the loss elastic modulus (G"), indicating that the organogels have od mechanical properties and gel-like characteristics. The SEM, FT-IR, and ¹H NMR results showed that two-component organogels can self-assemble into fibrous or lamellar aggregates in organic liquids through acid-base interactions, intermolecular hydrogen bonding of amide groups, and van der Waals interactions of long alkyl chains. The FT-IR and NMR spectra showed that the hydrogen-bonding and acid-base interactions were the main driving forces for the formation of self-assembled gels. The SAXS results indicated that the gelator molecules assembled into ordered lamellar structures in organic liquids. The ordered lamellar aggregates are juxtaposed and interlocked by van der Waals interactions to form a fibrous superstructure and are finally immobilized in the organic liquid.
- Two-component supramolecular gel,
- L-benzedrine acid derivatives,
- Self-assemble,
- Acid-base interaction,
- Hydrogen bonding
1. [1]
  
  (1) Babu, S. S.; Prasanthkumar, S.; Ajayaghosh, A. Angew. Chem. Int. Edit. 2012, 51, 1766. doi: 10.1002/anie.v51.8
2. [2]
  (2) Chen, X. L.; Liu, K. Q.; He, P. L.; Zhang, H. L.; Fang, Y. Langmuir 2012, 28, 9275. doi: 10.1021/la300856h
3. [3]
  (3) Delbecq, F.; Kaneko, N.; Endo, H.; Kawai, T. J. Colloid Interface Sci. 2012, 384, 94. doi: 10.1016/j.jcis.2012.06.045
4. [4]
  (4) Xin, F. F.; Zhang, H. C.; Hao, B. X.; Sun, T.; Kong, L.; Li, Y. M.; Hou, Y. H.; Li, S. Y.; Zhang, Y.; Hao, A. Y. Colloids and Surfaces A: Physicochem. Eng. Aspects 2012, 410, 18. doi: 10.1016/j.colsurfa.2012.06.008
5. [5]
  (5) Steed, J.W. Chem. Commun. 2011, 47, 1379. doi: 10.1039/c0cc03293j
6. [6]
  (6) Piepenbrock, M. O. M.; Lloyd, G. O.; Clarke, N.; Steed, J.W. Chemical Reviews 2010, 110, 1960. doi: 10.1021/cr9003067
7. [7]
  (7) Abdallah, D. J.;Weiss, R. G. Langmuir 2000, 16, 352. doi: 10.1021/la990795r
8. [8]
  (8) Tsou, C. C.; Sun, S. S. Organic Letters 2006, 8, 387. doi: 10.1021/ol052542x
9. [9]
  (9) Asai, M.; Sugiyasu, K.; Fujita, N.; Shinkai, S. Chemistry Letters 2004, 33, 120. doi: 10.1246/cl.2004.120
10. [10]
  (10) Amdursky, N.; Gazit, E.; Rosenman, G. Advanced Materials 2010, 22, 2311. doi: 10.1002/adma.200904034
11. [11]
  (11) Imato, K.; Nishihara, M.; Kanehara, T.; Amamoto, Y.; Takahara, A.; Otsuka, H. Angew. Chem. Int. Edit. 2012, 51, 1138. doi: 10.1002/anie.201104069
12. [12]
  (12) Zhang, M. M.; Xu, D. H.; Yan, X. Z.; Chen, J. Z.; Dong, S. Y.; Zheng, B.; Huang, F. H. Angew. Chem. Int. Edit. 2012, 124, 7117. doi: 10.1002/ange.201203063
13. [13]
  (13) Luo, X. Z.; Xiao,W.; Li, Z. F;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2009, 329, 372. doi: 10.1016/j.jcis.2008.10.013
14. [14]
  (14) De Loos, M.; Van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem. Int. Edit. 2001, 40, 613. doi: 10.1002/1521-3773(20010202)40:3<>1.0.CO;2-A
15. [15]
  (15) Friggeri, A.; Gronwald, O.; Van Bommel, K. J. C.; Shinkai, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 10754. doi: 10.1021/ja012585i
16. [16]
  (16) Ihara, H.; Sakurai, T.; Yamada, T.; Hashimoto, T.; Takafuji, M.; Sagaura, T.; Hachisako, H. Langmuir 2002, 18, 7120. doi: 10.1021/la025535f
17. [17]
  (17) George, M.;Weiss, R. G. Langmuir 2003, 19, 1017. doi: 10.1021/la026639t
18. [18]
  (18) Hanabusa, K.; Miki, T.; Taguchi, Y.; Koyama, T.; Shirai, H. J. Chem. Soc. Chem. Commun. 1993, 1382.
19. [19]
  (19) Suzuki, M.; Saito, H.; Shirai, H.; Hanabusa, K. New J. Chem. 2007, 31, 1654. doi: 10.1039/b705888h
20. [20]
  (20) Luo, X. Z.; Chen, Z. X.; Xiao,W.; Li, Z. F.;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2011, 362, 113. doi: 10.1016/j.jcis.2011.06.016
21. [21]
  (21) George, M.;Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393. doi: 10.1021/ja016819+
22. [22]
  (22) Luo, X. Z.; Liu, B.; Liang, Y. Q. Chem. Commun. 2001, 1556.
23. [23]
  (23) Partridge, K. S.; Smith, D. K.; Dykes, G. M.; McGrail, P. T. Chem. Commun. 2001, 319.
24. [24]
  (24) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M. Langmuir 2004, 20, 7070. doi: 10.1021/la048751s
25. [25]
  (25) Takahashi, A.; Sakai, M.; Kuto, T. Polym. J. 1980, 12, 335. doi: 10.1295/polymj.12.335
26. [26]
  (26) Luo, X. Z.;Wang, Q.; Zhong, J. L.; Pan, H.; Chen, Z. X. Acta Phys. -Chim. Sin. 2011, 27 (7), 1719. [罗序中, 王琼, 钟金莲, 潘虹, 陈志兴. 物理化学学报, 2011, 27 (7), 1719.] doi: 10.3866/PKU.WHXB20110720
27. [27]
  (27) Luo, X. Z.; Li, Z. F.; Xiao,W.;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2009, 336, 803. doi: 10.1016/j.jcis.2009.04.056
28. [28]
  (28) Van Esch, J. H.; Kelloge, R. H.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281. doi: 10.1016/S0040-4039(96)02292-7
29. [29]
  (29) George, M.; Snyder, S.; Terech, P; Glinka, J.;Weiss, R. G. J. Am. Chem. Soc. 2003, 125, 10275. doi: 10.1021/ja0362407
30. [30]
  (30) Ikeda, S.; Nishinari, K. Food Hydro. 2001, 15, 401. doi: 10.1016/S0268-005X(01)00052-2
31. [31]
  (31) Suzuki, M.; Yumoto, M.; Shirai, H.; Hanabusa, K. Organic & Biomolecular Chemistry 2005, 3, 3073. doi: 10.1039/b507540h
32. [32]
  (32) Huang, X.; Terech, P.; Raghavan, S. R.;Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336. doi: 10.1021/ja0426544
33. [33]
  (33) Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239. doi: 10.1021/la960825f
34. [34]
  (34) Fujimoto, Y.; Ozaki, Y.; Kato, T.; Matsumoto, N.; Iriyama, K. Chem. Phys. Lett. 1992, 196, 347. doi: 10.1016/0009-2614(92)85980-O
35. [35]
  (35) George, S. J.; Ajayaghosh, A. Chem. Eur. J. 2005, 11, 3217.
36. [36]
  (36) Basit, H.; Pal, A.; Sen, S.; Bhattacharya, S. Chem. Eur. J. 2008, 14, 6534. doi: 10.1002/chem.v14:21
37. [37]
  (37) Duncan, D. C.; Whitten, D. G. Langmuir 2000, 16, 6445. doi: 10.1021/la0001631
38. [38]
  (38) Snip, E.; Shinkai, S.; Reinhoudt, D. N. Tetrahedron Lett. 2001, 42, 2153. doi: 10.1016/S0040-4039(01)00095-8
39. [39]
  (39) Abdallah, D. J.; Sirchio, S. A.;Weiss, R. G. Langmuir 2000, 16, 7558. doi: 10.1021/la000730k
40. [40]
  (40) Kunitake, T. Angew. Chem. Int. Edit. 1992, 31, 709.
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