Citation: HE You-Zhou, LIU Yun, LIU Peng, FENG Wen, YUAN Li-Hua. Self-Assembly of Vesicles from Oli aramide Based on Multiple Hydrogen Bonds[J]. Acta Physico-Chimica Sinica, ;2014, 30(8): 1501-1508. doi: 10.3866/PKU.WHXB201406122 shu

Self-Assembly of Vesicles from Oli aramide Based on Multiple Hydrogen Bonds

1.
Key Laboratory for Radiation Physics and Technology of the Ministry of Education, Institute of Nuclear Science and Technology, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China

Received Date: 17 April 2014
Available Online: 12 June 2014
Fund Project:

Six-hydrogen-bonded oli aramide heteroduplexes demonstrate extremely high sequencespecificity and tunable stability during their self-assembly. The self-assembly behavior of molecular oli aramide 1 arrayed in a DADDAD-DADDAD sequence and that in the presence of oli aramide 2 with an ADAADAADAADA sequence were examined using multiple techniques, including scanning electron microscopy (SEM), transmission electron microscopy (TEM), and dynamic light scattering (DLS). Results from these experiments indicate that 1 can self-assemble to vesicles with uniform shapes in both tetrahydrofuran/methanol (V/V, 85/15) and acetone, the size of which increased with an increase in solution concentration. Upon addition of the corresponding complementary 2, the vesicles turned into solid balls. Fluorescence microscopy experiments revealed that the vesicles were able to encapsulate the fluorescence molecules (Rhodamine B). With further modification of molecular structures, these vesicles may hold potential for applications as drug carrier as well as in controlled-release technology.
- Self-assembly,
- Vesicle,
- Oli aramide,
- Hydrogen bond,
- Molecular duplex
1. [1]
  
  (1) Graff, A.; Sauer, M.; Gelder, P. V.; Meier,W. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5064. doi: 10.1073/pnas.062654499
2. [2]
  (2) Stoenescu, R.; Meier,W. Chem. Commun. 2002, 3016.
3. [3]
  (3) Wang, Y. Y.; Hua,W.; Liu, T. Q. Acta Phys. -Chim. Sin. 2011, 27, 1907. [王元有, 华伟, 刘天晴. 物理化学学报, 2011, 27, 1907.] doi: 10.3866/PKU.WHXB20110822
4. [4]
  (4) Stanish, I.; Lowy, D. A.; Hung, C.W.; Singh, A. Adv. Mater. 2005, 17, 1194.
5. [5]
  (5) Yan, Q.; Yuan, J. Y.; Cai, Z. N.; Xin, Y.; Kang, Y.; Yin, Y.W. J. Am. Chem. Soc. 2010, 132, 9268. doi: 10.1021/ja1027502
6. [6]
  (6) Yan, Q.; Zhou, R.; Fu, C. K.; Zhang, H. J.; Yin, Y.W.; Yuan, J. Y. Angew. Chem., Int. Edit. 2011, 50, 4923. doi: 10.1002/anie.v50.21
7. [7]
  (7) Discher, D. E.; Eisenberg, A. Science 2002, 297, 967. doi: 10.1126/science.1074972
8. [8]
  (8) Jones, R. A. L. Nat. Mater. 2004, 3, 209. doi: 10.1038/nmat1109
9. [9]
  (9) Duan, Q. P.; Cao, Y.; Li, Y.; Hu, X. Y.; Xiao, T. X.; Lin, C.; Pan, Y.;Wang, L. Y. J. Am. Chem. Soc. 2013, 135, 10542. doi: 10.1021/ja405014r
10. [10]
  (10) Li, S.; Qiu, Y. Q.; Zhang, S. H.; Gao, Y. H. Acta Phys. -Chim. Sin. 2011, 27, 2167. [李爽, 邱玉琴, 张锁慧, 高云华. 物理化学学报, 2011, 27, 2167.] doi: 10.3866/PKU.WHXB20110833
11. [11]
  (11) Menger, F. M.; Gabrielson, K. D. Angew. Chem. Int. Edit. 1995, 34, 2091.
12. [12]
  (12) Moss, R. A.; Bizzi tti, G. O. J. Am. Chem. Soc. 1981, 103, 6512. doi: 10.1021/ja00411a049
13. [13]
  (13) Zhao, G. X.; Huang, J. B. Acta Phys. -Chim. Sin. 1992, 8, 583. [赵国玺, 黄建滨. 物理化学学报, 1992, 8, 583.] doi: 10.3866/PKU.WHXB19920503
14. [14]
  (14) Discher, B. M.;Won, Y. Y.; Ege, D. S.; Lee, J. C. M.; Bates, F. S.; Discher, D. E.; Hammer, D. A. Science 1999, 284, 1143. doi: 10.1126/science.284.5417.1143
15. [15]
  (15) Lee, M.; Lee, S. J.; Jiang, L. H. J. Am. Chem. Soc. 2004, 126, 12724. doi: 10.1021/ja045918v
16. [16]
  (16) Guan, B.; Jiang, M.; Yang, X.; Liang, Q.; Chen, Y. Soft Matter 2008, 4, 1393. doi: 10.1039/b805312j
17. [17]
  (17) Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267. doi: 10.1039/b603088m
18. [18]
  (18) Ravoo, B. J.; Darcy, R. Angew. Chem. Int. Edit. 2000, 39, 4324.
19. [19]
  (19) Lim, C.W.; Crespo-Biel, O.; Stuart, M. C. A.; Reinhoudt, D. N.; Huskens, J.; Ravoo, B. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 6986. doi: 10.1073/pnas.0611123104
20. [20]
  (20) Zhang, K. D.; Zhou, T. Y.; Zhao, X.; Jiang, X. K.; Li, Z. T. Langmuir 2012, 28, 14839.
21. [21]
  (21) Xu, Y. X.;Wang, G. T.; Zhao, X.; Jiang, X. K.; Li, Z. T. Langmuir 2009, 25, 2684. doi: 10.1021/la8034243
22. [22]
  (22) Xu, Y. X.;Wang, G. T.; Zhao, X.; Jiang, X. K.; Li, Z. T. Soft Matter 2010, 6, 1246. doi: 10.1039/b917576h
23. [23]
  (23) Du, P.;Wang, G. T.; Zhao, X.; Li, G. Y.; Jiang, X. K.; Li, Z. T. Tetrahedron Lett. 2010, 51, 188. doi: 10.1016/j.tetlet.2009.10.115
24. [24]
  (24) ng, B. Accounts Chem. Res. 2012, 45, 2077. doi: 10.1021/ar300007k
25. [25]
  (25) Li, M. F.; Yamato, K.; Ferguson, J. S.; ng, B. J. Am. Chem. Soc. 2006, 128, 12628. doi: 10.1021/ja064515n
26. [26]
  (26) Li, M. F.; Yamato, K.; Ferguson, J. S.; Singarapu, K. K.; Szyperski, T.; ng, B. J. Am. Chem. Soc. 2008, 130, 491. doi: 10.1021/ja072567m
27. [27]
  (27) Yuan, L. H.; Zhang, P. H.; Feng,W.; ng, B. Curr. Org. Chem. 2011, 15, 1250. doi: 10.2174/138527211795378236
28. [28]
  (28) Yang, X.W.; Hua, F. J.; Yamato, K.; Ruckenstein, E.; ng, B.; Kim,W.; Ryu, C. Y. Angew. Chem. Int. Edit. 2004, 43, 6471.
29. [29]
  (29) Yang, X.W.; ng, B. Angew. Chem. Int. Edit. 2005, 44, 1352.
30. [30]
  (30) Cao, R. K.; Zhou, J. J.;Wang,W.; Feng,W.; Li, X. H.; Zhang, P. H.; Deng, P. C.; Yuan, L. H.; ng, B. Org. Lett. 2010, 12, 2958. doi: 10.1021/ol100953e
31. [31]
  (31) Zhang, P. H.; Chu, H. Z.; Li, X. H.; Feng,W.; Deng, P. C.; Yuan, L. H.; ng, B. Org. Lett. 2011, 13, 54. doi: 10.1021/ol102522m
32. [32]
  (32) Zeng, J. S.;Wang,W.; Deng, P. C.; Feng,W.; Zhou, J. J.; Yang, Y. Y.; Yuan, L. H.; Yamato, K.; ng, B. Org. Lett. 2011, 13, 3798. doi: 10.1021/ol201282d
33. [33]
  (33) Pan, X. S.; Chen, C.; Peng, J.; Yang, Y. A.;Wang, Y. H.; Feng, W.; Deng, P. C.; Yuan, L. H. Chem. Commun. 2012, 48, 9510. doi: 10.1039/c2cc35004a
34. [34]
  (34) Li, X. H.; Fang, Y. Y.; Deng, P. C.; Hu, J. C.; Li, T.; Feng,W.; Yuan, L. H. Org. Lett. 2011, 13, 4628. doi: 10.1021/ol2018455
35. [35]
  (35) Li, X. H.; Jia, Y. M.; Ren, Y.;Wang, Y. J.; Hu, J. C.; Ma, T.; Feng,W.; Yuan, L. H. Org. Biomol. Chem. 2013, 11, 6975. doi: 10.1039/c3ob40998h
36. [36]
  (36) Liu, Y.; He, Y. Z.; Yuan, L. H.; Feng,W. Acta Phys. -Chim. Sin. 2011, 27, 918. [刘云, 贺有周, 袁立华, 冯文. 物理化学学报, 2011, 27, 918.] doi: 10.3866/PKU.WHXB20110403
37. [37]
  (37) Jin, Y. D.; Liu, Y.; Yang, Y. A.; Zhang, D.; Dan, G. P.; Du, J.; Yuan, L. H.; Feng,W. Chin. J. Org. Chem. 2011, 31, 1864. [金永东, 刘云, 杨永安, 张东, 但贵萍, 杜鹃, 袁立华, 冯文. 有机化学, 2011, 31, 1864.]
38. [38]
  (38) Zeng, H. Q.; Miller, R. S.; Flowers, R. A.; ng, B. J. Am. Chem. Soc. 2000, 122, 2635. doi: 10.1021/ja9942742
39. [39]
  (39) Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J. L.; Oitker, R.; Yen, M.; Zhao, J. C.; Zang, L. J. Am. Chem. Soc. 2006, 128, 7390. doi: 10.1021/ja061810z
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