Light-controlled formation of vesicles and supramolecular organogels by a cholesterol-bearing amphiphilic molecular switch

Chemistry - A European Journal

Volumn 20, Issue 6, 2014, Pages 1737-1742

  Van Herpt, Jochem T ^a   Areephong, Jetsuda ^a   Stuart, Marc C A ^a   Browne, Wesley R ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

gels; molecular switches; photochromism; supramolecular chemistry; vesicles

Indexed keywords

CHOLESTEROL; MACROGOL DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE; SURFACTANT;

ARTICLE; CHEMISTRY; GEL; LIGHT; MOLECULAR SWITCHES; PHOTOCHROMISM; SUPRAMOLECULAR CHEMISTRY; VESICLES;

GELS; MOLECULAR SWITCHES; PHOTOCHROMISM; SUPRAMOLECULAR CHEMISTRY; VESICLES;

CHOLESTEROL; GELS; LIGHT; POLYETHYLENE GLYCOLS; PYRIDINES; SURFACE-ACTIVE AGENTS;

EID: 84895057669     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302902     Document Type: Article

References (51)

1. X. Zhang, C. Wang, Chem. Soc. Rev. 2011, 40, 94-101
2. J. M. Zayed, N. Nouvel, U. Rauwald, O. A. Scherman, Chem. Soc. Rev. 2010, 39, 2806-2816
3. Q. Chen, Y. Feng, D. Zhang, G. Zhang, Q. Fan, S. Sun, D. Zhu, Adv. Funct. Mater. 2010, 20, 36-42.
4. M. Hasegawa, M. Iyoda, Chem. Soc. Rev. 2010, 39, 2420-2427.
5. A. C. Coleman, J. M. Beierle, M. C. A. Stuart, B. Macia, G. Caroli, J. T. Mika, D. J. Van Dijken, J. Chen, W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2011, 6, 547-552
6. J. P. Hill, W. S. Jin, A. Kosaka, T. Fukushima, H. Ichihara, T. Shimomura, K. Ito, T. Hashizume, N. Ishii, T. Aida, Science 2004, 304, 1481-1483.
7. A. J. Dzieciol, S. Mann, Chem. Soc. Rev. 2012, 41, 79-85.
8. Y. Zhao, J. Mater. Chem. 2009, 19, 4887-4895.
9. X. Yang, G. Zhang, D. Zhang, J. Mater. Chem. 2012, 22, 38-50
10. J. H. van Esch, B. L. Feringa, Angew. Chem. 2000, 112, 2351-2354
11. Angew. Chem. Int. Ed. 2000, 39, 2263-2266
12. M. De Loos, B. L. Feringa, J. H. Van Esch, Eur. J. Org. Chem. 2005, 3615-3631
13. Molecular Gels, Materials with Self-Assembled Fibrillar Networks (Eds.:, R. G. Weiss, P. Terech,), Springer, Dordrecht 2005.
14. M. C. Branco, J. P. Schneider, Acta Biomater. 2009, 5, 817-831.
15. G. D. Nicodemus, S. J. Bryant, Tissue Eng. 2008, 14, 149-165.
16. K. Ariga, H. Ito, J. P. Hill, H. Tsukube, Chem. Soc. Rev. 2012, 41, 5800-5835.
17. T. Fenske, H. Korth, A. Mohr, C. Schmuck, Chem. Eur. J. 2012, 18, 738-755
18. N. Fomina, J. Sankaranarayanan, A. Almutairi, Adv. Drug Delivery Rev. 2012, 64, 1005-1020
19. E. Fleige, M. A. Quadir, R. Haag, Adv. Drug Delivery Rev. 2012, 64, 866-884.
20. I. Tomatsu, K. Peng, A. Kros, Adv. Drug Delivery Rev. 2011, 63, 1257-1266.
21. B. L. Feringa, W. R. Browne, Molecular Switches, Vol. 1, Wiley-VCH, Weinheim, Germany, 2011
22. M. Irie, M. Mohri, J. Org. Chem. 1988, 53, 803-808
23. K. Matsuda, M. Irie, J. Photochem. Photobiol. C 2004, 5, 169-182
24. A. J. Myles, N. R. Branda, Adv. Funct. Mater. 2002, 12, 167-173.
25. T. Hirose, K. Matsuda, M. Irie, J. Org. Chem. 2006, 71, 7499-7508
26. X. Zhou, Y. Duan, S. Yan, Z. Liu, C. Zhang, L. Yao, C. Guanglei, Chem. Commun. 2011, 47, 6876-6878.
27. Y. He, Y. Yamamoto, W. Jin, T. Fukushima, A. Saeki, S. Seki, N. Ishii, T. Aida, Adv. Mater. 2010, 22, 829-832.
28. J. Liang, J. Yin, Z. Li, C. Zhang, D. Wu, S. H. Liu, Dyes Pigm. 2011, 91, 364-369
29. R. T. F. Jukes, V. Adamo, F. Hartle, P. Belser, L. De Cola, Inorg. Chem. 2004, 43, 2779-2792.
30. K. Uchida, Y. Yamanoi, T. Yonezawa, H. Nishihara, J. Am. Chem. Soc. 2011, 133, 9239-9241
31. A. Uyama, S. Yamazoe, S. Shigematsu, M. Morimoto, S. Yokojima, H. Mayama, Y. Kojima, S. Nakamura, K. Uchida, Langmuir 2011, 27, 6395-6400
32. K. Uchida, N. Nishikawa, N. Izumi, S. Yamazoe, H. Mayama, Y. Kojima, S. Yokojima, S. Nakamura, K. Tsujii, M. Irie, Angew. Chem. 2010, 122, 6078-6080
33. Angew. Chem. Int. Ed. 2010, 49, 5942-5944.
34. J. J. D. De Jong, L. N. Lucas, R. M. Kellogg, J. H. van Esch, B. L. Feringa, Science 2004, 304, 278-281.
35. Z. Chen, Y. He, Y. Wang, X. Wang, Macromol. Rapid Commun. 2011, 32, 977-982
36. M. Takeshita, M. Hayashi, K. Souichi, K. H. Mohammed, T. Yamato, Chem. Commun. 2005, 761-763.
37. C. Denekamp, B. L. Feringa, Adv. Mater. 1998, 10, 1080-1082
38. T. Van Leeuwen, T. C. Pijper, J. Areephong, B. L. Feringa, W. R. Browne, N. Katsonis, J. Mater. Chem. 2011, 21, 3142-3146.
39. Y. Wang, P. Han, H. Xu, Z. Wang, X. Zhang, A. V. Kabanov, Langmuir 2010, 26, 709-715
40. Q. Jin, C. Luy, J. Ji, S. Argawal, J. Polym. Sci. Part A 2012, 50, 451-457
41. A. Matsumura, K. Tsuchiya, K. Torigoe, K. Sakai, H. Sakai, M. Abe, Langmuir 2011, 27, 1610-1617.
42. J. Eastoe, M. Sanchez-Dominguez, P. Wyatt, R. K. Heenan, Chem. Commun. 2004, 2608-2609
43. N. Koumura, M. Kudo, N. Tamaoki, Langmuir 2004, 20, 9897-9900.
44. E. Fischer, J. Phys. Chem. 1967, 71, 3704-3706.
45. S. Xiao, Y. Zou, J. Wu, Y. Zhou, T. Yi, F. Li, C. Huang, J. Mater. Chem. 2007, 17, 2483-2489
46. Y. Zou, T. Yi, S. Xiao, F. Li, C. Li, X. Gao, J. Wu, M. Yu, C. Huang, J. Am. Chem. Soc. 2008, 130, 15750-15751.
47. Y. Lin, R. G. Weiss, Macromolecules 1987, 20, 414-417.
48. J. A. Allen, R. A. Halverson-Tamboli, M. M. Rasenick, Nat. Rev. Neurosci. 2007, 8, 128-140
49. Z. Korade, A. K. Kenworthy, Neuropharmacology 2008, 55, 1265-1273.
50. M. M. Kamal, D. Mills, M. Grzybek, J. Howard, Proc. Natl. Acad. Sci. USA 2009, 106, 22245-22250
51. H. T. Jung, B. Coldren, J. A. Zasaszinski, D. J. Iampietro, E. W. Kaler, Proc. Natl. Acad. Sci. USA 2001, 98, 1353-1357.