Heat-induced morphological transformation of supramolecular nanostructures by retro-Diels-Alder reaction

Chemistry - A European Journal

Volumn 18, Issue 41, 2012, Pages 13091-13096

  Ikeda, Masato ^a,d   Ochi, Rika ^a   Kurita, Yu Shi ^a   Pochan, Darrin J ^c   Hamachi, Itaru ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF DELAWARE   (United States)

^d GIFU UNIVERSITY   (Japan)

Author keywords

amphiphiles; gels; nanostructures; self assembly; supamolecular chemistry

Indexed keywords

BOLAAMPHIPHILES; EXTERNAL STIMULUS; MOLECULAR ASSEMBLY; MOLECULAR CONVERSION; MORPHOLOGICAL TRANSFORMATIONS; RETRO-DIELS-ALDER REACTIONS; SOFT MATERIAL; SUPRA-MOLECULAR NANO STRUCTURES; SUPRAMOLECULAR HYDROGELS; SUPRAMOLECULAR SYSTEMS;

AMPHIPHILES; GELS; HYDROGELS; NANOFIBERS; NANOSHEETS; NANOSTRUCTURES; REACTION KINETICS; SELF ASSEMBLY; THERMODYNAMICS;

SUPRAMOLECULAR CHEMISTRY;

EID: 84867062044     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201670     Document Type: Article

References (96)

1. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995.
2. J. S. Lindsey, New J. Chem. 1991, 15, 153-180.
3. G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319.
4. G. John, J. H. Jung, H. Minamikawa, K. Yoshida, T. Shimizu, Chem. Eur. J. 2002, 8, 5494-5500
5. M. Shirakawa, N. Fujita, S. Shinkai, J. Am. Chem. Soc. 2003, 125, 9902-9903
6. M. Reches, E. Gazit, Nano Lett. 2004, 4, 581-585
7. P. Jonkheijm, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83
8. T. Yamamoto, T. Fukushima, Y. Yamamoto, A. Kosaka, W. Jin, N. Ishii, T. Aida, J. Am. Chem. Soc. 2006, 128, 14337-14340
9. X. Yan, Q. He, K. Wang, L. Duan, Y. Cui, J. Li, Angew. Chem. 2007, 119, 2483-2486
10. X. Zhang, Z. Chen, F. Würthner, J. Am. Chem. Soc. 2007, 129, 4886-4887
11. A. Ajayaghosh, P. Chithra, R. Varghese, Angew. Chem. 2007, 119, 234-237
12. Angew. Chem. Int. Ed. 2007, 46, 230-233
13. J. Baram, E. Shirman, N. Ben-Shitrit, A. Ustinov, H. Weissman, I. Pinkas, S. G. Wolf, B. Rybtchinski, J. Am. Chem. Soc. 2008, 130, 14966-14967
14. H. Shao, J. R. Parquette, Angew. Chem. 2009, 121, 2563-2566
15. Angew. Chem. Int. Ed. 2009, 48, 2525-2528
16. S. Yagai, S. Kubota, H. Saito, K. Unoike, T. Karatsu, A. Kitamura, A. Ajayaghosh, M. Kanesato, Y. Kikkawa, J. Am. Chem. Soc. 2009, 131, 5408-5410
17. E. T. Pashuck, S. I. Stupp, J. Am. Chem. Soc. 2010, 132, 8819-8821
18. P. Beseniusa, G. Portaleb, P. H. H. Bomansc, H. M. Janssend, A. R. A. Palmansa, E. W. Meijer, Proc. Natl. Acad. Sci. USA 2010, 107, 17888-17893
19. L. Ziserman, H.-Y. Lee, S. R. Raghavan, A. Mor, D. Danino, J. Am. Chem. Soc. 2011, 133, 2511-2517
20. A. C. Coleman, J. M. Beierle, M. C. A. Stuart, B. Maciá, G. Caroli, J. T. Mika, D. J. van Dijken, J. Chen, W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2011, 6, 547-552
21. J. W. Sadownik, J. Leckie, R. V. Ulijn, Chem. Commun. 2011, 47, 728-730
22. D. Ke, C. Zhan, A. D. Q. Li, J. Yao, Angew. Chem. 2011, 123, 3799-3803
23. Angew. Chem. Int. Ed. 2011, 50, 3715-3719.
24. S. Zhang, T. C. Holmes, C. M. DiPersio, R. O. Hynes, X. Su, A. Rich, Biomaterials 1995, 16, 1385-1393
25. T. C. Holmes, S. de Lacalle, X. Su, G. Liu, A. Rich, S. Zhang, Proc. Natl. Acad. Sci. USA 2000, 97, 6728-6733
26. G. A. Silva, C. Czeisler, K. L. Niece, E. Beniach, D. A. Harrington, J. A. Kessler, S. I. Stupp, Science 2004, 303, 1352-1355
27. V. Jayawarna, M. Ali, T. A. Jowitt, A. F. Miller, A. Saiani, J. E. Gough, R. V. Ulijn, Adv. Mater. 2006, 18, 611-614
28. A. Mahler, M. Reches, M. Rechter, S. Cohen, E. Gazit, Adv. Mater. 2006, 18, 1365-1370
29. F. Gelain, A. Horii, S. Zhang, Macromol. Biosci. 2007, 7, 544-551 and references cited therein
30. L. Haines-Butterick, K. Rajogopal, M. Branco, D. Salick, R. Rughani, M. Pilarz, M. S. Lamm, D. J. Pochan, J. P. Schneider, Proc. Natl. Acad. Sci. USA 2007, 104, 7791-7796
31. M. Ikeda, S. Ueno, S. Matsumoto, Y. Shimizu, H. Komatsu, K.-i. Kusumoto, I. Hamachi, Chem. Eur. J. 2008, 14, 10808-10815
32. Y. Kumada, N. A. Hammonda, S. Zhang, Soft Matter 2010, 6, 5073-5079
33. Y. Tsuda, Y. Morimoto, S. Takeuchi, Langmuir 2010, 26, 2645-2649
34. E. L. Bakota, Y. Wang, F. R. Danesh, J. D. Hartgerink, Biomacromolecules 2011, 12, 1651-1657.
35. K. J. C. van Bommel, M. C. A. Stuart, B. L. Feringa, J. van Esch, Org. Biomol. Chem. 2005, 3, 2917-2920
36. N. Sreenivasachary, J.-M. Lehn, Chem. Asian J. 2008, 3, 134-139
37. P. K. Vemula, G. A. Cruikshank, J. M. Karp, G. John, Biomaterials 2009, 30, 383-393
38. M. C. Branco, D. J. Pochan, N. J. Wagner, J. P. Schneider, Biomaterials 2009, 30, 1339-1347
39. G. Liang, Z. Yang, R. Zhang, L. Li, Y. Fan, Y. Kuang, Y. Gao, T. Wang, W. W. Lu, B. Xu, Langmuir 2009, 25, 8419-8422
40. S. Koutsopoulos, L. D. Unsworth, Y. Nagai, S. Zhang, Proc. Natl. Acad. Sci. USA 2009, 106, 4623-4628
41. M. Ikeda, R. Ochi, A. Wada, I. Hamachi, Chem. Sci. 2010, 1, 491-498
42. X. Li, J. Li, Y. Gao, Y. Kuang, J. Shi, B. Xu, J. Am. Chem. Soc. 2010, 132, 17707-17709
43. J. Sáez, B. Escuder, J. F. Miravet, Tetrahedron 2010, 66, 2614-2618.
44. D. J. Pochan, J. P. Schneider, J. Kretsinger, B. Ozbaas, K. Rajagopal, L. Haines, J. Am. Chem. Soc. 2003, 125, 11802-11803
45. K.-S. Moon, H.-J. Kim, E. Lee, M. Lee, Angew. Chem. 2007, 119, 6931-6934
46. Angew. Chem. Int. Ed. 2007, 46, 6807-6810
47. Z. Chu, Y. Feng, Chem. Commun. 2011, 47, 7191-7193
48. Z. Huang, H. Lee, E. Lee, S.-K. Kang, J.-M. Nam, M. Lee, Nat. Commun. 2011, 2, 459.
49. K. Kuroiwa, T. Shibata, A. Takada, N. Nemoto, N. Kimizuka, J. Am. Chem. Soc. 2004, 126, 2016-2021
50. J.-L. Zhou, X.-J. Chenand, Y.-S. Zheng, Chem. Commun. 2007, 5200-5202
51. Y. Li, J. Liu, G. Du, H. Yan, H. Wang, H. Zhang, W. An, W. Zhao, T. Sun, F. Xin, L. Kong, Y. Li, A. Hao, J. Hao, J. Phys. Chem. B 2010, 114, 10321-10326
52. X. de Hatten, N. Bell, N. Yufa, G. Christmann, J. R. Nitschke, J. Am. Chem. Soc. 2011, 133, 3158-3164.
53. As a review, see:, P.-E. Hellberg, K. Bergström, K. Holmberg, J. Surfactants Deterg. 2000, 3, 81-91.
54. L. A. Haines, K. Rajagopal, B. Ozbas, D. A. Salick, D. J. Pochan, J. P. Schneider, J. Am. Chem. Soc. 2005, 127, 17025-17029
55. T. Muraoka, C.-Y. Koh, H. Cui, S. I. Stupp, Angew. Chem. 2009, 121, 6060-6063
56. Angew. Chem. Int. Ed. 2009, 48, 5946-5949. Very recently, a unique photoresponsive supramolecular hydrogel was reported; see
57. J. Li, J. M. A. Carnall, M. C. A. Stuart, S. Otto, Angew. Chem. 2011, 123, 8534-8536
58. Angew. Chem. Int. Ed. 2011, 50, 8384-8386.
59. Y. Zhang, H. Gu, Z. Yang, B. Xu, J. Am. Chem. Soc. 2003, 125, 13680-13681
60. H.-W. Jun, V. Yuwono, S. E. Paramonov, J. D. Hartgerink, Adv. Mater. 2005, 17, 2612-2617
61. R. V. Ulijn, J. Mater. Chem. 2006, 16, 2217-2225
62. P. K. Vemula, J. Li, G. John, J. Am. Chem. Soc. 2006, 128, 8932-8938
63. R. J. Williams, A. M. Smith, R. Collins, N. Hodson, A. K. Das, R. V. Ulijn, Nat. Nanotechnol. 2009, 4, 19-24
64. Y. Gao, Y. Kuang, Z.-F. Guo, Z. Guo, I. J. Krauss, B. Xu, J. Am. Chem. Soc. 2009, 131, 13576-13577
65. D. Koda, T. Maruyama, N. Minakuchi, K. Nakashima, M. Goto, Chem. Commun. 2010, 46, 979-981
66. M. J. Webber, C. J. Newcomb, R. Bittonc, S. I. Stupp, Soft Matter 2011, 7, 9665-9672
67. X. Li, Y. Gao, Y. Kuang, B. Xu, Chem. Commun. 2010, 46, 5364-5366
68. J. Gao, W. Zheng, D. Kong, Z. Yang, Soft Matter 2011, 7, 10443-10448
69. Z. Yang, G. Liang, B. Xu, Acc. Chem. Res. 2008, 41, 315-326 and references cited therein.
70. R. Nguyen, L. Allouche, E. Buhler, N. Giuseppone, Angew. Chem. 2009, 121, 1113-1116
71. Angew. Chem. Int. Ed. 2009, 48, 1093-1096
72. C. B. Minkenberg, L. Florusse, R. Eelkema, G. J. M. Koper, J. H. van Esch, J. Am. Chem. Soc. 2009, 131, 11274-11275
73. C. B. Minkenberg, F. Li, P. van Rijn, L. Florusse, J. Boekhoven, M. C. A. Stuart, G. J. M. Koper, R. Eelkema, J. H. van Esch, Angew. Chem. 2011, 123, 3483-3486
74. Angew. Chem. Int. Ed. 2011, 50, 3421-3424
75. N. Sreenivasachary, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2005, 102, 5938-5943.
76. M. Ikeda, T. Tanida, T. Yoshii, I. Hamachi, Adv. Mater. 2011, 23, 2819-2822. For reduction-responsive supramolecular hydrogels based on the cleavage of disulfide bonds, see
77. C. J. Bowerman, B. L. Nilsson, J. Am. Chem. Soc. 2010, 132, 9526-9527
78. C. Ren, Z. Song, W. Zheng, X. Chen, L. Wang, D. Konga, Z. Yang, Chem. Commun. 2011, 47, 1619-1621.
79. Y. Chujo, S. Sada, T. Saegusa, Macromolecules 1990, 23, 2636-2641
80. X. Chen, M. A. Dam, K. Ono, A. Mal, H. Shen, S. R. Nutt, K. Sheran, F. Wudl, Science 2002, 295, 1698-1702
81. P. J. Boul, P. Reutenauer, J.-M. Lehn, Org. Lett. 2005, 7, 15-18
82. P. Reutenauer, E. Buhler, P. J. Boul, S. J. Candau, J.-M. Lehn, Chem. Eur. J. 2009, 15, 1893-1900. However, the use of the retro-DA reaction to control morphological transformation of supramolecular nanostructures has rarely been explored
83. X. Zhang, Z.-C. Li, K.-B. Li, F.-M. Du, F.-M. Li, J. Am. Chem. Soc. 2004, 126, 12200-12201
84. J. R. McElhanon, T. Zifer, S. R. Kline, d. R. Wheeler, D. A. Loy, G. M. Jamison, T. M. Long, K. Rahimian, B. A. Simmons, Langmuir 2005, 21, 3259-3266. For elegant examples that use retro-DA reactions to trigger the formation of organic semiconductor films, see
85. A. Afzali, C. D. Dimitrakopoulos, T. L. Breen, J. Am. Chem. Soc. 2002, 124, 8812-8813.
86. J. Boekhoven, A. M. Brizard, K. N. K. Kowlgi, G. J. M. Koper, R. Eelkema, J. H. van Esch, Angew. Chem. 2010, 122, 4935-4938
87. Angew. Chem. Int. Ed. 2010, 49, 4825-4828
88. Y. Tidhar, H. Weissman, S. G. Wolf, A. Gulino, B. Rybtchinski, Chem. Eur. J. 2011, 17, 6068-6075
89. P. A. Korevaar, S. J. George, A. J. Markvoort, M. M. J. Smulders, P. A. J. Hilbers, A. P. H. J. Schenning, T. F. A. De Greef, E. W. Meijer, Nature 2012, 481, 492-496.
90. Y. Okahata, T. Kunitake, J. Am. Chem. Soc. 1979, 101, 5231-5234
91. J.-H. Fuhrhop, D. Spiroski, C. Boettcher, J. Am. Chem. Soc. 1993, 115, 1600-1601
92. T. Shimizu, M. Masuda, J. Am. Chem. Soc. 1997, 119, 2812-2818. For a recent review, see
93. J.-H. Fuhrhop, T. Wang, Chem. Rev. 2004, 104, 2901-2937.
94. J. H. Jung, G. John, M. Masuda, K. Yoshida, S. Shinkai, T. Shimizu, Langmuir 2001, 17, 7229-7232.
95. E. Yashima, K. Maeda, H. Iida, Y. Furusho, K. Nagai, Chem. Rev. 2009, 109, 6102-6211
96. T. F. A. de Greef, M. M. J. Smulders, M. Wolffs, A. P. H. J. Schenning, R. P. Sijbesma, E. W. Meijer, Chem. Rev. 2009, 109, 5687-5754.