Self-assembly of a dendron-attached tetrathiafulvalene: Gel formation and modulation in the presence of chloranil and metal ions

Small

Volumn 8, Issue 4, 2012, Pages 578-584

  Yang, Xingyuan ^a   Zhang, Guanxin ^a   Li, Liqiang ^b   Zhang, Deqing ^a   Chi, Lifeng ^b   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

chloranil; molecular responsive gels; redox reactions; self assembly; tetrathiafulvalene

Indexed keywords

ATOMIC FORCE MICROSCOPES; CHLORANIL; DENDRONS; GEL FORMATION; GEL PHASE; GELATORS; MOLECULAR GELS; OXIDATION STATE; SCANNING ELECTRON MICROSCOPE; SELF-ASSEMBLE; SPECTROSCOPIC INVESTIGATIONS; TETRATHIAFULVALENES; TWO-COMPONENT;

ATOMIC FORCE MICROSCOPY; DENDRIMERS; ELECTRON SPIN RESONANCE SPECTROSCOPY; LEAD; MAGNESIUM; METAL IONS; NANOFIBERS; REDOX REACTIONS; ROPE; SCANDIUM; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SOLVENTS;

GELS;

EID: 84863136203     PISSN: 16136810     EISSN: 16136829     Source Type: Journal    
DOI: 10.1002/smll.201101917     Document Type: Article

References (66)

1. a) A. C. Grimsdale, K. Müllen, Angew. Chem. 2005, 117, 5732-5772
2. Angew. Chem., Int. Ed. 2005, 44, 5592-5629
3. b) C. C. Lee, C. Grenier, E. W. Meijer, A. P. H. J. Schenning, Chem. Soc. Rev. 2009, 38, 671-683
4. c) K. Sakakibara, Jonathan. P. Hill, K. Ariga, Small 2011, 7, 1288-1308
5. d) K. J. M. Bishop, C. E. Wilmer, S. Soh, B. A. Grzybowski, Small 2009, 5, 1600-1630.
6. a) L. Zang, Y. Che, J. F. Moore, Acc. Chem. Res. 2008, 41, 1596-1608
7. b) L. C. Palmer, S. I. Stupp, Acc. Chem. Res. 2008, 41, 1674-1684
8. c) H. B. Liu, J. L. Xu, Y. J. Li, Y. L. Li, Acc. Chem. Res. 2010, 43, 1496-1508.
9. a) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3159
10. b) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836
11. c) M. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489-497.
12. a) A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644-656
13. b) S. Srinivasan, P. A. Babu, S. Mahesh, A. Ajayaghosh, J. Am. Chem. Soc. 2009, 131, 15122-15123
14. c) S. Srinivasan, S. S. Babu, V. K. Praveen, A. Ajayaghosh, Angew. Chem. Int. Ed. 2008, 47, 5746-5749
15. d) A. Dawn, T. Shiraki, S. Haraguchi, S. Tamaru, S. Shinkai, Chem. Asian J. 2011, 6, 266-3282.
16. a) A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, Chem. Soc. Rev. 2008, 37, 109-122
17. b) M. Suzuki, K. Hanabusa, Chem. Soc. Rev. 2009, 38, 967-975
18. c) M. O. M. Piepenbrock, G. O. Lloyd, N. Clarke, J. W. Steed, Chem. Rev. 2010, 110, 1960-2004
19. d) J. W. Steed, Chem. Soc. Rev. 2010, 39, 3686-3699
20. e) M. Suzuki, K. Hanabusa, Chem. Soc. Rev. 2010, 39, 455-463
21. f) M. Suzuki, K. Hanabusa, Chem. Soc. Rev. 2010, 39, 5067-5067
22. g) Y. Zhang, Y. Kuang, Y. Guo, B. Xu, Langmuir 2011, 27, 529-537.
23. a) Kiyonaka, K. Sada, I. Yoshimura, S. Shinkai, N. Kato, I. Hamachi, Nat. Mater. 2004, 3, 58-64
24. b) I. Yoshimura, Y. Miyahara, N. Kasagi, H. Yamane, A. Ojida, I. Hamachi, J. Am. Chem. Soc. 2004, 126, 12204-12205.
25. a) J. J. D. de Jong, L. N. Lucas, R. M. Kellogg, J. H. van Esch, B. L. Feringa, Science 2004, 304, 278-281
26. b) S. Yagai, T. Nakajima, K. Kishikawa, S. Kohmoto, T. Karatsu, A. Kitamura, J. Am. Chem. Soc. 2005, 127, 11134-11139
27. c) N. S. S. Kumar, S. Varghese, G. Narayan, S. Das, Angew. Chem. 2006, 118, 6465-6469
28. Angew. Chem. Int. Ed. 2006, 45, 6317-6321
29. d) K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676
30. e) S. Yagai, T. Iwashima, K. Kishikawa, S. Nakahara, T. Karatsu, A. Kitamura, Chem. Eur. J. 2006, 12, 3984-3994
31. f) M. Ayabe, T. Kishida, N. Fujita, K. Sada, S. Shinkai, Org. Biomol. Chem. 2003, 1, 2744-2747.
32. a) S. Wang, W. Shen, Y. L. Feng, H. Tian, Chem. Commun. 2006, 1497-1499
33. b) Q. Chen, Y. Feng, D. Q. Zhang, G. X. Zhang, Q. H. Fan, S. N. Sun, D. B. Zhu, Adv. Funct. Mater. 2010, 20, 36-42
34. c) Q. Chen, D. Zhang, G. Zhang, X. Yang, Y. Feng, Q. Fan, D. Zhu, Adv. Funct. Mater. 2010, 20, 3244-3251.
35. a) S. Kawano, N. Fujita, S. Shinkai, J. Am. Chem. Soc. 2004, 126, 8592-8593
36. b) J. Liu, P. L. He, J. L. Yan, X. H. Fang, J. X. Peng, K. Q. Liu, Y. Fang, Adv. Mater. 2008, 20, 2508-2511.
37. a) T. Akutagawa, K. Kakiuchi, T. Hasegawa, S. Noro, T. Nakamura, H. Hasegawa, S. Mashiko, J. Becher, Angew. Chem. 2005, 117, 7449-7453
38. Angew. Chem. Int. Ed. 2005, 44, 7283-7287
39. b) T. Kitahara, M. Shirakawa, S. Kawano, U. Beginn, N. Fujita, S. Shinkai, J. Am. Chem. Soc. 2005, 127, 14980-14981
40. c) T. Kitamura, S. Nakaso, N. Mizoshita, Y. Tochigi, T. Shimomura, M. Moriyama, K. Ito, T. Kato, J. Am. Chem. Soc. 2005, 127, 14769-14775.
41. a) J. Puigmarti-Luis, V. Laukhin, A. P. del Pino, J. Vidal-Gancedo, C. Rovira, E. Laukhina, D. B. Amabilino, Angew. Chem. 2007, 119, 242-245
42. Angew. Chem. Int. Ed. 2007, 46, 238-241
43. b) Y. L. Zhao, I. Aprahamian, A. Trabolsi, N. Erina, J. F. Stoddart, J. Am. Chem. Soc. 2008, 130, 6348-6350
44. c) I. Danila, F. Riobe, J. Puigmarti-Luis, A. P. del Pino, J. D. Wallis, D. B. Amabilino, N. Avarvari, J. Mater. Chem. 2009, 19, 4495-4504.
45. a) C. Wang, D. Q. Zhang, D. B. Zhu, J. Am. Chem. Soc. 2005, 127, 16372-16373
46. b) C. Wang, F. Sun, D. Q. Zhang, G. X. Zhang, D. B. Zhu, Chin. J. Chem. 2010, 28, 622-626
47. c) C. Wang, Q. Chen, F. Sun, D. Q. Zhang, G. X. Zhang, Y. Y. Huang, R. Zhao, D. B. Zhu, J. Am. Chem. Soc. 2010, 132, 3092-3096
48. d) X. Y. Yang, G. X. Zhang, D. Q. Zhang, D. B. Zhu, Langmuir 2010, 26, 11720-11725.
49. D. Canevet, M. Sallé, G. Zhang, D. Zhang, D. Zhu, Chem. Commun. 2009, 2245-2269.
50. a) Q. Chen, D. Q. Zhang, G. X. Zhang, D. B. Zhu, Langmuir 2009, 25, 11436-11441
51. b) Q. Chen, Y. X. Lv, D. Q. Zhang, G. X. Zhang, C. Y. Liu, D. B. Zhu, Langmuir 2010, 26, 3165-3168.
52. Y. Feng, Z. Liu, J. Liu, Y. M. He, Q. Y. Zeng, Q. H. Fan, J. Am. Chem. Soc. 2009, 131, 7950-7951.
53. a) H. Wu, D. Zhang, L. Su, K. Ohkubo, C. Zhang, S. Yin, L. Mao, Z. Shuai, S. Fukuzumi, D. Zhu, J. Am. Chem. Soc. 2007, 129, 6839-6846
54. b) H. Wu, D. Zhang, G. Zhang, D. Zhu, J. Org. Chem. 2008, 73, 4271-4274
55. c) H. Wu, D. Zhang, D. Zhu, Tetrahedron Lett. 2007, 48, 8951-8955
56. d) Y. Zeng, G. Zhang, D. Zhang, D. Zhu, J. Org. Chem. 2009, 74, 4375-4378
57. e) L. Jia, G. Zhang, D. Zhang, D. Zhu, Tetrahedron Lett. 2010, 51, 4515-34518
58. f) L. Jia, G. Zhang, D. Zhang, J. Xiang, W. Xu, D. Zhu, Chem. Commun. 2011, 47, 322-324
59. g) F. Sun, F. Hu, G. Zhang, Q. Zheng, D. Zhang, J. Org. Chem. 2011, 76, 6883-6888.
60. a) C. Y. Jia, D. Q. Zhang, W. Xu, X. F. Shao, D. B. Zhu, Synth. Met. 2003, 132, 1345-1346
61. b) X. Guo, Z. Gan, H. Luo, Y. Araki, D. Zhang, D. Zhu, O. Ito, J. Phys. Chem. A 2003, 107, 9747-9753.
62. H. Spanggaard, J. Prehn, M. B. Nielsen, E. Levillain, M. Allain, J. Becher, J. Am. Chem. Soc. 2000, 122, 9486-9494.
63. 2-) species, the ESR signal due to the radical anion cannot be detected. See references: a), S. Fukuzumi, K. Ohkubo, Coord. Chem. Rev. 2010, 254, 372-385
64. b) S. Fukuzumi, K. Okamoto, H. Imahori, Angew. Chem. 2002, 114, 642-644
65. Angew. Chem. Int. Ed. 2002, 41, 620-622
66. c) S. Fukuzumi, N. Nishizawa, T. Tanaka, J. Chem. Soc., Perkin Trans. 2 1985, 371-378.