Conductive one-handed nanocoils by coassembly of hexabenzocoronenes: Control of morphology and helical chirality

Angewandte Chemie - International Edition

Volumn 47, Issue 9, 2008, Pages 1672-1675

  Yamamoto, Takuya ^b   Fukushima, Takanori ^a,b   Kosaka, Atsuko ^b   Jin, Wusong ^b   Yamamoto, Yohei ^b   Ishii, Noriyuki ^c   Aida, Takuzo ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Chirality; Conducting materials; Polymerization; Self assembly; Supramolecular chemistry

Indexed keywords

STEREOCHEMISTRY;

CHIRALITY; CONDUCTING MATERIALS; POLYMERIZATION; SUPRAMOLECULAR CHEMISTRY;

SELF ASSEMBLY;

NANOMATERIAL; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; ELECTRIC CONDUCTIVITY; ELECTROMAGNETIC FIELD; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; ULTRASTRUCTURE;

CIRCULAR DICHROISM; ELECTRIC CONDUCTIVITY; ELECTROMAGNETICS; MICROSCOPY, ELECTRON, SCANNING; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; NANOSTRUCTURES; POLYCYCLIC COMPOUNDS;

EID: 41049092871     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704747     Document Type: Article

References (35)

1. J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995.
2. For recent reviews, see: a) F. Würthner, Chem. Commun. 2004, 1564-1579;
3. b) T. Shimizu, M. Masuda, H. Minamikawa, Chem. Rev. 2005, 105, 1401-1443;
4. c) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546;
5. d) J. Wu, W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718-747.
6. See, for example: a) J. J. L. M. Cornelissen, M. Fischer, N. A. J. M. Sommerdijk, R. J. M. Nolte, Science 1998, 280, 1427-1430;
7. b) J. H. Jung, G. John, K. Yoshida, T. Shimizu, J. Am. Chem. Soc. 2002, 124, 10674-10675;
8. c) B. W. Messmore, P. A. Sukerkar, S. I. Stupp, J. Am. Chem. Soc. 2005, 127, 7992-7993;
9. d) J. Bae, J.-H. Choi, Y.-S. Yoo, N.-K. Oh, B.-S. Kim, M. Lee, J. Am. Chem. Soc. 2005, 127, 9668-9669.
10. a) A. J. Lovinger, C. Nuckolls, T. J. Katz, J. Am. Chem. Soc. 1998, 120, 264-268;
11. b) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788;
12. c) A. Ajayaghosh, R. Varghese, S. J. George, C. Vijayakumar, Angew. Chem. 2006, 118, 1159-1162;
13. Angew. Chem. Int. Ed. 2006, 45, 1141-1144;
14. d) A. Ajayaghosh, R. Varghese, S. Mahesh, V. K. Praveen, Angew. Chem. 2006, 118, 7893-7896;
15. Angew. Chem. Int. Ed. 2006, 45, 7729-7732;
16. e) W.-Y. Yang, E. Lee, M. Lee, J. Am. Chem. Soc. 2006, 128, 3484-3485.
17. J. P. Hill, W. Jin, A. Kosaka, T. Fukushima, H. Ichihara, T. Shimomura, K. Ito, T. Hashizume, N. Ishii, T. Aida, Science 2004, 304, 1481-1483.
18. T. Yamamoto, T. Fukushima, Y. Yamamoto, A. Kosaka, W. Jin, N. Ishii, T. Aida, J. Am. Chem. Soc. 2006, 128, 14337-14340.
19. W. Jin, T. Fukushima, M. Niki, A. Kosaka, N. Ishii, T. Aida, Proc. Natl. Acad. Sci. USA 2005, 102, 10801-10806.
20. See the Supporting Information.
21. For a review, see: M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3328-3345;
22. Angew. Chem. Int. Ed. 1999, 38, 3138-3154.
23. For examples of the sergeants-and-soldiers effect in supramolecular systems, see: a) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
24. b) L. J. Prins, E. E. Neuteboom, V. Paraschiv, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt, J. Org. Chem. 2002, 67, 4808-4820;
25. c) M. De Napoli, S. Nardis, R. Paolesse, M. G. H. Vicente, R. Lauceri, R. Purrello, J. Am. Chem. Soc. 2004, 126, 5934-5935;
26. d) D. Ogata, T. Shikata, K. Hanabusa, J. Phys. Chem. B 2004, 108, 15503-15510;
27. e) J. van Gestel, Macromolecules 2004, 37, 3894-3898;
28. f) J. J. D. de Jong, T. D. Tiemersma-Wegman, J. H. van Esch, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 13804-13805;
29. g) A. J. Wilson, J. van Gestel, R. P. Sijbesma, E. W. Meijer, Chem. Commun. 2006, 4404-4406.
30. a) V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H.-W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 419, 384-387;
31. b) F. J. M. Hoeben, L. M. Herz, C. Daniel, P. Jonkheijm, A. P. H. J. Schenning, C. Silva, S. C. J. Meskers, D. Beljonne, R. T. Phillips, R. H. Friend, E. W. Meijer, Angew. Chem. 2004, 116, 2010-2013;
32. Angew. Chem. Int. Ed. 2004, 43, 1976-1979;
33. c) H. A. Behanna, K. Rajangam, S. I. Stupp, J. Am. Chem. Soc. 2007, 129, 321-327;
34. d) X. Zhang, Z. Chen, F. Würthner, J. Am. Chem. Soc. 2007, 129, 4886-4887;
35. e) Y. Yamamoto, T. Fukushima, A. Saeki, S. Seki, S. Tagawa, N. Ishii, T. Aida, J. Am. Chem. Soc. 2007, 129, 9276-9277.