Topochemical polymerization of phenylacetylene macrocycles: A new strategy for the preparation of organic nanorods

Journal of the American Chemical Society

Volumn 135, Issue 1, 2013, Pages 110-113

  Rondeau Gagné, Simon ^a   Néabo, Jules Roméo ^a   Desroches, Maude ^a   Larouche, Jérémie ^a   Brisson, Josée ^a   Morin, Jean Francìois ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE GROUPS; BUTADIYNE; ETHYL ACETATES; MACROCYCLES; ORGANOGELS; PHENYLACETYLENES; RAMAN SIGNAL; SELF-ASSEMBLED; TOPOCHEMICAL POLYMERIZATION;

AMIDES; AROMATIC HYDROCARBONS; NANORODS; POLYMERIZATION; RAMAN SPECTROSCOPY;

ACETYLENE;

ACETIC ACID ETHYL ESTER; AMIDE; MACROCYCLIC COMPOUND; NANOROD; PHENYLACETYLENE;

ARTICLE; POLYMERIZATION; RAMAN SPECTROMETRY; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

ACETYLENE; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; NANOTUBES; POLYMERIZATION;

EID: 84872099101     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3116422     Document Type: Article

References (29)

1. Prince, R. B.; Okada, T.; Moore, J. S. Angew. Chem., Int. Ed. 1999, 38, 233
2. Prince, R. B.; Barnes, S. A.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 2758
3. Organo, V. G.; Rudkevich, D. M. Chem. Commun. 2007, 3891
4. Tan, C.; Pinto, M. R.; Kose, M. E.; Ghiviriga, I.; Schanze, K. S. Adv. Mater. 2004, 16, 1208
5. Tanatani, A.; Mio, M. J.; Moore, J. S. J. Am. Chem. Soc. 2001, 123, 1792
6. Block, M. A. B.; Kaiser, C.; Khan, A.; Hecht, S. Top. Curr. Chem. 2005, 245, 89
7. Dawn, S.; Dewal, M. B.; Sobransingh, D.; Paderes, M. C.; Wibowo, A. C.; Smith, M. D.; Krause, J. A.; Pellechia, P. J.; Shimizu, L. S. J. Am. Chem. Soc. 2011, 133, 7025
8. Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516
9. Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E.; Khazanovich, N. Nature 1993, 366, 324
10. Ikeda, A.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 2375
11. Wegner, G. Z. Naturforsch., B: J. Chem. Sci. 1969, 24, 824
12. Wegner, G. Makromol. Chem. 1972, 154, 35
13. Hisaki, I.; Sakamoto, Y.; Shigemitsu, H.; Tohnai, N.; Miyata, M. Cryst. Growth. Des. 2009, 9, 414
14. Zhou, Q.; Carroll, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294
15. Suzuki, M.; Comito, A.; Khan, S. I.; Rubin, Y. Org. Lett. 2010, 12, 2346
16. Nishinaga, T.; Nodera, N.; Miyata, Y.; Komatsu, K. J. Org. Chem. 2002, 67, 6091
17. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052
18. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956
19. Nomoto, A.; Sonoda, M.; Yamaguchi, Y.; Ichikawa, T.; Hirose, K.; Tobe, Y. J. Org. Chem. 2006, 71, 401
20. Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215
21. Cantin, K.; Rondeau-Gagné, S.; Néabo, J. R.; Daigle, M.; Morin, J.-F. Org. Biomol. Chem. 2011, 9, 4440
22. Néabo, J. R.; Tohoundjona, K. I. S.; Morin, J.-F. Org. Lett. 2011, 13, 1358
23. During the course of this study, Tamaoki and co-workers reported the formation of nanotubes from flexible, non-phenylacetylene macrocycles using UV irradiation. See: Nagasawa, J.; Yoshida, M.; Tamaoki, N. Eur. J. Org. Chem. 2011, 2247
24. Xu, Y.; Smith, M. D.; Geer, M. F.; Pellechia, P. J.; Brown, J. C.; Wibowo, A. C.; Shimizu, L. S. J. Am. Chem. Soc. 2010, 132, 5334
25. Hsu, T.-J.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 2012, 134, 142
26. Xie, H.; Zhang, S.; Li, H.; Zhang, X.; Zhao, S.; Xu, Z.; Song, X.; Yu, X.; Wang, W. Chem.-Eur. J. 2012, 18, 2230
27. Zhang, P.; Wang, H.; Liu, H.; Li, M. Langmuir 2010, 26, 10183
28. Balakrishnan, K.; Datar, A.; Zhang, W.; Yang, X.; Naddo, T.; Huang, J.; Zuo, J.; Yen, M.; Moore, J. S.; Zang, L. J. Am. Chem. Soc. 2006, 128, 6576
29. Shimura, H.; Yoshio, M.; Kato, T. Org. Biomol. Chem. 2009, 7, 3205