The search for molecular receptors capable of forming stable associates with fullerenes is a very active field of research in fullerene chemistry, with the purification from fullerite and the self-assembly of nanoscale electronic devices as driving forces. The construction of bivalent, tweezer-like receptors featuring two recognizing units connected through a spacer is one of the most successful design strategies employed in this field. Here, we present an overview of the most significant examples of these “molecular tweezers” for fullerenes.
Conference
International Conference on Heteroatom Chemistry (ICHAC-9), International Conference on Heteroatom Chemistry, ICHAC, Heteroatom Chemistry, 9th, Oviedo, Spain, 2009-06-30–2009-07-04
References
1 10.1038/318162a0, H. W. Kroto, J. R. Heath, S. C. O’Brien, R. F. Curl, R. E. Smalley. Nature318, 162 (1985).Search in Google Scholar
2 10.1002/anie.199211013, F. Diederich, J. Effing, U. Jonas, L. Jullien, T. Plesnivy, H. Ringsdorf, C. Thilgen, D. Weinstein. Angew. Chem., Int. Ed. Engl.31, 1599 (1992).Search in Google Scholar
3 T. Andersson, K. Nilsson, M. Sundahl, G. Westman, O. Wennerstroem. Chem. Commun. 604 (1992).10.1039/C39920000604Search in Google Scholar
4 A. Collet. Comprehensive Supramol. Chem.6, 281 (1996).Search in Google Scholar
5 10.1021/ja00101a083, J. W. Steed, P. C. Junk, J. L. Atwood, M. J. Barnes, C. L. Raston, R. S. Burkhalter. J. Am. Chem. Soc.116, 10346 (1994).Search in Google Scholar
6 10.1002/anie.200603223, E. Huerta, G. A. Metselaar, A. Fragoso, E. Santos, C. Bo, J. de Mendoza. Angew. Chem., Int. Ed.46, 202 (2007).Search in Google Scholar PubMed
7 10.1038/368229a0, J. L. Atwood, G. A. Koutsantonis, C. L. Raston. Nature368, 229 (1994).Search in Google Scholar
8 10.1246/cl.1994.699, T. Suzuki, K. Nakashima, S. Shinkai. Chem. Lett. 699 (1994).Search in Google Scholar
9 T. Haino, M. Yanase, Y. Fukazawa. Angew. Chem., Int. Ed.36, 259 (1997).Search in Google Scholar
10 10.1021/ja00483a063, The term “molecular tweezer” was coined by Whitlock to describe a molecular receptor featuring two recognizing units separated by a relatively rigid spacer. C. W. Chen, H. W. Whitlock Jr. J. Am. Chem. Soc.100, 4921 (1978).Search in Google Scholar
11 10.1021/ar030164v, M. Harmata. Acc. Chem. Res.37, 862 (2004).Search in Google Scholar PubMed
12 10.1021/ja990618c, M. M. Olmstead, D. A. Costa, K. Maitra, B. C. Noll, S. L. Phillips, P. M. Van Calcar, A. L. Balch. J. Am. Chem. Soc.121, 7090 (1999).Search in Google Scholar
13 10.1021/ar040168f, P. D. W. Boyd, C. A. Reed. Acc. Chem. Res.38, 235 (2005).Search in Google Scholar PubMed
14 10.1021/ja992416m, K. Tashiro, T. Aida, J.-Y. Zheng, K. Kinbara, K. Saigo, S. Sakamoto, K. Yamaguchi. J. Am. Chem. Soc.121, 9477 (1999).Search in Google Scholar
15 10.1039/b614883m, K. Tashiro, T. Aida. Chem. Soc. Rev.36, 189 (2007).Search in Google Scholar PubMed
16 10.1021/ja0747526, M. Yanagisawa, K. Tashiro, M. Yamasaki, T. Aida. J. Am. Chem. Soc.129, 11912 (2007).Search in Google Scholar PubMed
17 10.1021/ja063828f, Y. Shoji, K. Tashiro, T. Aida. J. Am. Chem. Soc.128, 10690 (2006).Search in Google Scholar PubMed
18 10.1021/ja002214m, D. Sun, F. S. Tham, C. A. Reed, L. Chaker, M. Burgess, P. D. W. Boyd. J. Am. Chem. Soc.122, 10704 (2000).Search in Google Scholar
19 10.1021/ja017555u, D. Sun, F. S. Tham, C. A. Reed, L. Chaker, P. D. W. Boyd. J. Am. Chem. Soc.124, 6604 (2002).Search in Google Scholar PubMed
20 10.1039/b111357g, M. Ayabe, A. Ikeda, S. Shinkai, S. Sakamoto, K. Yamaguchi. Chem. Commun. 1032 (2002).Search in Google Scholar PubMed
21 10.1021/ja056509h, Z.-Q. Wu, X.-B. Shao, C. Li, J.-L. Hou, K. Wang, X.-K. Jiang, Z.-T. Li. J. Am. Chem. Soc.127, 17460 (2005).Search in Google Scholar PubMed
22 10.1021/ja066031x, A. Hosseini, S. Taylor, G. Accorsi, N. Armaroli, C. A. Reed, P. D. W. Boyd. J. Am. Chem. Soc.128, 15903 (2006).Search in Google Scholar PubMed
23 10.1002/anie.200504313, For a leading general review in the field of synthetic molecular machines and interlocked architectures, see: E. R. Kay, D. A. Leigh, F. Zerbetto. Angew. Chem., Int. Ed.46, 72 (2007).Search in Google Scholar PubMed
24 10.1021/ol702524f, J.-S. Marois, K. Cantin, A. Desmarais, J.-F. Morin. Org. Lett.10, 33 (2008).Search in Google Scholar PubMed
25 10.1002/chem.200701686, L. H. Tong, J.-L. Wietor, W. Clegg, P. R. Raithby, S. I. Pascu, J. K. M. Sanders. Chem.—Eur. J.14, 3035 (2008).Search in Google Scholar PubMed
26 10.1039/b802589b, E. M. Pérez, N. Martín. Chem. Soc. Rev.37, 1512 (2008).Search in Google Scholar PubMed
27 10.1039/b816272g, E. M. Pérez, B. M. Illescas, M. A. Herranz, N. Martín. New J. Chem.33, 228 (2009).Search in Google Scholar
28 10.1021/cr0509657, T. Kawase, H. Kurata. Chem. Rev.106, 5250 (2006).Search in Google Scholar PubMed
29 10.1021/ja00954a049, W. E. Barth, R. G. Lawton. J. Am. Chem. Soc.88, 380 (1966).Search in Google Scholar
30 10.1021/ja070616p, A. Sygula, F. R. Fronczek, R. Sygula, P. W. Rabideau, M. M. Olmstead. J. Am. Chem. Soc.129, 3842 (2007).Search in Google Scholar PubMed
31 10.1021/ja0621389, E. M. Pérez, L. Sánchez, G. Fernández, N. Martín. J. Am. Chem. Soc.128, 7172 (2006).Search in Google Scholar PubMed
32 10.1002/anie.200604327, E. M. Pérez, M. Sierra, L. Sánchez, M. R. Torres, R. Viruela, P. M. Viruela, E. Ortí, N. Martín. Angew. Chem., Int. Ed.46, 1847 (2007).Search in Google Scholar PubMed
33 10.1021/ar700026t, N. Martín, L. Sánchez, M. A. Herranz, B. Illescas, D. M. Guldi. Acc. Chem. Res.40, 1015 (2007).Search in Google Scholar PubMed
34 10.1002/anie.200803984, S. S. Gayathri, M. Wielopolski, E. M. Pérez, G. Fernández, L. Sánchez, R. Viruela, E. Ortí, D. M. Guldi, N. Martín. Angew. Chem., Int. Ed.48, 815 (2009).Search in Google Scholar PubMed
35 10.1039/b810177a, E. M. Pérez, A. L. Capodilupo, G. Fernández, L. Sánchez, P. M. Viruela, R. Viruela, E. Ortí, M. Bietti, N. Martín. Chem. Commun. 4567 (2008).Search in Google Scholar PubMed
36 10.1002/anie.200703049, G. Fernández, E. M. Pérez, L. Sánchez, N. Martín. Angew. Chem., Int. Ed.47, 1094 (2008).Search in Google Scholar PubMed
37 10.1021/ja710505h, G. Fernández, E. M. Pérez, L. Sánchez, N. Martín. J. Am. Chem. Soc.130, 2410 (2008).Search in Google Scholar PubMed
38 10.1021/ja8018498, G. Fernández, L. Sánchez, E. M. Pérez, N. Martín. J. Am. Chem. Soc.130, 10674 (2008).Search in Google Scholar PubMed
39 After this article was sent for publication, we have succeeded in synthesizing very efficient exTTF-based macrocyclic receptors, see: H. Isla, M. Gallego, E. M. Pérez, R. Viruela, E. Ortí, N. Martín. J. Am. Chem. Soc. In press. DOI: 10.1021/ja910107m.10.1021/ja910107mSearch in Google Scholar PubMed
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