Fixed or invertible calixarene-based directional shuttles

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2650-2653

  Pierro, Teresa ^a   Gaeta, Carmine ^a   Talotta, Carmen ^a   Casapullo, Agostino ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; ROTAXANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

CALIXARENES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ROTAXANES;

EID: 79956083966     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200753c     Document Type: Article

References (25)

1. Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology; Sauvage, J.-P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, 1999.
2. Saha, S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 77
3. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72
4. Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines, 2 nd ed.; Wiley-VCH: Weinheim, 2008.
5. For recent examples, see: Davidson, G. J. E.; Sharma, S.; Loeb, S. J. Angew. Chem., Int. Ed. 2010, 49, 4938
6. See also, ref 1, pp 146-152.
7. For recent examples, see: Panman, M. R.; Bodis, P.; Shaw, D. J.; Bakker, B. H.; Newton, A. C.; Kay, E. R.; Brouwer, A. M.; Buma, W. J.; Leigh, D. A.; Woutersen, S. Science 2010, 328, 125
8. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Chem. Rev. 2009, 109, 5974
9. Qu, D.-H.; Wang, Q.-C.; Tian, H. Angew. Chem., Int. Ed. 2005, 44, 5296
10. To the best of our knowledge, only examples of one-station calix[6]arene-based rotaxane systems in which a calix wheel encircles a viologen axle have been reported so far. In these instances, no shuttling or inversion motion of the calix wheel has been evidenced: Arduini, A.; Bussolati, R.; Credi, A.; Pochini, A.; Silvi, S.; Venturi, M. Tetrahedron 2008, 64, 8279
11. Arduini, A.; Ciesa, F.; Fragassi, M.; Pochini, A.; Secchi, A. Angew. Chem., Int. Ed. 2005, 44, 278
12. Arduini, A.; Ferdani, R.; Pochini, A.; Secchi, A.; Ugozzoli, F. Angew. Chem., Int. Ed. 2000, 39, 3453 For an example of self-threaded calixarene rotaxane, see: Moerkerke, S.; Ménand, M.; Jabin, I. Chem.-Eur. J. 2010, 16, 11712
13. D'Souza, D. M.; Leigh, D. A.; Mottier, L.; Mullen, K. M.; Paolucci, F.; Teat, S. J.; Zhang, S. J. Am. Chem. Soc. 2010, 132, 9465
14. Collin, J.-P.; Durola, F.; Mobian, P.; Sauvage, J.-P. Eur. J. Inorg. Chem. 2007, 2420
15. A "ring flipping" has been observed for some nondirectional crown ether-based rotaxanes, which cannot be considered as a "truly" inversion of the flat wheel: Iijima, T.; Vignon, S. A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J. K. M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J. F. Chem.-Eur. J. 2004, 10, 6375
16. Gutsche, C. D. Calixarenes, An Introduction; Royal Society of Chemistry: Cambridge, UK, 2008.
17. Strauss, S. H. Chem. Rev. 1993, 93, 927
18. Nishida, H.; Takada, N.; Yoshimura, M.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1984, 57, 2600 For a recent review on counterion effects in supramolecular chemistry, see: Gasa, T. B.; Valente, C.; Stoddart, J. F. Chem. Soc. Rev. 2011, 40, 57
19. Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092
20. Talotta, C.; Gaeta, C.; Pierro, T.; Neri, P. Org. Lett. 2011, 13, 2098
21. See the Supporting Information for further details.
22. MacroModel-9.0/Maestro-4.1 program: Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440
23. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935
24. 2Ar signals of [2]rotaxane 4b occurs at temperatures surely higher than 403 K in TCDE. Therefore, an energy barrier surely higher than 18.4 kcal/mol can be estimated for the cone-to-cone inversion of the calix wheel in [2]rotaxane 4b.
25. For comparison, the difficulty associated with the passage of a p -xylylene spacer through the cavity of a dibenzo[24]crown-8 macroring has been highlighted: Cao, J.; Fyfe, M. C. T.; Stoddart, J. F. J. Org. Chem. 2000, 65, 1937