An investigation of the role of the disparate redox states of the tetrathiafulvalene unit in modulating hydrogen bonding interactions in solution

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 303-306

  Boyd, Alan S F ^a   Cooke, Graeme ^a   Duclairoir, Florence M A ^a   Rotello, Vincent M ^b  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Electrochemistry; Recognition; Tetrathiafulvalene

Indexed keywords

TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTRODE; HYDROGEN BOND; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PRECIPITATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECIES;

EID: 0037421076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02574-1     Document Type: Article

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15. For review articles which focus upon the applications of TTF within supramolecular chemistry see: (a) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372; (b) Nielsen, M. B.; Lomholt, C.; Becher, J. Chem. Soc. Rev. 2000, 29, 153; (c) Jørgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 23, 41.
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18. 3. However, similar shifts in the half-wave potentials of the CV of 3 were observed regardless of which amide guest was added.
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20. 2, TMS): δ 24.04, 106.90, 111.70, 113.83, 119.97, 120.25, 120.61, 127.59, 134.94, 139.20, 151.76, 157.84, 158.55; MS (EI): m/z=338 (M+).
21. -1. T=25°C.
22. For examples of host-guest complexation that prevents precipitation of the redox-active component at the working electrode see: (a) Gallow, T. H.; Ilhan, F.; Cooke, G.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 3595; (b) González, B.; Casado, C. M.; Alonso, B.; Cuadrado, I.; Morán, M.; Wang, Y.; Kaifer A. Chem. Commun. 1998, 2569; (c) Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
23. For examples of host-guest complexation that prevents precipitation of the redox-active component at the working electrode see: (a) Gallow, T. H.; Ilhan, F.; Cooke, G.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 3595; (b) González, B.; Casado, C. M.; Alonso, B.; Cuadrado, I.; Morán, M.; Wang, Y.; Kaifer A. Chem. Commun. 1998, 2569; (c) Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
24. For examples of host-guest complexation that prevents precipitation of the redox-active component at the working electrode see: (a) Gallow, T. H.; Ilhan, F.; Cooke, G.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 3595; (b) González, B.; Casado, C. M.; Alonso, B.; Cuadrado, I.; Morán, M.; Wang, Y.; Kaifer A. Chem. Commun. 1998, 2569; (c) Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
25. All calculations reported here were performed using the Gaussian 98W (version 5.4), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1998.