Extreme conformational constraints in π-extended tetrathiafulvalenes: Unusual topologies and redox behavior of doubly and triply bridged cyclophanes

Journal of the American Chemical Society

Volumn 128, Issue 32, 2006, Pages 10484-10490

  Christensen, Christian A ^a   Batsanov, Andrei S ^a   Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONSTRAINT THEORY; CRYSTAL STRUCTURE; OLEFINS; SYNTHESIS (CHEMICAL); TOPOLOGY;

INTRAMOLECULAR INTERACTIONS; STERIC CONSTRAINTS; X-RAY CRYSTAL STRUCTURES;

PARAFFINS;

9,10 BIS(1,3 DITHIOL 2 YLIDENE) 9,10 DIHYDROANTHRACENE; CYCLOPHANE; CYCLOPHANE DERIVATIVE; DITHIOL DERIVATIVE; REAGENT; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; CYCLIZATION; MACROCYCLIZATION; OXIDATION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 33747590165     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062358m     Document Type: Article

References (68)

1. Frère, P.; Skabara, P. J. Chem. Soc. Rev. 2005, 34, 69-98.
2. (a) Martín, N.; Ortí, E. In Handbook of Advanced Electronic Photonic Materials and Devices: Nalwa, H. S., Ed., Academic Press: San Diego, 2001; Vol. 3, Chapter 6, pp 245-265.
3. (b) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
4. (c) Yamashita, Y. In Tetrathiafulvalene Chemistry, Fundamentals and Applications of Tetrathiafulvalene; Yamada, J., Sugimoto, T., Eds.; Springer-Verlag: Berlin, 2004; Chapter 12, pp 287-310.
5. (d) Yamashita, Y.; Tanaka, S.; Imaeda, K.; Inokuchi, H.; Sano, M. J. Chem. Soc., Chem. Commun. 1991, 1132-1133.
6. (a) Hu, K.; Evans, D. H. J. Phys. Chem. 1996, 100, 3030-3036.
7. (b) Evans, D. H.; Hu, K. J. Chem. Soc., Faraday Trans. 1996, 92, 3983-3990.
8. (c) Kraiya, C.; Evans, D. H. J. Electroanal. Chem. 2004, 565, 29-35.
9. (d) Gruhn, N. E.; Macías-Ruvalcaba, N. A.; Evans, D. H. J. Phys. Chem. A 2006, 110, 5650-5655.
10. (e) Macías-Ruvalcaba, N. A.; Evans, D. H. J. Phys. Chem. B 2006, 110, 5155-5160. References 3c-e refer to 9,10-disubstituted anthracenes and emphasize that the changes in geometry which accompany the redox process are crucial in causing inverted potentials.
11. For pioneering work on the electrochemistry of two-electron redox systems, see: (a) Fritsch, J. M.; Weingarten, H.; Wilson, J. D. J. Am. Chem. Soc. 1970, 92, 4038-4046.
12. (b) Deuchert, K.; Hünig, S. Angew. Chem., Int. Ed. Engl. 1978, 17, 875-886.
13. (a) Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052-1053.
14. (b) Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 157-168.
15. (c) Bryce, M. R.; Coffin, M. A.; Hursthouse, M. B.; Karaulov, A. I.; Müllen, K.; Scheich, H. Tetrahedron Lett. 1991, 32, 6029-6032.
16. (d) Liu, S.-G.; Pérez, I.; Martín, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 9092-9102.
17. (e) Liu, S.-G.; Perez, I.; Martín, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 9092-9102.
18. For other molecular systems where significant conformational changes are triggered by electron transfer, see: (a) Boubekeur, K.; Lenoir, C.; Batail, P.; Carlier, R.; Tallec, A.; Le Paillard, M.-P.; Lorcy, D.; Robert, A. Angew. Chem., Int. Ed. Engl. 1994, 33, 1379-1381.
19. (b) Guerro, M.; Carlier, R.; Boubekeur, K.; Lorcy, D.; Hapiot, P. J. Am. Chem. Soc. 2003, 125, 3159-3167 and references therein.
20. (c) Nygaard, S.; Laursen, B. W.; Flood, A. H.; Hansen, C. N.; Jeppesen, J. O.; Stoddart, J. F. Chem. Commun. 2006, 144-146.
21. Bryce, M. R.; Moore, A. J.; Hasan, M.; Ashwell, G. J.; Fraser, A. T.; Clegg, W.; Hursthouse, M. B.; Karaulov, A. I. Angew. Chem., Int. Ed. Engl. 1990, 29, 1450-1452.
22. Martín, N.; Sánchez, L.; Seoane, C.; Ortí, E.; Viruela, P. M.; Viruela, R. J. Org. Chem. 1998, 63, 1268-1279.
23. Jones, A. E.; Christensen, C. A.; Perepichka, D. F.; Batsanov, A. S.; Beeby, A.; Low, P. J.; Bryce, M. R.; Parker, A. W. Chem. Eur. J. 2001, 7, 973-978.
24. (a) Martín, N.; Sánchez, L.; Guldi, D. M. Chem. Commun. 2000, 113-114.
25. (b) Guldi, D. M.; Sánchez, L.; Martín, N. J. Phys. Chem. B 2001, 105, 7139-7144.
26. (a) Triki, S.; Ouahab, L.; Lorcy, D.; Robert, A. Acta Crystallogr. 1993, C49, 1189-1192.
27. (b) Batsanov, A. S.; Bryce, M. R.; Lyubchik, S. B.; Perepichka, I. F. Acta Crystallogr. 2002, E58, o1106-o1110.
28. (a) Otero, M.; Herranz, M. A.; Seoane, C.; Martín, N.; Garín, J.; Orduna, J.; Alacalá, R.; Villacampa, B. Tetrahedron 2002, 58, 7463-7475.
29. (b) Insuasti, B.; Atienza, C.; Seoane, C.; Martín, N.; Garín, J.; Orduna, J.; Alacalá, R.; Villacampa, B. J. Org. Chem. 2004, 69, 6986-6995.
30. (a) Cerrada, E.; Bryce, M. R.; Moore, A. J. J. Chem. Soc., Perkin Trans. I 1993, 537-538.
31. (b) Marshallsay, G. J.; Bryce, M. R. J. Org. Chem. 1994, 59, 6847-6850.
32. (c) Gautier, N.; Mercier, N.; Riou, A.; Gorgues, A. Hudhomme, P. Tetrahedron Lett. 1998, 40, 5997-6000.
33. (a) Martín, N.; Pérez, I.; Sánchez, L.; Seoane, C. J. Org. Chem. 1997, 62, 870-877.
34. (b) Christensen, C. A.; Bryce, M. R.; Batsanov, A. S.; Becher, J. Org. Biomol. Chem. 2003, 1, 511-522.
35. (c) Díaz, M. C.; Illescas, B. M.; Seoane, C.; Martín, N. J. Org. Chem. 2004, 69, 4492-4499.
36. (d) Díaz, M. C.; Illescas, B. M.; Martín, N.; Perepichka, I. F.; Bryce, M. R.; Levillain, E.; Viruela, R.; Ortí, E. Chem. Eur. J. 2006, 12, 2709-2712.
37. (e) Díaz, M. C.; Illescas, B. M.; Martín, N.; Stoddart, J. F.; Canales, M. A.; Jiménez-Barbero, J.; Sarova, G.; Guldi, D. M. Tetrahedron 2006, 62, 1998-2002.
38. Godbert, N.; Bryce, M. R. J. Mater. Chem. 2002, 12, 27-36.
39. (a) Herranz, M. A.; Martín, N.; Ramey, J.; Guldi, D. M. Chem. Commun. 2002, 2968-2968.
40. (b) Kodis, G.; Liddell, P. A.; de la Garza, L.; Moore, A. L.; Moore, T. A.; Gust, D. J. Mater. Chem. 2002, 12, 2100-2108.
41. (c) González, S.; Martín, N.; Swartz, A.; Guldi, D. M. Org. Lett. 2003, 5, 557-560.
42. (d) Díaz, M. C.; Herranz, M. A.; Illescas, B. M.; Martin, N.; Godbert, N.; Bryce, M. R.; Luo, Ch.; Swartz, A.; Anderson, G.; Guldi, D. M. J. Org. Chem. 2003, 68, 7711-7721.
43. (e) Perepichka, D. F.; Bryce, M. R.; Perepichka, I. F.; Lyubchik, S. B.; Christensen, C. A.; Godbert, N.; Batsanov, A. S.; Levillain, E.; McInnes, E. J. L.; Zhao, J. P. J. Am. Chem. Soc. 2002, 124, 14227-14238.
44. (f) Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 5340-5341.
45. (g) Giacalone, F.; Segura, J. L.; Martín, N.; Ramey, G.; Guldi, D. M. Chem. Eur. J. 2005, 11, 4819-4834.
46. (a) Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
47. (b) Vögtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993.
48. (c) For a series of multiply bridged and sterically constrained cyclophanes, see: Song, Q.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 2005, 127, 11246-11247.
49. Finn, T.; Bryce, M. R.; Batsanov, A. S.; Howard, J. A. K. Chem. Commun. 1999, 1835-1836.
50. Godbert, N.; Batsanov, A. S.; Bryce, M. R.; Howard, J. A. K. J. Org. Chem. 2001, 66, 713-719.
51. Christensen, C. A.; Batsanov, A. S.; Bryce, M. R.; Howard, J. A. K. J. Org. Chem. 2001, 66, 3313-3320.
52. For a review of the synthesis and reactivity of cyanoethyl-protected TTF thiolates, see: Simomsen, K. B.; Becher, J. Synlett 1997, 1211-1220.
53. The development of this methodology for the synthesis of a series of new and versatile ex-TTF building blocks will be reported elsewhere.
54. Takimiya, K.; Imamura, K.; Shibata, Y.; Aso, Y.; Ogura, F.; Otsubo, T. J. Org. Chem. 1997, 62, 5567-5574.
55. Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J. Synthesis 1994, 809-812.
56. It is known that cesium hydroxide monohydrate can cleave silyl protecting groups during the deprotection of cyanoethylthio groups: Christensen, C. A.; Bryce, M. R.; Becher, J. Synthesis 2000, 1695-1704.
57. (a) Bryce, M. R.; Finn, T.; Moore, A. J.; Batsanov, A. S.; Howard, J. A. K. Eur. J. Org. Chem. 2000, 51-60.
58. (b) Godbert, N.; Bryce, M. R.; Dahaoui, S.; Batsanov, A. S.; Howard, J. A. K.; Hazendonk, P. Eur. J. Org. Chem. 2001, 749-757.
59. (c) Bryce, M. R.; Finn, T.; Batsanov, A. S.; Kataky, R.; Howard, J. A. K.; Lyubchik, S. B. Eur. J. Org. Chem. 2002, 1199-1205.
60. (a) Lau, J.; Blanchard, P.; Riou, A.; Jubault, M.; Cava, M. P.; Becher, J. J. Org. Chem. 1997, 62, 4936-4942.
61. (b) Wang, C.; Bryce, M. R.; Batsanov, A. S.; Howard, J. A. K. Chem. Eur. J. 1997, 3, 1679-1690.
62. (c) Otsubo, T.; Aso, Y.; Takimiya, K. Adv. Mater. 1996, 8, 203-211.
63. p ≈ (59/z) mV, where z is the number of electrons involved in the process.
64. pc)/2.
65. Khodorkovsky, V.; Shapiro, L.; Krief, P.; Shames, A.; Mabon, G.; Gorgues, A.; Giffard, M. Chem. Commun. 2001, 2736-2737.
66. Spanggaard, H.; Prehn, J.; Nielsen, M. B.; Levillain, E.; Allain, M.; Becher, J. J. Am. Chem. Soc. 2000, 122, 9486-9494.
67. (a) Balzani, V.; Venturi, M.; Credi, A. Molecular Devices and Machines: A Journey into the Nanaworld; Wiley-VCH: Weinheim, 2003.
68. (b) Easton, C. J.; Lincoln, S. F.; Barr, L.; Onagi, H. Chem. Eur. J. 2004, 10, 3120-3128.