Mono- and bis(tetrathiafulvalene)-1,3,5-triazines as covalently linked donor-acceptor systems: Structural, spectroscopic, and theoretical investigations

Chemistry - A European Journal

Volumn 15, Issue 2, 2009, Pages 380-387

  Riobé, François ^a   Grosshans, Philippe ^b   Sidorenkova, Helena ^b   Geoffroy, Michel ^b   Avarvari, Narcis ^a  

^a UNIVERSITÉ D'ANGERS   (France)

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Charge transfer; Donor acceptor systems; EPR spectroscopy; Nitrogen heterocycles; Structure elucidation; Tetrathiafulvalenes

Indexed keywords

CHARGE TRANSFER; CYCLIC VOLTAMMETRY; ELECTRON RESONANCE; ELECTRON SPIN RESONANCE SPECTROSCOPY; ION EXCHANGE; MASS TRANSFER; OXIDATION; PARAMAGNETIC RESONANCE; QUANTUM THEORY; SODIUM; SPIN DYNAMICS; SULFUR COMPOUNDS;

DONOR-ACCEPTOR SYSTEMS; EPR SPECTROSCOPY; NITROGEN HETEROCYCLES; STRUCTURE ELUCIDATION; TETRATHIAFULVALENES;

ABSORPTION SPECTROSCOPY;

EID: 58449095839     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801851     Document Type: Article

References (48)

1. a) J. L. Segura, N. Martin, Angew. Chem. 2001, 113, 1416;
2. Angew. Chem. Int. Ed. 2001, 40, 1372;
3. b) J.-L. Yamada, TTF Chemistry: Fundamentals and Applications of Tetrathiafulvalene, Springer, Heidelberg, 2004.
4. T. Ishiguro, K. Yamaji, G. Saito, Organic Superconductors, Springer, Heidelberg, 1998.
5. a) M. R. Bryce, Adv. Mater. 1999, 11, 11;
6. b) M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891.
7. A. Aviram, M. A. Ratner, Chem. Phys. Lett. 1974, 29, 277.
8. a) C. Jia, S.-X. Liu, C. Tanner, C. Leiggener, A. Neels, L. Sanguinet, E. Levillain, S. Leutwyler, A. Hauser, S. Decurtins, Chem. Eur. J. 2007, 13, 3804;
9. b) C. Goze, C. Leiggener, S.-X. Liu, L. Sanguinet, E. Levillain, A. Hauser, S. Decurtins, ChemPhysChem 2007, 8, 1504.
10. N. Gautier, F. Dumur, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, P. Hudhomme, Angew. Chem. 2003, 115, 2871;
11. Angew. Chem. Int. Ed. 2003, 42, 2765.
12. Naraso, J. Nishida, M. Tomura, Y. Yamashita, Synth. Met. 2005, 153, 389.
13. C. Loosli, C. Jia, S.-X. Liu, M. Haas, M. Dias, E. Levillain, A. Neels, G. Labat, A. Hauser, S. Decurtins, J. Org. Chem. 2005, 70, 4988.
14. D. F. Perepichka, M. R. Bryce, C. Pearson, M. C. Petty, E. J. L. McInnes, J. P. Zhao, Angew. Chem. 2003, 115, 4784;
15. Angew. Chem. Int. Ed. 2003, 42, 4636.
16. a) D. F. Perepichka, M. R. Bryce, A. S. Batsanov, J. A. K. Howard, A. O. Cuello, M. Gray, V. M. Rotello, J. Org. Chem. 2001, 66, 4517;
17. b) J. Wu, S.-X. Liu, A. Neels, F. Le Derf, M. Sallé, S. Decurtins, Tetrahedron 2007, 63, 11282.
18. D. M. Guldi, F. Giacalone, G. de la Torre, J. L. Segura, N. Martin, Chem. Eur. J. 2005, 11, 7199.
19. M. Á. Herranz, N. Martin, S. Campidelli, M. Prato, G. Brehm, D. M. Guldi, Angew. Chem. 2006, 118, 4590;
20. Angew. Chem. Int. Ed. 2006, 45, 4478.
21. G. Ho, J. R. Heath, M. Kondratenko, D. F. Perepichka, K. Arseneault, M. Pézolet, M. R. Bryce, Chem. Eur. J. 2005, 11, 2914.
22. T. Murata, Y. Morita, Y. Yakiyama, Y. Nishimura, T. Ise, D. Shiomi, K. Sato, T. Takui, K. Nakasuji, Chem. Commun. 2007, 4009.
23. L. M. Goldenberg, J. Y. Becker, O. P.-T. Levi, V. Y. Khodorkovsky, L. M. Shapiro, M. R. Bryce, J. P. Cresswell, M. C. Petty, J. Mater. Chem. 1997, 7, 901.
24. R. Andreu, I. Malfant, P. G. Lacroix, P. Cassoux, Eur. J. Org. Chem. 2000, 737.
25. Y.-P. Zhao, L.-Z. Wu, G. Si, Y. Liu, H. Xue, L.-P. Zhang, C.-H. Tung, J. Org. Chem. 2007, 72, 3632.
26. C. Goze, S.-X. Liu, C. Leiggener, L. Sanguinet, E. Levillain, A. Hauser, S. Decurtins, Tetrahedron 2008, 64, 1345.
27. a) O. P.-T. Levi, J. Y. Becker, A. Ellern, V. Khodorkovsky, Tetrahedron Lett. 2001, 42, 1571;
28. b) Q.-Y. Zhu, Y. Liu, W. Lu, Y. Zhang, G.-Q. Bian, G.-Y. Niu, J. Dai, Inorg. Chem. 2007, 46, 10065.
29. S. Nishida, Y. Morita, K. Fukui, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Angew. Chem. 2005, 117, 7443;
30. Angew. Chem. Int. Ed. 2005, 44, 7277.
31. S. Bouguessa, A. K. Gouasmia, S. Golhen, L. Ouahab, J. M. Fabre, Tetrahedron Lett. 2003, 44, 9275.
32. a) J. Pang, Y. Tao, S. Freiberg, X.-P. Yang, M. D'Iorio, S. Wang, J. Mater. Chem. 2002, 12, 206;
33. b) T. Murase, M. Fujita, J. Org. Chem. 2005, 70, 9269.
34. G. Cooke, A. K. Powell, S. L. Heath, Synthesis 1995, 1411.
35. Experimental details and characterization of compounds, X-ray data, UV-Vis spectra, cyclic voltammetry details, theoretical calculations details are provided in the Supporting Information. CCDC 670739 (1)and 670740 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
36. a) M. Mas-Torrent, M. Durkut, P. Hadley, X. Ribas, C. Rovira, J. Am. Chem. Soc. 2004, 126, 984;
37. b) M. Mas-Torrent, C. Rovira, J. Mater. Chem. 2006, 16, 433.
38. M. Behl, R. Zentel, Macromol Chem. Phys. 2004, 205, 1633.
39. a) M. Iyoda, M. Fukuda, M. Yoshida, S. Sasaki, Chem. Lett. 1994, 2369;
40. b) M. Iyoda, M. Fukuda, S. Sasaki, M. Yoshida, Synth. Met. 1995, 70, 1171.
41. H. Mizouchi, A. Ikawa, H. Fukutome, J. Am. Chem. Soc. 1995, 117, 3260.
42. J. Yamauchi, T. Aoyama, K. Kanemoto, S. Sasaki, M. Iyoda, J. Phys. Org. Chem. 2000, 13, 197.
43. R. M. Dupeyre, H. Lemaire, A. Rassat, J. Am. Chem. Soc. 1965, 87, 3771.
44. R. Ziessel, G. Ulrich, R. C. Lawson, L. Echegoyen, J. Mater. Chem. 1999, 9, 1435.
45. G. M. Sheldrick, Programs for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany), 1996.
46. Gaussian 03, Revision B.03, M. J. Frisch, O. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
47. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
48. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.