Trimethyltetrathiafulvalene bearing an N-methylpyridinium substituent: Synthesis, crystal structures, and charge transfer properties

European Journal of Organic Chemistry

Volumn , Issue 1, 2001, Pages 73-78

  Moore, Adrian J ^a   Batsanov, Andrei S ^a   Bryce, Martin R ^a   Howard, Judith A K ^a   Khodorkovsky, Vladimir ^b   Shapiro, Lev ^b   Shames, Alex ^b  

^a DURHAM UNIVERSITY   (United Kingdom)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

Charge transfer; Crystal structures; Electron donors; Tetracyano p quinodimethane; Tetrathiafulvalenes

Indexed keywords

4,4',5 TRIMETHYL 5' (4 PYRIDYL)TETRATHIAFULVALENE; PYRIDINE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE; TRIMETHYLTETRATHIAFULVALENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTRIC CONDUCTIVITY; ELECTRICITY; OXIDATION REDUCTION POTENTIAL; QUANTUM MECHANICS; REACTION ANALYSIS; SEMICONDUCTOR; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0035133187     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200101)2001:1<73::AID-EJOC73>3.0.CO;2-0     Document Type: Article

References (26)

1. Recent reviews: [1a] P. Batail, K. Boubekeur, M. Fourmigué, J.-C. P. Gabriel, Chem. Mater. 1998, 10, 3005-3015.
2. [1b] Y. Yamashita, M. Tomura, J. Mater. Chem. 1998, 8, 1933-1944.
3. [1c] J. Yamada, H. Nishikawa, K. Kikuchi, J. Mater. Chem. 1999, 9, 617-628.
4. Review: M. R. Bryce, Adv. Mater. 1999, 11, 11-23.
5. [3a] S. Scheib, M. P. Cava, J. W. Baldwin, R. M. Metzger, J. Org. Chem. 1998, 63, 1198-1204.
6. [3b] E. Tsiperman, T. Regev, J. Y. Becker, J. Bernstein, A. Ellern, V. Khodorkovsky, A. Shames, L. Shapiro, Chem. Commun. 1999, 1125-1126.
7. P. de Miguel, M. R. Bryce, L. M. Goldenberg, A. Beeby, V. Khodorkovsky, L. Shapiro, A. Niemz, A. O. Cuello, V. Rotello, J. Mater. Chem. 1998, 8, 71-76.
8. [5a] J. Llacay, J. Veciana, J. Vidal-Gancedo, J. L. Bourdelande, R. González-Moreno, C. Rovira, J. Org. Chem. 1998, 63, 5201-5210.
9. [5b] K. B. Simonsen, V. V. Konovalov, T. A. Konovalova, T. Kawai, M. P. Cava, L. D. Kispert, R. M. Metzger, J. Becher, J. Chem. Soc., Perkin Trans. 2 1999, 657-665.
10. [6a] L. M. Goldenberg, J. Y. Becker, O. Paz-Tal Levi, V. Y. Khodorkovsky, M. R. Bryce, M. C. Petty, J. Chem. Soc., Chem. Commun. 1995, 475-476.
11. [6b] L. M. Goldenberg, J. Y. Becker, O. Paz-Tal Levi, V. Y. Khodorkovsky, L. M. Shapiro, M. R. Bryce, J. P. Cresswell, M. C. Petty, J. Mater. Chem. 1997, 7, 901-907.
12. [6c] R. Andreu, I. Malfant, P. G. Lacroix, P. Cassoux, Eur. J. Org. Chem. 2000, 737-741.
13. [6d] For a related BEDT-TTF derivative bearing a pyridyl substituent see: W. Xu, D. Zhang, H. Li, D. Zhu, J. Mater. Chem. 1999, 9, 1245-1249.
14. [7a] K. B. Simonsen, K. Zong, R. D. Rogers, M. P. Cava, J. Becher, J. Org. Chem. 1997, 62, 679-686.
15. [7b] K. B. Simonsen, N. Thorup, M. P. Cava, J. Becher, Chem. Commun. 1998, 901-902.
16. [7c] M. B. Nielsen, J. G. Hansen, J. Becher, Eur. J. Org. Chem. 1999, 2807-2815.
17. A. J. Moore, M. R. Bryce, A. S. Batsanov, J. C. Cole, J. A. K. Howard, Synthesis 1995, 675-682.
18. V. E. Kampar, Russ. Chem. Rev. 1982, 51, 107-128.
19. For the analogous stannylation of TTF see: M. Iyoda, Y. Kuwatani, N. Ueno, M. Oda, J. Chem. Soc., Chem. Commun. 1992, 158-159.
20. A. T. Amos, B. L. Burrows, Adv. Quantum Chem. 1973, 7, 289-313.
21. E. Aqad, A. Ellern, L. Shapiro, V. Khodorkovsky, Tetrahedron Lett. 2000, 41, 2983-2986.
22. J. B. Torrance, Acc. Chem. Res. 1979, 12, 79-86.
23. T. J. Kistenmacher, T. J. Emge, A. N. Bloch, D. O. Cowan, Acta Crystallogr., Sect. B 1982, 38, 1193-1199.
24. D. A. Clemente, A. Marzotto, J. Mater. Chem. 1996, 6, 941-946.
25. [16a] A. J. Moore, M. R. Bryce, A. S. Batsanov, J. N. Heaton, C. W. Lehmann, J. A. K. Howard, N. Robertson, A. E. Underhill, I. F. Perepichka, J. Mater. Chem. 1998, 5, 1541-1550, and references therein.
26. [16b] K. Heuzé, M. Fourmigué, P. Batail, J. Mater. Chem. 1999, 9, 2372-2379.