Synthesis and X-ray crystal structure of a vinylogue of tetramethyltetraselenafulvalene

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Martin R. Bryce, Antony Chesney, Shimon Yoshida, Adrian J. Moore, Andrei S. Batsanov and Judith A. K. Howard


Abstract

Efficient syntheses of 2,2′-ethanediylidenebis(4,5-dimethyl-2 H-1,3-diselenole) 14 and the 1,3-dithiole analogue 16 are described. Cyclic voltammetry establishes that they are efficient π-electron donors. The molecular structures of 14 and 16 have been determined by single crystal X-ray analysis: the crystals are isomorphous and the molecules form planar layers parallel to the crystallographic (1 0 2) plane.


References

  1. (a) J. R. Ferraro and J. M. Williams, Introduction to Synthetic Electrical Conductors, Academic Press, London, 1987 Search PubMed; (b) M. R. Bryce, Chem. Soc. Rev., 1991, 20, 355 RSC; (c) A. E. Underhill, J. Mater. Chem., 1992, 2, 1 RSC; (d) J. Mater. Chem., Special Issue on Molecular Conductors, 1995, 5, 1469 Search PubMed.
  2. (a) J. P. Ferraris, D. Cowan, V. Walatka and J. H. Perlstein, J. Am. Chem. Soc., 1973, 95, 948 CrossRef CAS; (b) L. B. Coleman, M. J. Cohen, D. J. Sandman, F. G. Yamagishi, A. F. Garito and A. J. Heeger, Solid State Commun., 1973, 12, 1125 CrossRef CAS.
  3. (a) K. Bechgaard, K. Carneiro, F. B. Rasmussen, M. Olsen, G. Rindorf, C. S. Jacobsen, H. J. Pedersen and J. C. Scott, J. Am. Chem. Soc., 1981, 103, 2440 CrossRef CAS; (b) K. Bechgaard and D. Jérome, Sci. Am., 1982, 247, 50 Search PubMed.
  4. (a) A. M. Kini, U. Geiser, H. H. Wang, K. D. Carlson, J. M. Williams, W. K. Kwok, K. G. Vandervoot, J. E. Thompson, D. L. Stupka, D. Jung and M.-H. Whangbo, Inorg. Chem., 1990, 29, 2555 CrossRef CAS; (b) J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini and M.-H. Whangbo, Organic Superconductors (including Fullerenes), Prentice Hall, New Jersey, 1992 Search PubMed.
  5. S. Roth, One-Dimensional Metals, VCH, Weinheim, 1995 Search PubMed.
  6. (a) Z. Yoshida, T. Kawasi, H. Awaji, I. Sugimoto, T. Sugimoto and S. Yoneda, Tetrahedron Lett., 1983, 24, 3469 CrossRef CAS; (b) T. Sugimoto, H. Awaji, I. Sugimoto, Y. Misaki, T. Kawase, S. Yoneda and Z. Yoshida, Chem. Mater., 1989, 1, 535 CrossRef CAS; (c) V. Yu Khodorkovskii, L. N. Veselova and O. Ya. Neiland, Khim. Geterotsikl. Soedin., 1990, 130 (Chem. Abstr., 1990, 113, 22868) Search PubMed; (d) A. J. Moore, M. R. Bryce, D. J. Ando and M. B. Hursthouse, J. Chem. Soc., Chem. Commun., 1991, 320 RSC; (e) T. K. Hansen, M. V. Lakshimikantham, M. P. Cava, R. M. Metzger and J. Becher, J. Org. Chem., 1991, 56, 2720 CrossRef CAS; (f) M. R. Bryce, M. A. Coffin and W. Clegg, J. Org. Chem., 1992, 57, 1696 CrossRef CAS; (g) M. Sallé, M. Jubault, A. Gorgues, K. Boubekeur, M. Fourmigué, P. Batail and E. Canadell, Chem. Mater., 1993, 5, 1196 CrossRef CAS; (h) Y. Misaki, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Angew. Chem., Int. Ed. Engl., 1995, 34, 1222 CrossRef CAS; (i) Y. Misaki, T. Ohta, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, J. Mater. Chem., 1995, 5, 1571 RSC; (j) D. Lorcy, R. Carlier, A. Robert, A. Tallec, P. Le Magueres and L. Ouahab, J. Org. Chem., 1995, 60, 1443; (k) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead, W. Clegg, F. Gerson, A. Lamprecht and S. Pfenninger, Chem. Mater., 1996, 8, 1182 CrossRef CAS.
  7. For reviews on vinylogous TTF donors see: (a) Z. Yoshida and T. Sugimoto, Angew. Chem., Int. Ed. Engl., 1988, 27, 1573 CrossRef; (b) M. R. Bryce, J. Mater. Chem., 1995, 5, 1481 RSC.
  8. Y. Misaki, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, Chem. Commun., 1996, 363 RSC.
  9. K. Bechgaard, D. O. Cowan, A. N. Bloch and L. Henriksen, J. Org. Chem., 1975, 40, 746 CrossRef CAS.
  10. A. J. Moore and M. R. Bryce, unpublished observations. See also references 6(a) and 6(b) in which tributylphosphine is used exclusively in similar reactions.
  11. K. Akiba, K. Ishikawa and N. Inamoto, Bull. Chem. Soc. Jpn., 1978, 51, 2674 CAS; A. J. Moore and M. R. Bryce, J. Chem. Soc., Perkin Trans. 1, 1991, 157 RSC.
  12. (a) A. Mhanni, L. Ouahab, D. Grandjean, J. Amouroux and J. M. Fabre, Acta Crystallogr., Sect. C, 1991, 47, 1980 CrossRef; (b) S. Triki, L. Quahab, D. Grandjean, J. Amouroux and J. M. Fabre, Acta Crystallogr., Sect. C, 1991, 47, 1941 CrossRef.
  13. L. Pauling, The Nature of the Chemical Bond, 3rd edn., Cornell University Press, Ithaca, 1960 Search PubMed.
  14. G. Filippini and A. Gavezzotti, Acta Crystallogr., Sect. B, 1993, 49, 868 CrossRef.
  15. T. Miller and B. Bedeson, Adv. Atom. Mol. Phys., 1977, 13, 1 Search PubMed.
  16. E. M. Engler, F. B. Kaufman, D. C. Green, C. E. Klots and R. N. Compton, J. Am. Chem. Soc., 1975, 97, 2921 CrossRef CAS.
  17. E. M. Engler, V. V. Patel, J. R. Anderson, R. R. Schumaker and A. A. Fukushima, J. Am. Chem. Soc., 1978, 100, 3769 CrossRef CAS.
  18. General details: M. R. Bryce, A. Chesney, A. K. Lay, A. S. Batsanov and J. A. K. Howard, J. Chem. Soc., Perkin Trans. 1, 1996, 2451 Search PubMed.
  19. G. M. Sheldrick, SHELXTL, ver. 5/VMS, Siemens Analytical X-Ray Instruments Inc., Madison, Wisconsin, USA, 1995.
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