New 1,3-dithiol-2-ylidene donor–π–acceptor chromophores with intramolecular charge-transfer properties, and related donor–π–donor molecules: synthesis, electrochemistry, X-ray crystal structures, non-linear optical properties and theoretical calculations

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Adrian J. Moore, Martin R. Bryce, Andrei S. Batsanov, Andrew Green, Judith A. K. Howard, Anthony Mckervey, Peter Mcguigan, Isabelle Ledoux, Enrique Ortí, Rafael Viruela, Pedro M. Viruela and Brian Tarbit


Abstract


References

  1. (a) Reviews: Nonlinear Optical Properties of Organic Molecules and Crystals, ed. D. S. Chemla and J. Zyss, Academic Press, Boston, 1987 Search PubMed; (b) P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991 Search PubMed; (c) Molecular Nonlinear Optics: Materials, Physics and Devices, ed. J. Zyss, Academic Press, Boston, 1994 Search PubMed; (d) R. G. Denning, J. Mater. Chem., 1995, 5, 365 RSC; (e) T. J. Marks and M. A. Ratner, Angew. Chem., Int. Ed. Engl., 1995, 34, 155 CrossRef CAS.
  2. Reviews: (a) M. Narita and C. V. Pittman, Synthesis, 1976, 489 CrossRef CAS; (b) A. Krief, Tetrahedron, 1986, 42, 1237 CrossRef; (c) G. Schukat, A. M. Richter and E. Fanghänel, Sulfur Rep., 1987, 7, 155 Search PubMed; (d) G. Schukat and E. Fanghänel, Sulfur Rep., 1993, 13, 254 Search PubMed; (e) T. K. Hansen and J. Becher, Adv. Mater., 1993, 5, 288 CrossRef CAS.
  3. R. Gompper, H.-U. Wagner and E. Kutter, Chem. Ber., 1968, 101, 4123 CAS.
  4. H. E. Katz, K. D. Singer, J. E. Sohn, C. W. Dirk, L. A. King and H. M. Gordon, J. Am. Chem. Soc., 1987, 109, 6561 CrossRef CAS.
  5. (a) M. Blanchard-Desce, I. Ledoux, J.-M. Lehn, J. Malthete and J. Zyss, J. Chem. Soc., Chem. Commun., 1988, 737 RSC; (b) M. Barzoukas, M. Blanchard-Desce, D. Josse, J.-M. Lehn and J. Zyss, Chem. Phys., 1989, 133, 323 CrossRef CAS.
  6. A. K.-Y. Jen, V. P. Rao, K. J. Drost, K. Y. Wong and M. P. Cava, J. Chem. Soc., Chem. Commun., 1994, 2057 RSC.
  7. M. Guillemet, J. M. Raoul, F. Pellé, A. Robert and M. Baudy-Floc'h, J. Mater. Chem., 1995, 5, 35 RSC.
  8. C.-S. Kang, C. Heldmann, H.-J. Winkelhahn, M. Schulze, D. Neher, G. Wegner, R. Wortmann, C. Glania and P. Krämer, Macromolecules, 1994, 27, 6156 CrossRef CAS.
  9. (a) A. I. de Lucas, N. Martín, L. Sanchez, C. Seoane, J. Garín, J. Orduna, R. Alcalá and B. Villacampa, Tetrahedron Lett., 1997, 38, 6107 CrossRef CAS; (b) S. Inoue, Y. Aso and T. Otsubo, Chem. Commun., 1997, 1105 RSC; (c) K. Kondo, T. Fujitani and N. Ohnishi, J. Mater. Chem., 1997, 7, 429 RSC.
  10. For reviews of dicyanomethylene and N-cyanoimine groups in materials chemistry see: (a) S. Hünig, J. Mater. Chem., 1995, 5, 1469 RSC; (b) N. Martín, J. L. Segura and C. Seoane, J. Mater. Chem., 1997, 7, 1661 RSC.
  11. R. Mayer and B. Gebhardt, Chem. Ber., 1964, 97, 1298 CAS.
  12. Reviews: (a) H. Prinzbach and E. Futterer, Adv. Heterocycl. Chem., 1966, 7, 39 CAS; (b) N. Lozac'h and M. Stavaux, Adv. Heterocycl. Chem., 1980, 27, 151 CAS.
  13. J. P. Ferraris, T. O. Poehler, A. N. Bloch and D. O. Cowan, Tetrahedron Lett., 1973, 2553 CrossRef CAS.
  14. G. Steimecke, H. Sieler, R. Kirmse and E. Hoyer, Phosphorus Sulfur Relat. Elem., 1979, 7, 49 Search PubMed.
  15. L. R. Melby, H. D. Hartzler and W. A. Sheppard, J. Org. Chem., 1974, 39, 3608 CrossRef CAS.
  16. (a) W. Lehnert, Tetrahedron Lett., 1970, 4723 CrossRef CAS; (b) W. Lehnert, Synthesis, 1974, 667 CrossRef CAS.
  17. T. Sugimoto, H. Awaji, I. Sugimoto, Y. Misaki, T. Kawase, S. Yoneda, Z. Yoshida, T. Kobayashi and H. Anzai, Chem. Mater., 1989, 1, 535 CrossRef CAS.
  18. A. J. Moore and M. R. Bryce, Tetrahedron Lett., 1992, 33, 1373 CrossRef CAS.
  19. A. Aumüller and S. Hünig, Angew. Chem., Int. Ed. Engl., 1984, 23, 447 CrossRef.
  20. B. J. Adger, C. Barrett, J. Brennan, M. A. McKervey and R. W. Murray, J. Chem. Soc., Chem. Commun., 1991, 1553 RSC.
  21. B. J. Adger, C. Barrett, J. Brennan, P. McGuigan, M. A. McKervey and B. Tarbit, J. Chem. Soc., Chem. Commun., 1993, 1220 RSC.
  22. B. Golding, G. Kennedy and W. P. Watson, Tetrahedron Lett., 1988, 29, 5991 CrossRef CAS.
  23. N. C. Gonella and M. P. Cava, J. Org. Chem., 1979, 44, 930 CrossRef CAS.
  24. (a) Z. Yoshida, T. Kawase, H. Awaji, I. Sugimoto, T. Sugimoto and S. Yoneda, Tetrahedron Lett., 1983, 24, 3469 CrossRef CAS; (b) Z. Yoshida, H. Awaji and T. Sugimoto, Tetrahedron Lett., 1984, 25, 4227 CrossRef CAS; (c) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger and J. Becher, J. Org. Chem., 1991, 56, 2720 CrossRef CAS; (d) A. J. Moore, M. R. Bryce, D. J. Ando and M. B. Hursthouse, J. Chem. Soc., Chem. Commun., 1991, 329 Search PubMed; (e) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava and J. Becher, J. Chem. Soc., Perkin Trans. 1, 1991, 2873 RSC; (f) M. R. Bryce, M. A. Coffin and W. Clegg, J. Org. Chem., 1992, 57, 1696 CrossRef CAS; (g) D. Lorcy, R. Carlier, A. Robert, A. Tallec, P. Le Magueres and L. Ouahab, J. Org. Chem., 1995, 60, 2443 CrossRef CAS; (h) Y. Misaki, T. Ohta, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, J. Mater. Chem., 1995, 5, 1571 RSC; (i) Review; M. R. Bryce, J. Mater. Chem., 1995, 5, 1481 Search PubMed; (j) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead, W. Clegg, F. Gerson and A. Lamprecht, Chem. Mater., 1996, 8, 1182 CrossRef CAS; (k) T.-T. Nguyen, Y. Gouriou, M. Sallé, P. Frère, M. Jubault, A. Gorgues, L. Youpet and A. Riou, Bull. Soc. Chim. Fr., 1996, 133, 301 CAS.
  25. (a) M. R. Bryce, A. J. Moore, M. Hasan, G. J. Ashwell, A. T. Fraser, W. Clegg, M. B. Hursthouse and A. I. Karaulov, Angew. Chem., Int. Ed. Engl., 1990, 29, 1450 CrossRef; (b) J. Dong, K. Yakushi and Y. Yamashita, J. Mater. Chem., 1995, 5, 1735 RSC.
  26. (a) U. Schöberl, J. Salbeck and J. Daub, Adv. Mater., 1992, 4, 41 CrossRef; (b) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. E. Niziurski-Mann, F. Jensen and J. Becher, J. Am. Chem. Soc., 1992, 114, 5035 CrossRef CAS; (c) A. S. Benahmed-Gasmi, P. Frère, B. Garrigues, A. Gorgues, M. Jubault, R. Carlier and F. Texier, Tetrahedron Lett., 1992, 33, 6457 CrossRef CAS; (d) A. Benahmed-Gasmi, P. Frère, E. H. Elandaloussi, J. Roncali, J. Orduna, J. Garín, M. Jubault, A. Riou and A. Gorgues, Chem. Mater., 1996, 8, 2291 CrossRef CAS.
  27. S. Kugimiya, T. Lazarak, M. Blanchard-Desce and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1991, 1179 RSC.
  28. Compound 11d was prepared by modification of the literature preparation for compound 11b, ref. 18, using tributylphosphine instead of triphenylphosphine.
  29. (a) P. Frère, A. Belyasmine, A. Gorgues, G. Duguay, K. Boubekeur and P. Batail, Tetrahedron Lett., 1993, 34, 4519 CrossRef; (b) P. Frère, A. Belyasmine, Y. Gouriou, M. Jubault, A. Gorgues, G. Duguay, S. Wood, C. D. Reynolds and M. R. Bryce, Bull. Soc. Chim. Fr., 1995, 132, 975 CAS; (c) M. R. Bryce, M. Chalton, A. S. Batsanov, C. W. Lehmann and J. A. K. Howard, J. Chem. Soc., Perkin Trans. 2, 1996, 2367 RSC; (d) P. Leriche, A. Belyasmine, M. Sallé, P. Frère, A. Gorgues, A. Riou, M. Jubault, J. Orduna and J. Garín, Tetrahedron Lett., 1996, 37, 8861 CrossRef CAS.
  30. (a) Y. Mollier, F. Terrier and N. Lozach, Bull. Soc. Chim. Fr., 1964, 1778 CAS; (b) R. Pinel and Y. Mollier, Bull. Soc. Chim. Fr., 1972, 1385 CAS; (c) R. Pinel, Y. Mollier, J. P. de Barbeyarac and G. Pfister-Guillouzo, C. R. Seances Acad. Sci., Ser. C, 1972, 275, 909 Search PubMed; (d) R. Pinel, Y. Mollier, E. C. Liaguno and I. C. Paul, J. Chem. Soc., Chem. Commun., 1971, 1352 RSC.
  31. (a) S. Bezzi, M. Mammi and C. Garbuglio, Nature, 1958, 182, 247 CAS; (b) L. Hansen and A. Hordvik, Acta Chem. Scand., 1973, 27, 411 CAS; (c) Review: C. T. Pedersen, Sulfur Rep., 1980, 1, 1 Search PubMed.
  32. A. Kenwright, University of Durham, unpublished results.
  33. (a) R. H. Baughman, B. E. Kohler, I. J. Levy and C. Spangler, Synth. Met., 1985, 11, 37 CAS; (b) A. Kiehl, A. Eberhardt, M. Adam, V. Enkelmann and K. Müllen, Angew. Chem., Int. Ed. Engl., 1992, 31, 1588 CrossRef; (c) T. Hamanaka, T. Mitsui, T. Ashida and M. Kakudo, Acta Crystallogr., Sect. B, 1972, 28, 214 CrossRef CAS.
  34. S. R. Marder, J. W. Perry, B. G. Tieman, C. B. Gorman, S. Gilmour, S. L. Biddle and G. Bourhill, J. Am. Chem. Soc., 1993, 115, 2524 CrossRef CAS.
  35. N.-H. Dung and J. Etienne, Acta Crystallogr., Sect. B, 1978, 34, 683 CrossRef.
  36. H. Hopf, M. Kreutzer and P. G. Jones, Angew. Chem., Int. Ed. Engl., 1991, 30, 1127 CrossRef.
  37. (a) A. Gavezzotti, J. Am. Chem. Soc., 1983, 105, 5220 CrossRef CAS; (b) G. Filippini and A. Gavezzotti, Acta Crystallogr., Sect. B, 1993, 49, 868 CrossRef.
  38. J. L. Oudar, J. Chem. Phys., 1977, 67, 446 CrossRef CAS.
  39. S. Brasselet and J. Zyss, Int. J. Nonlinear Opt. Phys., 1996, 5, 671 Search PubMed.
  40. (a) R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989 Search PubMed; (b) M. Levy, Proc. Natl. Acad. Sci. USA, 1979, 76, 6062 CAS; (c) T. Ziegler, Chem. Rev., 1991, 91, 651 CrossRef CAS; (d) R. O. Jones and O. Gunnarsson, Rev. Mod. Phys., 1990, 61, 689 CrossRef CAS.
  41. (a) J. Andzelm, C. Sosa and R. A. Eades, J. Phys. Chem., 1993, 97, 4664 CrossRef CAS; (b) C. W. Bauschlicher Jr., Chem. Phys. Lett., 1995, 246, 40 CrossRef CAS; (c) G. Rauhut and P. Pulay, J. Phys. Chem., 1995, 99, 3093 CrossRef CAS; (d) J. S. Kwiatkowski and J. Leszczynski, J. Phys. Chem., 1996, 100, 941 CrossRef CAS; (e) J. A. C. Scheiner, J. Baker and J. W. Andzelm, J. Comput. Chem., 1997, 18, 775 CrossRef CAS; (f) V. Barone, C. Adamo and F. Mele, Chem. Phys. Lett., 1996, 246, 290 CrossRef.
  42. G. M. Sheldrick, SHELXTL, Version 5, Siemens Analytical X-Ray Instruments Inc., Madison, USA, 1995.
  43. TEXSAN: Single Crystal Structure Analysis Software, Version 5.0, Molecular Structure Corporation, TX, USA, 1989.
  44. E. A. Guggenheim, Trans. Faraday Soc., 1949, 45, 203 RSC.
  45. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stevanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision D.3, Gaussian Inc., Pittsburgh, PA, 1995.
  46. The B3P86 functional consists of Becke's three-parameter hybrid functional,46a which is a hybrid of Hartree Fock exchange with local and gradient-corrected exchange and correlation terms, with the nonlocal correlation provided by the ‘Perdew 86’46b expression. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648 CrossRef CAS; (b) J. P. Perdew, Phys. Rev. B, 1986, 33, 8822 CrossRef.
  47. P. C. Hariharan and J. A. Pople, Chem. Phys. Lett., 1972, 16, 217 CrossRef CAS.
  48. H. B. Schlegel, J. Comput. Chem., 1982, 3, 214 CrossRef CAS.
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