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

Journal of Materials Chemistry

Volumn 8, Issue 5, 1998, Pages 1173-1184

  Moore, Adrian J ^a   Bryce, Martin R ^a   Batsanov, Andrei S ^a   Green, Andrew ^a   Howard, Judith A K ^a   McKervey, M Anthony ^b   McGuigan, Peter ^b   Ledoux, Isabelle ^c   Ortí, Enrique ^d   Viruela, Rafael ^d   Viruela, Pedro M ^d   Tarbit, Brian ^e,f  

^a DURHAM UNIVERSITY   (United Kingdom)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^c ORANGE LABS   (France)

^d UNIVERSITY OF VALENCIA   (Spain)

^e Great Lakes Chemical (Europe) Ltd   (United Kingdom)

^f Seal Sands Chemicals Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000627409     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708078f     Document Type: Article

References (96)

1. Reviews: (a) Nonlinear Optical Properties of Organic Molecules and Crystals, ed. D. S. Chemla and J. Zyss, Academic Press, Boston, 1987;
2. (b) P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991;
3. (c) Molecular Nonlinear Optics: Materials, Physics and Devices, ed. J. Zyss, Academic Press, Boston, 1994;
4. (d) R. G. Denning, J. Mater. Chem., 1995; 5, 365;
5. (e) T. J. Marks and M. A. Ratner, Angew. Chem., Int. Ed. Engl., 1995, 3-4, 155.
6. Reviews: (a) M. Narita and C. V. Pittman, Synthesis, 1976, 489;
7. (b) A. Krief, Tetrahedron, 1986, 42, 1237;
8. (c) G. Schukat, A. M. Richter and E. Fanghänel, Sulfur Rep., 1987, 7, 155;
9. (d) G. Schukat and E. Fanghänel, Sulfur Rep., 1993, 13, 254;
10. (e) T. K. Hansen and J. Becher, Adv. Mater., 1993, 5, 288.
11. R. Gompper, H.-U. Wagner and E. Kutter, Chem. Ber., 1968, 101, 4123.
12. 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.
13. (a) M. Blanchard-Desce, I. Ledoux, J.-M. Lehn, J. Malthete and J. Zyss, J. Chem. Soc., Chem. Commun., 1988, 737;
14. (b) M. Barzoukas, M. Blanchard-Desce, D. Josse, J.-M. Lehn and J. Zyss, Chem. Phys., 1989, 133, 323.
15. A. K.-Y. Jen, V. P. Rao, K. J. Drost, K. Y. Wong and M. P. Cava, J. Chem. Soc., Chem. Commun., 1994, 2057.
16. M. Guillemet, J. M. Raoul, F. Pellé, A. Robert and M. Baudy-Floc'h, J. Mater. Chem., 1995, 5, 35.
17. 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.
18. (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;
19. (b) S. Inoue, Y. Aso and T. Otsubo, Chem. Commun., 1997, 1105;
20. (c) K. Kondo, T. Fujitani and N. Ohnishi, J. Mater. Chem., 1997, 7, 429.
21. For reviews of dicyanomethylene and N-cyanoimine groups in materials chemistry see: (a) S. Hünig, J. Mater. Chem., 1995, 5, 1469;
22. (b) N. Martín, J. L. Segura and C. Seoane, J. Mater. Chem., 1997, 7, 1661.
23. R. Mayer and B. Gebhardt, Chem. Ber., 1964, 97, 1298.
24. Reviews: (a) H. Prinzbach and E. Futterer, Adv. Heterocycl. Chem., 1966, 7, 39;
25. (b) N. Lozac'h and M. Stavaux, Adv. Heterocycl. Chem., 1980, 27, 151.
26. J. P. Ferraris, T. O. Poehler, A. N. Bloch and D. O. Cowan, Tetrahedron Lett., 1973, 2553.
27. G. Steimecke, H. Sieler, R. Kirmse and E. Hoyer, Phosphorus Sulfur Relat. Elem., 1979, 7, 49.
28. L. R. Melby, H. D. Hartzier and W. A. Sheppard, J. Org. Chem., 1974, 39, 3608.
29. (a) W. Lehnert, Tetrahedron Lett., 1970, 4723;
30. (b) W. Lehnert, Synthesis, 1974, 667.
31. T. Sugimoto, H. Awaji, I. Sugimoto, Y. Misaki, T. Kawase, S. Yoneda, Z. Yoshida, T. Kobayashi and H. Anzai, Chem. Mater., 1989, 1, 535.
32. A. J. Moore and M. R. Bryce, Tetrahedron Lett., 1992, 33, 1373.
33. A. Aumüller and S. Hünig, Angew. Chem., Int. Ed. Engl., 1984, 23, 447.
34. B. J. Adger, C. Barrett, J. Brennan, M. A. McKervey and R. W. Murray, J. Chem. Soc., Chem. Commun., 1991, 1553.
35. B. J. Adger, C. Barrett, J. Brennan, P. McGuigan, M. A. McKervey and B. Tarbit, J. Chem. Soc., Chem. Commun., 1993, 1220.
36. B. Golding, G. Kennedy and W. P. Watson, Tetrahedron Lett., 1988, 29, 5991.
37. N. C. Gonella and M. P. Cava, J. Org. Chem., 1979, 44, 930.
38. (a) Z. Yoshida, T. Kawase, H. Awaji, I. Sugimoto, T. Sugimoto and S. Yoneda, Tetrahedron Lett., 1983, 24, 3469;
39. (b) Z. Yoshida, H. Awaji and T. Sugimoto, Tetrahedron Lett., 1984, 25, 4227;
40. (c) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger and J. Becher, J. Org. Chem., 1991, 56, 2720;
41. (d) A. J. Moore, M. R. Bryce, D. J. Ando and M. B. Hursthouse, J. Chem. Soc., Chem. Commun., 1991, 329;
42. (e) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava and J. Becher, J. Chem. Soc., Perkin Trans. 1, 1991, 2873;
43. (f) M. R. Bryce, M. A. Coffin and W. Clegg, J. Org. Chem., 1992, 57, 1696;
44. (g) D. Lorcy, R. Carlier, A. Robert, A. Tallec, P. Le Magueres and L. Ouahab, J. Org. Chem., 1995, 60, 2443;
45. (h) Y. Misaki, T. Ohta, N. Higuchi, H. Fujiwara, T. Yamabe, T. Mori, H. Mori and S. Tanaka, J. Mater. Chem., 1995, 5, 1571;
46. (i) Review; M. R. Bryce, J. Mater. Chem., 1995, 5, 1481;
47. (j) M. R. Bryce, A. J. Moore, B. K. Tanner, R. Whitehead, W. Clegg, F. Gerson and A. Lamprecht, Chem. Mater., 1996, 8, 1182;
48. (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.
49. (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;
50. (b) J. Dong, K. Yakushi and Y. Yamashita, J. Mater. Chem., 1995, 5, 1735.
51. (a) U. Schöberl, J. Salbeck and J. Daub, Adv. Mater., 1992, 4, 41;
52. (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;
53. (c) A. S. Benahmed-Gasmi, P. Frère, B. Garrigues, A. Gorgues, M. Jubault, R. Carlier and F. Texier, Tetrahedron Lett., 1992, 33, 6457;
54. (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.
55. S. Kugimiya, T. Lazarak, M. Blanchard-Desce and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1991, 1179.
56. Compound 11d was prepared by modification of the literature preparation for compound 11b, ref. 18, using tributylphosphine instead of triphenylphosphine.
57. (a) P. Frère, A. Belyasmine, A. Gorgues, G. Duguay, K. Boubekeur and P. Batail, Tetrahedron Lett., 1993, 34, 4519;
58. (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;
59. (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;
60. (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.
61. (a) Y. Mollier, F. Terrier and N. Lozach, Bull. Soc. Chim. Fr., 1964, 1778;
62. (b) R. Pinel and Y. Mollier, Bull. Soc. Chim. Fr., 1972, 1385;
63. (c) R. Pinel, Y. Mollier, J. P. de Barbeyarac and G. Pfister-Guillouzo, C. R. Seances Acad. Sci., Ser. C, 1972, 275, 909;
64. (d) R. Pinel, Y. Mollier, E. C. Liaguno and I. C. Paul, J. Chem. Soc., Chem. Commun., 1971, 1352.
65. (a) S. Bezzi, M. Mammi and C. Garbuglio, Nature, 1958, 182, 247;
66. (b) L. Hansen and A. Hordvik, Acta Chem. Scand., 1973, 27, 411;
67. (c) Review: C. T. Pedersen, Sulfur Rep., 1980, 1, 1.
68. A. Kenwright, University of Durham, unpublished results.
69. (a) R. H. Baughman, B. E. Kohler, I. J. Levy and C. Spangler, Synth. Met., 1985, 11, 37;
70. (b) A. Kiehl, A. Eberhardt, M. Adam, V. Enkelmann and K. Müllen, Angew. Chem., Int. Ed. Engl., 1992, 31, 1588;
71. (c) T. Hamanaka, T. Mitsui, T. Ashida and M. Kakudo, Acta Crystallogr., Sect. B, 1972, 28, 214.
72. 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.
73. N.-H. Dung and J. Etienne, Acta Crystallogr., Sect. B, 1978, 34, 683.
74. H. Hopf, M. Kreutzer and P. G. Jones, Angew. Chem., Int. Ed. Engl., 1991, 30, 1127.
75. (a) A. Gavezzotti, J. Am. Chem. Soc., 1983, 105, 5220;
76. (b) G. Filippini and A. Gavezzotti, Acta Crystallogr., Sect. B, 1993, 49, 868.
77. J. L. Oudar, J. Chem. Phys., 1977, 67, 446.
78. S. Brasselet and J. Zyss, Int. J. Nonlinear Opt. Phys., 1996, 5, 671.
79. (a) R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989;
80. (b) M. Levy, Proc. Natl. Acad. Sci. USA, 1979, 76, 6062;
81. (c) T. Ziegler, Chem. Rev., 1991, 91, 651;
82. (d) R. O. Jones and O. Gunnarsson, Rev. Mod. Phys., 1990, 61, 689.
83. (a) J. Andzelm, C. Sosa and R. A. Eades, J. Phys. Chem., 1993, 97, 4664;
84. (b) C. W. Bauschlicher Jr., Chem. Phys. Lett., 1995, 246, 40;
85. (c) G. Rauhut and P. Pulay, J. Phys. Chem., 1995; 99, 3093;
86. (d) J. S. Kwiatkowski and J. Leszczynski, J. Phys. Chem., 1996, 100, 941;
87. (e) J. A. C. Scheiner, J. Baker and J. W. Andzelm, J. Comput. Chem., 1997, 18, 775;
88. (f) V. Barone, C. Adamo and F. Mele, Chem. Phys. Lett., 1996, 246, 290.
89. G. M. Sheldrick, SHELXTL, Version 5, Siemens Analytical X-Ray Instruments Inc., Madison, USA, 1995.
90. TEXSAN: Single Crystal Structure Analysis Software, Version 5.0, Molecular Structure Corporation, TX, USA, 1989.
91. E. A. Guggenheim, Trans. Faraday Soc., 1949, 45, 203.
92. 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.
93. 46b expression. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648;
94. (b) J. P. Perdew, Phys. Rev. B, 1986, 33, 8822.
95. P. C. Hariharan and J. A. Pople, Chem. Phys. Lett., 1972, 16, 217.
96. H. B. Schlegel, J. Comput. Chem., 1982, 3, 214.