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
(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 CrossRefCAS.
Reviews:
(a) M. Narita and C. V. Pittman, Synthesis, 1976, 489 CrossRefCAS;
(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 CrossRefCAS.
R. Gompper, H.-U. Wagner and E. Kutter, Chem. Ber., 1968, 101, 4123 CAS.
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 CrossRefCAS.
(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 CrossRefCAS.
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.
M. Guillemet, J. M. Raoul, F. Pellé, A. Robert and M. Baudy-Floc'h, J. Mater. Chem., 1995, 5, 35 RSC.
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 CrossRefCAS.
(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 CrossRefCAS;
(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.
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.
R. Mayer and B. Gebhardt, Chem. Ber., 1964, 97, 1298 CAS.
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.
J. P. Ferraris, T. O. Poehler, A. N. Bloch and D. O. Cowan, Tetrahedron Lett., 1973, 2553 CrossRefCAS.
G. Steimecke, H. Sieler, R. Kirmse and E. Hoyer, Phosphorus Sulfur Relat. Elem., 1979, 7, 49 Search PubMed.
L. R. Melby, H. D. Hartzler and W. A. Sheppard, J. Org. Chem., 1974, 39, 3608 CrossRefCAS.
(a) W. Lehnert, Tetrahedron Lett., 1970, 4723 CrossRefCAS;
(b) W. Lehnert, Synthesis, 1974, 667 CrossRefCAS.
T. Sugimoto, H. Awaji, I. Sugimoto, Y. Misaki, T. Kawase, S. Yoneda, Z. Yoshida, T. Kobayashi and H. Anzai, Chem. Mater., 1989, 1, 535 CrossRefCAS.
A. J. Moore and M. R. Bryce, Tetrahedron Lett., 1992, 33, 1373 CrossRefCAS.
A. Aumüller and S. Hünig, Angew. Chem., Int. Ed. Engl., 1984, 23, 447 CrossRef.
B. J. Adger, C. Barrett, J. Brennan, M. A. McKervey and R. W. Murray, J. Chem. Soc., Chem. Commun., 1991, 1553 RSC.
B. J. Adger, C. Barrett, J. Brennan, P. McGuigan, M. A. McKervey and B. Tarbit, J. Chem. Soc., Chem. Commun., 1993, 1220 RSC.
B. Golding, G. Kennedy and W. P. Watson, Tetrahedron Lett., 1988, 29, 5991 CrossRefCAS.
N. C. Gonella and M. P. Cava, J. Org. Chem., 1979, 44, 930 CrossRefCAS.
(a) Z. Yoshida, T. Kawase, H. Awaji, I. Sugimoto, T. Sugimoto and S. Yoneda, Tetrahedron Lett., 1983, 24, 3469 CrossRefCAS;
(b) Z. Yoshida, H. Awaji and T. Sugimoto, Tetrahedron Lett., 1984, 25, 4227 CrossRefCAS;
(c) T. K. Hansen, M. V. Lakshmikantham, M. P. Cava, R. M. Metzger and J. Becher, J. Org. Chem., 1991, 56, 2720 CrossRefCAS;
(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 CrossRefCAS;
(g) D. Lorcy, R. Carlier, A. Robert, A. Tallec, P. Le Magueres and L. Ouahab, J. Org. Chem., 1995, 60, 2443 CrossRefCAS;
(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 CrossRefCAS;
(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.
(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.
(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 CrossRefCAS;
(c) A. S. Benahmed-Gasmi, P. Frère, B. Garrigues, A. Gorgues, M. Jubault, R. Carlier and F. Texier, Tetrahedron Lett., 1992, 33, 6457 CrossRefCAS;
(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 CrossRefCAS.
S. Kugimiya, T. Lazarak, M. Blanchard-Desce and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1991, 1179 RSC.
Compound 11d was prepared by modification of the literature
preparation for compound 11b, ref. 18, using tributylphosphine
instead of triphenylphosphine.
(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 CrossRefCAS.
(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.
(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.
A. Kenwright,
University of Durham, unpublished
results.
(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 CrossRefCAS.
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 CrossRefCAS.
N.-H. Dung and J. Etienne, Acta Crystallogr., Sect. B, 1978, 34, 683 CrossRef.
H. Hopf, M. Kreutzer and P. G. Jones, Angew. Chem., Int. Ed. Engl., 1991, 30, 1127 CrossRef.
(a) A. Gavezzotti, J. Am. Chem. Soc., 1983, 105, 5220 CrossRefCAS;
(b) G. Filippini and A. Gavezzotti, Acta Crystallogr., Sect. B, 1993, 49, 868 CrossRef.
J. L. Oudar, J. Chem. Phys., 1977, 67, 446 CrossRefCAS.
S. Brasselet and J. Zyss, Int. J. Nonlinear Opt. Phys., 1996, 5, 671 Search PubMed.
(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 CrossRefCAS;
(d) R. O. Jones and O. Gunnarsson, Rev. Mod. Phys., 1990, 61, 689 CrossRefCAS.
(a) J. Andzelm, C. Sosa and R. A. Eades, J. Phys. Chem., 1993, 97, 4664 CrossRefCAS;
(b) C. W. Bauschlicher Jr., Chem. Phys. Lett., 1995, 246, 40 CrossRefCAS;
(c) G. Rauhut and P. Pulay, J. Phys. Chem., 1995, 99, 3093 CrossRefCAS;
(d) J. S. Kwiatkowski and J. Leszczynski, J. Phys. Chem., 1996, 100, 941 CrossRefCAS;
(e) J. A. C. Scheiner, J. Baker and J. W. Andzelm, J. Comput. Chem., 1997, 18, 775 CrossRefCAS;
(f) V. Barone, C. Adamo and F. Mele, Chem. Phys. Lett., 1996, 246, 290 CrossRef.
G. M. Sheldrick,
SHELXTL, Version 5, Siemens Analytical X-Ray
Instruments Inc., Madison, USA,
1995.
TEXSAN: Single Crystal Structure Analysis Software, Version 5.0,
Molecular Structure Corporation, TX, USA,
1989.
E. A. Guggenheim, Trans. Faraday Soc., 1949, 45, 203 RSC.
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.
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 CrossRefCAS;
(b) J. P. Perdew, Phys. Rev. B, 1986, 33, 8822 CrossRef.
P. C. Hariharan and J. A. Pople, Chem. Phys. Lett., 1972, 16, 217 CrossRefCAS.
H. B. Schlegel, J. Comput. Chem., 1982, 3, 214 CrossRefCAS.
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