Synthesis and non-linear properties of conjugated poly-unsaturated amino carbene complexes

Journal of Organometallic Chemistry

Volumn 583, Issue 1-2, 1999, Pages 111-119

  Licandro, Emanuela ^a   Maiorana, Stefano ^a   Papagni, Antonio ^a   Hellier, Paul ^a   Capella, Laura ^a   Persoons, Andre ^b   Houbrechts, Stephan ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Fischer type carbene complexes; NLO properties; Poly unsaturated amides; Poly unsaturated aminocarbene complexes

Indexed keywords

EID: 0000538384     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(99)00122-9     Document Type: Article

References (44)

1. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
2. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
3. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
4. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
5. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
6. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
7. For general reading on NLO: (a) N.J. Long, Angew. Chem. Int. Ed. Engl., 34 (1995) 21. (b) W. Nie, Adv. Mater., 5 (1993) 520. (c) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev., 94. (d) R.W. Munn, C.N. Ironside, Principles and Applications of Nonlinear Optical Materials, Chapman & Hall, London (1993). (e) P.N. Prasad, D.J. Williams, Introduction to Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York (1991). (f) B.F. Levine, C.G. Bethea, J. Chem. Phys., 63 (1975) 2667. J. Zyss, Molecular Nonlinear Optics, Academic Press (1994), and references cited therein.
8. (a) J.L. Oudar, D.S.J. Chemla, J. Chem. Phys., 66 (1977) 2664.
9. (b) E. Hendrickx, K. Clays, A. Persoons, C. Dehu, J.L. Bredas, J. Am. Chem Soc., 117 (1995) 3547.
10. (a) C. Lambert, S. Stadler, G. Bourhill, C. Bräuchle, Angew. Chem. Int. Ed. Engl., 35 (1996) 644.
11. (b) A. Bahl, W. Grahn, S. Stadler, F. Feiner, G. Bourhill, C. Bräuchle, Angew. Chem. Int. Ed. Engl., 34 (1995) 1485.
12. (c) L.T. Chen, W. Tam, S.R. Marder, A.E. Steigman, G. Rikken, C.W. Spangler, J. Phys. Chem., 95 (1991) 10643.
13. (d) A. Abbotto, S. Bradamante, A. Facchetti, G.A. Pagani, J. Org. Chem., 62 (1997) 5755, and references cited therein.
14. (a) H.S. Nalwa, Appl. Organomet. Chem., 5 (1991) 349.
15. (b) T.J.J. Müller, M. Ansorge, H.J. Lindner, Chem. Ber.,129 (1996) 1433.
16. (c) U. Behreus, H. Brussard, H. Hagenau, J. Heck, E. Hendrickx, J. Körnich, J.G.M. van der Linden, A. Persoons, A.L. Speck, N. Veldman, Chem. Eur. J., 2 (1996) 98.
17. (d) E. Hendrickx, A. Persoons, S. Samson, G.R. Stephenson, J. Organomet. Chem., 542 (1997) 295.
18. (e) M. Bougault, K. Baum, H. Le Bozec, I. Ledoux; G. Pucetti, J. Zyss, New J. Chem., 22 (1998) 517.
19. (f) G. Roth, H. Fischer, T. Meyer-Friedrichsen, J. Heck, S. Houbrechts, A. Persoons, Organometallics, 17 (1998) 1511, and references cited therein.
20. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
21. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
22. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
23. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
24. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
25. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
26. For general reading on the synthesis and applications of Fischer-type carbene complexes: (a) K.H. Dötz, H. Fischer, P. Hoffmann, F.R. Kreissel, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, Verlag Chemie, Weinhein, Germany (1984). (b) L.S. Hegedus, Acc. Chem. Res., 28 (1995) 299. (c) D.B. Grotjahn, K.H. Dötz, Synlett., (1991) 381. (d) K.H. Dötz, in Organometallics in Organic Synthesis: Aspects of a Modern Interdisciplinary Field, A. de Meijere, H. tom Dieck (Eds), Springer, Berlin (1988). (e) W.D. Wulff, in Comprehensive Organic Synthesis, vol 5, pp 106, H.B. Trost, I. Fleming (Eds), Pergamon Press, New York (1991). (f) R. Aumann, K. Stein. M. Grehl, Synlett., (1993) 669. (g) A Parlier. M. Rudler, H. Rudler, R. Gaumont, J. Daran, J Vaissermann, Organometallics, 14 (1995) 2760.
27. Maiorana S., Papagni A., Licandro E., Persoons A, Clays K., Houbrechts S., Porzio W. Gazz. Chim. It. 125:1995;377.
28. Baldoli C., Hellier P., Licandro E., Maiorana S., Manzotti R., Papagni A. Tetrahedron. Lett. 38:1997;3769.
29. Burgess E.M., Penton H.R., Taylor E.A. J. Org. Chem. 38:1973;26.
30. Clays K., Persoons A. Phys. Rev. Lett. 66:1991;2980.
31. Hoffmann R. Angew. Chem. Int. Ed. Engl. 21:1982;711.
32. 5Cr=C group and a tertiary amide functionality clearly determines the NLO response of polyenes "push-pull" structures.
33. (a) B.A. Anderson, W.D. Wulff, T.S. Powers, S. Tribbit, A.L. Rheingold, J. Am. Chem. Soc., 114 (1992), 10785.
34. (b) E. Licandro, S. Maiorana, A. Papagni, A. Zanotti-Gerosa, F. Cariati, S. Bruni, M. Moret, A. Chiesi-Villa, Inorg. Chim. Acta, 220 (1994) 233.
35. (a) J.O. Morley, J. Chem. Soc. Perkin Trans. 2, (1995) 177.
36. (b) M.G. Hutchings, I. Ferguson, D.J. McGeein, J.O. Morley, J. Zyss, I. Ledoux, J. Chem. Soc. Perkin Trans. 2, (1995) 171.
37. (c) F. Effenberger, F. Würthner, Angew. Chem. Int. Ed. Engl., 32 (1993) 719.
38. (d) P.V. Bedworth, J. Cai, A Jen, S.R. Marder, J. Org. Chem., 61 (1996) 2242.
39. (e) L. Lancellotti, R. Tubino, S. Luzzati, E. Licandro, S. Maiorana, A. Papagni, Synth. Metals, 93 (1998) 27, and references cited therein.
40. (a) J. Nakayama, T. Fujimori, Heterocycles, 32 (1991) 991.
41. (b) A. Berlin, S. Bradamante, R. Ferraccioli, G. Pagani, F. Sannicolò, J. Chem. Soc. Perkin Trans. 1, (1987) 2631.
42. J.A. Connor, E.M. Jones, J. Chem. Soc. A, (1971) 1974.
43. C. Baldoli, P. Del Buttero, E. Licandro, S. Maiorana, A. Papagni, A. Zanotti-Gerosa, Synlett., (1993) 935.
44. Kiuki F., Nakamura N., Tsuda Y., Kondo K., Yoshimura M. Chem. Pharm. Bull. 36:1988;2452.