Synthesis and long wavelength hyper-Rayleigh scattering measurements of extended μ-vinylidene di-iron donor based organometallic merocyanines

Journal of Organometallic Chemistry

Volumn 625, Issue 1, 2001, Pages 32-39

  Farrell, Tony ^a,b   Meyer Friedrichsen, Timo ^b   Malessa, Maik ^b   Wittenburg, Christian ^b   Heck, Jürgen ^b   Manning, Anthony R ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Dicyanovinyl; Long wavelength hyper Rayleigh scattering (HRS); Merocyanine; Nonlinear optics (NLO); Organometallic; Solvatochromism

Indexed keywords

EID: 0002653218     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00779-8     Document Type: Article

References (60)

1. (a) H.S. Nalwa, S. Miyata, (Eds.) in: Nonlinear Optics of Organic Molecules and Polymers, CRC Press, New York, 1997.
2. (b) R.W. Boyd in: Nonlinear Optics, Academic Press, New York, 1992.
3. (c) P.N. Prasad, D.J. Williams, in: Nonlinear Optical Effects in Molecules & Polymers, Wiley, New York 1991.
4. (d) J.J. Wolff, R. Wortmann, Advances in Physical Organic Chemistry, (1999) 121.
5. (e) J.A. Delaire, K. Nakatani, Chem. Rev. 100 (2000) 1817.
6. (a) D.R. Kanis, M.A. Ratner, T.J. Marks, Chem. Rev. 94 (1994) 195.
7. (b) N.J. Long, Angew. Chem. 107 (1995) 37; Angew. Chem. Int. Ed. Engl. 34 (1995) 21.
8. (b) N.J. Long, Angew. Chem. 107 (1995) 37; Angew. Chem. Int. Ed. Engl. 34 (1995) 21.
9. (c) H.S. Nalwa, Appl. Organomet. Chem. 5 (1991) 349.
10. (d) I.R. Whittall, A.M. McDonagh, M.G. Humphrey, M. Samoc, Adv. Organomet. Chem. 42 (1998) 291.
11. (e) H. Wong, T. Meyer-Friedrichsen, T. Farrell, C. Mecker, J. Heck, Eur. J. Inorg. Chem. (2000) 631.
12. (f) J. Heck, S. Dabek, T. Meyer-Friedrichsen, H. Wong, Coord. Chem. Rev. 190 (1999) 1217.
13. (g) K.N. Jayaprakash, P.C. Ray, I. Matsuoka, M.M. Bhadbhade, V.G. Puranik, P.K. Das, H. Nishihara, A. Sarkar, Organometallics 18 (1999) 3851.
14. (h) O. Briel, K. Sünkel, I. Krossing, H. Nöth, E. Schmälzlin, K. Meerholz, C. Braüchle, W. Beck, Eur. J. Inorg. Chem. (1999) 483.
15. (i) J. Mata, S. Uriel, E. Peris, R. Liusar, S. Houbrechts, A. Persoons, J. Organomet. Chem. 562 (1998) 197.
16. (j) I.S. Lee, S.S. Lee, Y.K. Chung, D. Kim, N.W. Song, Inorg. Chim. Acta 279 (1998) 243.
17. Calabrese J.C., Cheng L.-T., Green M.L.H., Marder S.R. J. Am. Chem. Soc. 1134:1991;7227.
18. Wu Z., Ortiz R., Fort A., Barzoukas M., Marder S.R. J. Organomet. Chem. 528:1997;217.
19. (a) J.A. Bandy, H.E. Bunting, M.-H. Garcia, M.L.H. Green, S.R. Marder, M.E. Thompson, Polyhedron 12 (1992) 1429.
20. (b) T. Farrell, T. Meyer-Friedrichsen, J. Heck, A.R. Manning, Organometallics, 19 (2000) 3410.
21. Casey C.P., Konings M.S., Marder S.R. J. Organomet. Chem. 345:1988;125.
22. G.M. Dawkins, M. Green, J.C. Jeffrey, C. Sambale, F.G.A. Stone, J. Chem. Soc. Dalton Trans. (1983) 499.
23. 2 was prepared from the reaction of 4-bromobenzylchloride with triethyl phosphite.
24. 2Cl (which was obtained from the reaction of 2-bromothiophene with para formaldehyde in conc. HCl) with triethyl phosphite.
25. (a) C.P. Casey, M.S. Konings, R.E. Palermo, R.E. Colborn, J. Am. Chem. Soc. 107 (1985) 5296.
26. (b) C.P. Casey, M.S. Konings, S.R. Marder, Polyhedron 7 (1988) 881.
27. (c) M. Etienne, J. Talarmin, L. Toupet, Organometallics 11 (1992) 2058.
28. (d) C.P. Casey, S.R. Marder, Organometallics 4 (1985) 411.
29. Casey C.P., Konings M.S., Marder S.R., Takezawa Y. J. Organomet. Chem. 358:1988;347.
30. (a), S.R. Marder, J.W. Perry, Adv. Mater. 5 (1993) 804.
31. (b) J.L. Oudar, D.S. Chemla, Chem. Phys. 66 (1977) 2664.
32. (c) E. Hendrickx, K. Clays, A. Persoons, C. Dehu, J.L. Brédas, J. Am. Chem. Soc. 117 (1995) 3547.
33. (a) C. Dehu, F. Meyers, E. Hendrickx, K. Clays, A Persoons, S.R. Marder, J.L. Bredas, J. Am. Chem. Soc. 117 (1995) 10127.
34. (b) G. Bourhill, J.L. Bredas, L.T. Cheng, S.R. Marder, F. Meyers, J.W. Perry, B.G. Tiemann, J. Am. Chem. Soc. 116 (1994) 2619.
35. (c) G. Maas, B. Feith, Angew. Chem. 97 (1985) 518; Angew. Chem. Int. Ed. Engl. 24 511.
36. (c) G. Maas, B. Feith, Angew. Chem. 97 (1985) 518; Angew. Chem. Int. Ed. Engl. 24 511.
37. (d) B. Feith, H.-M. Weber, G. Maas, Chem. Ber. 119 (1986) 3276.
38. (e) H.-M. Weber, G. Maas, Chem. Ber. 121 (1988) 1791.
39. (f) C. Reichardt, in: Solvents and Solvent Effects in Organic Chemistry, second ed. VCH, Weinheim, 1988.
40. (a) L.G.S. Brooker, G.H. Keyes, D.W. Heseltine, J. Am. Chem. Soc. 73 (1951) 5350.
41. (b) K. Dimroth, C. Reichardt, T. Siepmann, F. Reichardt, Liebigs Ann. Chem. 661 (1963) 1.
42. (c) K. Dimroth, C. Reichardt, Liebigs Ann. Chem. 727 (1969) 93.
43. (d) S. Spange, E. Vilsmeier, S. Adolph, A. Fährmann, J. Phys. Org. Chem. 12 (1999) 547.
44. Clays K., Persoons A. Rev. Sci. Instrum. 63:1992;3285.
45. (a) K. Clays, E. Hendrickx, T. Verbiest, A. Persoons, Adv. Mater. 10 (1998) 643.
46. (b) J.J. Wolff, R. Wortmann, J. Prakt. Chem. 340 (1998) 99.
47. (c) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, J. Phys. Chem. 100 (1996) 6927.
48. (d) T. Farrell, T. Meyer-Friedrichsen M. Malessa, D. Haase, W. Saak, I. Asselberghs, K. Wostyn, K. clays, A. Persoons, J. Heck, A.R. Manning, J. Chem. Soc. Dalton Trans (2001), 20-36.
49. (a) K. Clays, E. Hendrickx, T. Verbiest, A. Persoons, Adv. Mater. 10 (1998) 643.
50. (b) J.J. Wolff, R. Wortmann, J. Prakt. Chem. 340 (1998) 99.
51. Stadler S., Dietrich R., Bourhill G., Bräuchle C., Pawlik A., Grahn W. Chem. Phys. Lett. 247:1995;271.
52. Kodaira T., Watanabe A., Ito O., Matsuda M., Clays K., Persoons A. J. Chem. Soc. Faraday Trans. 93:1997;3039.
53. Lambert C., Nöll G., Schmälzlin E., Merholz K., Bräuchle C. Chem. Eur. J. 4:1998;2129.
54. Clays K., Persoons A., De Maeyer L. Adv. Chem. Phys. 85:1994;455.
55. Lambert C., Gaschler W., Schmälzlin E., Merholz K., Bräuchle C. J. Chem. Soc. Perkin Trans. 2:1999;577.
56. (a) S.R. Marder, C.B. Gorman, F. Meyers, J.W. Perry, G. Bourhill, J.L. Bredas, B.M. Pierce, Science 265 (1994) 632.
57. (b) K. Clays, E. Hendrickx, M. Triest, T. Verbiest, A. Persoons, C. Dehu, J.L. Bredas, Science 262 (1993) 1419.
58. (c) D. Lu, G. Chen, J.W. Perry, W.A. Goddard III, J. Am. Chem. Soc. 116 (1994) 10679.
59. (d) F. Meyers, S.R. Marder, B.M. Pierce, J.L. Bredas, J. Am. Chem. Soc. 116 (1994) 10703.
60. Paralite Optical Parametrical Oscillator, LAS GmbH.