Synthesis and properties of silole-containing σ- and π-conjugated compounds

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 56, Issue 6, 1998, Pages 500-510

  Yamaguchi, Shigehiro ^a   Tamao, Kohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Intramolecular reductive cyclization; Oligosilole; Organic electroluminescent device; Polysilole; Silacyclopentadiene; Silole; Conjugated polymer; * * Conjugation

Indexed keywords

EID: 0242384977     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.56.500     Document Type: Article

References (71)

1. (a) J. Dubac, A. Laporterie, G. Manuel, Chem. Rev., 90, 215 (1990);
2. (b) E. Colomer, R. J.P. Corriu, M. Lheureux, Chem. Rev., ibid., 90, 265 (1990);
3. (c) J. Dubac, C. Guerin, P. Meunier, "The Chemistry of Organic Silicon Compounds", ed. by Z. Rappoport, Y. Apeloig, Vol.2, John Wiley & Sons, 1998, in press.
4. W.P. Freeman, T.D. Tilley, L.M. Liable-Sands, A.L. Rheingold, J. Am. Chem. Soc., 118, 10457 (1996) and references cited therein.
5. W.P. Freeman, T.D. Tilley, A.L. Rheingold, J. Am. Chem. Soc., 116, 8428 (1994)
6. (a) K. Tamao, S. Yamaguchi, Pure Appl. Chem., 68, 139 (1996);
7. (a) E.G. Janzen, J.B. Pickett, W.H. Atwell, J. Organomet. Chem., 10, P6 (1967);
8. (b) D.H. O'Brien, D.L. Breeden, J. Am. Chem. Soc., 103, 3237 (1981)
9. S. Yamaguchi, K. Tamao, Bull. Chem. Soc. Jpn., 69, 2327 (1996)
10. (a) V. Niessen, W.P. Kraemer, L.S. Cederbaum, Chem. Phys., 11, 385 (1975);
11. (b) M.S. Gordon, P. Boudjouk, F. Anwari, J. Am. Chem. Soc., 105, 4972 (1983);
12. (c) C. Guimon, G. Pfister-Guillouzo, J. Dubac, A. Laporterie, G. Manuel, H. Iloughmane, Organometallics, 4, 636 (1985);
13. (d) V.N. Khabashesku, S.E. Balaji, V. Boganov, O.M. Nefedov, J. Michl, J. Am. Chem. Soc., 116, 320 (1994);
14. (e) B. Goldfuss, P.V.R. Schleyer, Organometallics, 14, 1553 (1995)
15. K. Tamao, S. Ohno, S. Yamaguchi, Chem. Commun., 1996, 1873
16. K. Tamao, S. Yamaguchi, Y. Ito, Y. Matsuzaki, T. Yamabe, M. Fukushima, S. Mori, Macromolecules, 28, 8668 (1995)
17. (a) B. Wrackmeyer, J. Chem. Soc., Chem. Commun., 1986, 397;
18. (b) B. Wrackmeyer, idem, J. Organomet. Chem., 310, 151 (1986);
19. (c) R. Köster, G. Seidel, J. Süß, B. Wrackmeyer, Chem. Ber., 126, 1107 (1993);
20. (d) B. Wrackmeyer, G. Kehr, J. Süß, Chem. Ber., ibid., 126, 2221 (1993)
21. K. Tamao, S. Yamaguchi, M. Shiro, J. Am. Chem. Soc., 116, 11715 (1994)
22. A recent review on acetylene oligomerization: R. Gleiter, D. Kratz, Angew. Chem., Int. Ed. Engl., 32, 842 (1993)
23. For example (a) N.E. Schore, In Comprehensive Organic Synthesis, B.M. Trost, I. Fleming Eds., Pergamon Press, Oxford, UK, Vol.5, 1991, p.1129;
24. (b) E. Negishi, In Comprehensive Organic Synthesis, B.M. Trost, I. Fleming Eds., Pergamon Press, Oxford, UK, Vol.5, 1991, p.1163
25. (a) H.W. Gibson, F.C. Bailey, A.J. Epstein, H. Rommelmann, S. Kaplan, J. Harbour, X.-Q. Yang, D.B. Tanner, J. M. Pochan, J. Am. Chem. Soc., 105, 4417 (1983);
26. (b) T. Kusumoto, T. Hiyama. Chem. Lett., 1988, 1149;
27. (c) T. J. Barton, S. Ijadi-Maghsoodi, Y. Pang, Macromolecules, 24, 1257 (1991)
28. (a) R.G. Bergman, Acc. Chem. Res., 6, 25 (1973);
29. (b) K.N. Bharncha, R.M. Marsh, R. E. Minto, R.G. Bergman, J. Am. Chem. Soc., 115, 3120 (1993)
30. L.I. Smith, H.H. Hoehn, J. Am. Chem. Soc., 63, 1184 (1941)
31. S. Yamaguchi, K. Tamao, Tetrahedron Lett., 37, 2983 (1996)
32. S. Grigoras, G.C. Lie, T.J. Barton, S. Ijadi-Maghsoodi, Y. Pang, J. Shinar, Z.V. Vardeny, K.S. Wong, S. G. Han, Synth. Met., 49-50, 293 (1992)
33. (a) G. Frapper, M. Kertész, Organometallics, 11, 3178 (1992);
34. (b) G. Frapper, M. Kertész, idem, Synth. Met., 55-57, 4255 (1993);
35. (c) J. Kürti, P.R. Surján, M. Kertesz, G. Frapper, Synth. Met., ibid., 55-57, 4338 (1993)
36. (a) Y. Yamaguchi, J. Shioya, Mol. Eng., 2, 339 (1993);
37. (b) Y. Yamaguchi, Mol. Eng., ibid., 3, 311 (1994);
38. (c) Y. Yamaguchi, T. Yamabe, Int. J. Quantum Chem., 57, 73 (1996)
39. (a) S.Y. Hong, D.S. Marynick, Macromolecules, 28, 4991 (1995);
40. (b) S.Y. Hong, S.J. Kwon, S.C. Kim, J. Chem. Phys., 103, 1871 (1995);
41. (c) S.Y. Hong, Bull. Korean. Chem. Soc., 16, 845 (1995);
42. (d) S.Y. Hong, S.J. Kwon, S.C. Kim, D.S. Marynick, Synth. Met., 69, 701 (1995);
43. (e) S.Y. Hong, S.J. Kwon, S.C. Kim, J. Chem. Phys., 104, 1140 (1996)
44. B.H. Lipshutz, K. Siegmann, E. Garcia, F. Kayser, J. Am. Chem. Soc., 115, 9276 (1993)
45. Y. Yamaguchi, Synth. Met., 82, 149 (1996)
46. S. Yamaguchi, R.-Z. Jin, K. Tamao, M. Shiro, Organometallics, 16, 2230 (1997)
47. S. Yamaguchi, R.-Z. Jin, K. Tamao, M. Shiro, Organometallics, 16, 2486 (1997)
48. K. Kanno, M. Ichinohe, C. Kabuto, M. Kira, Chem. Lett., 1998, 99
49. B.P.S. Chauhan, T. Shimizu, M. Tanaka, Chem. Lett., 1997, 785
50. T. Sakai, T. Sanji, H. Sakurai, 72nd Annual Meeting of the Chemical Society of Japan, Tokyo, March 1997, Abstract 3E307
51. (a) Z.-H. Zhou, T. Maruyama, T. Kanbara, T. Ikeda, K. Ichimura, T. Yamamoto, K. Tokuda, J. Chem. Soc., Chem. Commun., 1991, 1210;
52. (b) E.E. Havinga, W. ten Hoeve, H. Wynberg, Synth. Met., 55-57, 299 (1993);
53. (c) K. Tamao, S. Yamaguchi, Y. Ito, J. Chem. Soc., Chem. Commun., 1994, 229
54. K. Tamao, S. Yamaguchi, M. Shiozaki, Y. Nakagawa, Y. Ito, J. Am. Chem. Soc., 114, 5867 (1992)
55. J.W. Sease, L. Zechmeister, J. Am. Chem. Soc., 69, 270 (1947)
56. R.D. McCullough, R.D. Lowe, M. Jayaraman, D.L. Anderson, J. Org. Chem., 58, 904 (1993)
57. T. Kauffmann, L. Hexy, Chem. Ber., 114, 3674 (1981)
58. (a) T. Yamamoto, W. Yamada, M. Takagi, K. Kizu, T. Maruyama, N. Ooba, S. Tomaru, T. Kurihara, T. Kaino, K. Kubota, Macromolecules, 27, 6620 (1994);
59. (b) M. Moroni, J.L. Moigne, S. Luzzati, Macromolecules, ibid., 27, 562 (1994);
60. (c) M. Moroni, J.L. Moigne, T.A. Pham, J.-Y. Bigot, Macromolecules, ibid., 30, 1964 (1997)
61. S. Yamaguchi, K. Iimura, K. Tamao, Chem. Lett., 1998, 89
62. W. Chen, S. Ijadi-Maghsoodi, T.J. Barton, Polym. Prepr., 38, 189 (1997)
63. K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, S. Yamaguchi, J. Am. Chem. Soc., 118, 11974 (1996)
64. S. Yamaguchi, Y. Itami, K. Tamao, 72nd Annual Meeting of the Chemical Society of Japan, Tokyo, March 1997, Abstract 2E330
65. H. Okinoshima, K. Yamamoto, M. Kumada, J. Am. Chem. Soc., 94, 9263 (1972)
66. P.J. Fagan, W.A. Nugent, J.C. Calabrese, J. Am. Chem. Soc., 116, 1880 (1994)
67. S. Yamaguchi, R.-Z. Jin, K Tamao, M. Shiro, J. Organomet. Chem., in press.
68. S. Yamaguchi, T. Endo, K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, 74th Annual Meeting of the Chemical Society of Japan, Kyoto, March 1997, Abstract 4A211