An organosilicon dendrimer composed of 16 thiophene rings

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6043-6046

  Nakayama, Juzo ^a   Lin, Jin Song ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030790619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01356-7     Document Type: Article

References (27)

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2. (b) H. Uchida, Y. Kabe, K. Yoshino, A. Kawamata, T. Tsumuraya, and S. Masamune, J. Am. Chem. Soc., 1990, 112, 7077;
3. (c) L. J. Mathias and T. W. Carothers, J. Am. Chem. Soc., 1991, 113, 4043;
4. (d) A. Morikawa, M. Kakimoto, and Y. Imai, Macromolecules, 1991, 24, 3469.
5. Carbosilane dendrimers. (a) A. W. van der Made and P. W. N. M. van Leeuwen, J. Chem. Soc., Chem. Commun., 1992, 1400;
6. (b) L.-L. Zhou and J. Roovers, Macromolecules, 1993, 26, 963;
7. (c) J. Roovers, L.-L. Zhou, P. M. Toporowski, M. van der Zwan, H. latrou, and N. Hadjichristidis, Macromolecules, 1993, 26, 4324;
8. (d) D. Seyferth, D. Y. Son, A. L. Rheingold, and R. L. Ostrander, Organometallics, 1994,13, 2682;
9. (e) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leuuwen, P. Wijkens, D. M. Grove, and G. van Koten, Nature, 1994, 372, 659.
10. Polysilane dendrimers. (a) J. B. Lambert, J. L. Pflug, and C. L. Stern, Angew. Chem., Int. Ed. Engl., 1995, 34, 98;
11. (b) H. Suzuki, Y. Kimata, S. Sato and A. Kuriyama, Chem. Lett., 1995, 293;
12. (c) A. Sekiguchi, M. Nanjo, C. Kabuto, and H. Sakurai, J. Am. Chem. Soc., 1995,117, 4195.
13. Only representative examples are given below. a-Thiophene oligomers: (a) J. Nakayama, T. Konishi, and M. Hoshino, Heterocycles, 1990, 27, 1731;
14. (b) W. ten Hoeve, H. Wynberg, E. E. Havinga, and E. W. Meijer, J. Am. Chem. Soc., 1991, 113, 5887 and references cited therein. Thiophene-pyrrole cooligomers:
15. (c) B. A. Merrill and E. LeGoff, J. Org. Chem., 1990, 55, 2904;
16. (d) M. R. Johnson, D. C. Miller, K. Bush, J. J. Becker, and J. A. Ibers, J. Org. Chem., 1992, 57, 4414.
17. Thiophene-derived macrocycles: (e) Z. Hu and M. P. Cava, Tetrahedron Lett., 1994, 35, 3493.
18. Orthogonally-fused thiophene oligomers: (f) J. Nakayama and T. Fujimori, J. Chem. Soc., Chem. Commun., 1991, 1614;
19. (g) J. Guay, A. Diaz, R. Wu, and J. M. Tour, J. Am. Chem. Soc., 1993, 115, 1869 and references cited therein. Cofacially-oriented thiophene oligomers:
20. (h) K. Kuroda, J. Nakayama, M. Hoshino, N. Furusho, and S. Ohba, Tetrahedron Lett., 1994, 35, 3957 and references cited therein. Thiophene-silole cooligomers:
21. (i) K. Tamao, S. Yamaguchi, M. Shiozaki, Y. Nakagawa, and Y. Ito, J. Am. Chem. Soc., 1992, 114, 5867.
22. E. Lukevics, O. A. Pudova, J. Popelis, and N. P. Erchak, Zh. Obsch. Khim., 1981, 51, 115.
23. For electropolymerization of 1: A. Guy, M. Lemaire, R. Garreau, and H. A. Hoa, J. Electroanal. Chem., 1991, 312, 277. For ruthenium complexes of 1: M.-H. Woo and M.-G. Choi, 4th International Conference on Heteroatom Chemistry, Seoul, Korea, Abst. No. PA-40.
24. For electropolymerization of 1: A. Guy, M. Lemaire, R. Garreau, and H. A. Hoa, J. Electroanal. Chem., 1991, 312, 277. For ruthenium complexes of 1: M.-H. Woo and M.-G. Choi, 4th International Conference on Heteroatom Chemistry, Seoul, Korea, Abst. No. PA-40.
25. max (E) 327.5 nm (88900).
26. 2/hexane (1/3) to give 55 mg (10%) of 1, 92 mg (10%) of 2, 309 mg (22%) of 4, 500 mg (28%) of 5, and 446 mg (19%) of 6 (separation of 4-6 by column chromatography is incomplete; these were separated by HPLC on a column of JAIGEL-2H (Japan Analytical Industry Co.) to give them in the yields given above).
27. For tetrakis(2,2′:5′,2″-terthiophene-2-yl)silane, see J. Roncali, C. Thobie-Gautier, H. Brisset, J.-F. Favart, and A. Guy, J. Electroanal. Chem., 1995, 381, 257.