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Synthesis of A 1,1′-Binaphthyl Based Main Chain Chiral Conjugated Polymer

Published online by Cambridge University Press:  10 February 2011

Qiao-Sheng Hu
Affiliation:
Department of Chemistry, North Dakota State University, Fargo, ND 58105
Dilrukshi Vitharana
Affiliation:
Department of Chemistry, North Dakota State University, Fargo, ND 58105
Lin Pu
Affiliation:
Department of Chemistry, North Dakota State University, Fargo, ND 58105
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Abstract

The synthesis and characterization of a 1,1′-binaphthyl based main chain chiral conjugated polymer, R-9, is described. The polymer is prepared from the palladium-catalyzed Suzuki coupling of an optically active binaphthyl molecule, (R)-2,2′-dihexyloxy-1,1′-binaphthyl-6,6′- diboronic acid, R-4 with 1,4-bis(p-bromostyryl)benzene (E:Z = 1:1.2), 8. The Suzuki coupling of 8 with 6-neopentyloxynaphthyl-2-boronic acid, 1 1, leads to the formation of a conjugated molecule 10. The structure of this molecule represents the repeat unit of R-9. The electronic absorption spectrum of 10 demonstrates that the degree of conjugation in the chiral conjugated polymer is almost the same as that of its repeat unit.

Type
Research Article
Copyright
Copyright © Materials Research Society 1996

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References

REFERENCES

1. (a) Skotheim, T.A., Handbook of Conducting Polymers. Vol.1 and 2 (Marcel Dekker: New York, 1986). (b) J.L. Bredas and R. Silbey, Conjugated Polymers: the Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials (Kluwer Academic Publishers: Boston, 1991). (c) H.G. Kiess, Conjugated Conducting Polymers (Springer-Verlag: New York, 1992).Google Scholar
2. Marder, S.R., Sohn, J.E. and Stucky, G.D., Materials for Nonlinear Optics. Chemical Perspectives (ACS Symposium Series No. 455; American Chemical Society: Washington, DC 1991).Google Scholar
3. (a) Moore, J.S., Gorman, C.B. and Grubbs, R.H., J. Am. Chem. Soc. 113, 1704, (1991). (b) D. Kotkar, V. Joshi and P. Ghosh, J. Chem. Soc., Chem. Commun. 917 (1988). (c) M. Lemaire, D. Delabouglise, R. Garreau, A. Guy and J. Roncali, J. Chem. Soc., Chem. Commun. 658 (1988).Google Scholar
4. Komori, T., Nonaka, T., J. Am. Chem. Soc. 106, 2656 (1984).Google Scholar
5. (a) Rosini, C., Franzini, L., Raffaelli, A., Salvadori, P., Synthesis 503 (1992). (b) J.K. Whitesell, Chem. Rev. 89, 1581 (1989). (c) G. Bringmann, R. Walter and R. Weirich, Angew. Chem. Int. Ed. Engl. 29, 977 (1990).Google Scholar
6. A communication on this polymer including its synthesis, conductivity measurement, thermal analysis, circular dichroism spectrum and atomic force microscopic study has been accepted by Macromolecules.Google Scholar
7. Hu, Q.-S., Vitharana, D. and Pu, L., Tetrahedron: Asymmetry, 6, 2123 (1995).Google Scholar
8. (a) Kyba, E.P., Gokel, G.W., de Jong, F., Koga, K., Sousa, L.R., Siegel, M.G., Kaplan, L., Sogah, G.D.Y. and Cram, D.J., J. Org. Chem. 42, 4173 (1977). (b) W. Pradellok, A. Kotas, W. Walczyk and Z. Jedlinski, Chem. Abstr. 90, 121289t (1979).Google Scholar
9. Coutts, I.G.C., Goldschmid, H.R. and Musgrave, O.C., J. Chem. Soc. (C). 488 (1970)Google Scholar
10. McDonald, R.N. and Campbell, T.W., J. Am. Chem. Soc. 82, 4669 (1960).Google Scholar
11. (a) Miyaura, N., Yanagi, T., Suzuki, A., Synth. Comm. 11, 513 (1981). (b) T.I. Wallow and B.M. Novak, J. Am. Chem. Soc. 113, 7411 (1991). (c) J. Huber, U. Scherf, Macromol. Rapid Commun. 15, 897 (1994).Google Scholar