Hostname: page-component-78c5997874-j824f Total loading time: 0 Render date: 2024-11-09T06:07:40.076Z Has data issue: false hasContentIssue false

A New Dithiophene Fused p-Phenylene Vinylene Conducting Polymer. Synthesis and Study

Published online by Cambridge University Press:  16 February 2011

Martin Pomerantz
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Jiping Wang
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Seeyearl Seong
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Kyle P. Starkey
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Long Nguyen
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Dennis S. Marynick
Affiliation:
Center for Advanced Polymer Research, Department of Chemistry and Biochemistry, Box 19065, The University of Texas at Arlington, Arlington, TX 76019–0065
Get access

Abstract

A new conducting polymer, poly (benzo[1,2-b:4,5-b′]dithiophene-4,8-diyl vinylene) (1), has been prepared by pyrolysis of a precursor polymer 2, which, in turn, was prepared by a multistep synthetic sequence (Scheme 1). The polymer has a UV-vis spectral maximum at 501 nm (2.48 eV), band-gap (band edge) of 1.92 eV and with FeC?3 doping a conductivity of 15 S cm1. Quantum Mechanical calculations using PRDDO, ab-initio and modified extended Hiickel Methodology on the Monomers, trimers and polymers, both aromatic and quinoid, provided structures and an absorption maximum band-gap which is consistent with either a planar aromatic polymer or a polymer which has both aromatic and quinoid units.

Type
Research Article
Copyright
Copyright © Materials Research Society 1994

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1. Pomerantz, M., Chaloner-Gill, B., Harding, L.O., Tseng, J.J., and Pomerantz, W.J., Synth. Met. 55, 960 (1993).CrossRefGoogle Scholar
2. Pomerantz, M., Chaloner-Gill, B., Harding, L.O., Tseng, J.J., and Pomerantz, W.J., J. Chem. Soc., Chem. Commun., 1672 (1992).CrossRefGoogle Scholar
3. Pomerantz, M., Tseng, J.J., Zhu, H., Sproull, S.J., Reynolds, J.R., Uitz, R., Arnott, H.J., and Haider, M.I., Synth. Met. 41, 825 (1991).Google Scholar
4. Williams, J.M., Ferraro, J.R., Thorn, R.J., Carlson, K.D., Geiser, U., Wang, H.H., Kini, A.M., and Whangbo, M.-H., Organic Superconductors (including Fullerenes) : Synthesis. Structure. Properties, and Theory. (Prentice Hall, Englewood Cliffs, NJ, 1992).Google Scholar
5. Williams, J.M., Ferraro, J.R., Thorn, R.J., Carlson, K.D., Geiser, U., Wang, H.H., Kini, A.M., and Whangbo, M.-H., Organic Superconductors (including Fullerenes): Synthesis. Structure. Properties, and Theory. (Prentice Hall, Englewood Cliffs, NJ, 1992), chapter 3.Google Scholar
6. van der Pauw, L.J., Phillips Tech. Rev. 20, 220 (19581959).Google Scholar
7. Elsenbaumer, R.L., and Shacklette, L.W., in Handbook of Conducting Polymers, edited by Skotheim, T. A. (Marcel Dekker, New York, 1986), vol. 1, chapter 6.Google Scholar
8. Parham, W.E., Wynberg, H., and Ramp, F.L., J. Am. Chem. Soc. 75, 2065 (1953).CrossRefGoogle Scholar
9. Wessling, R.A. and Zimmerman, R.G., U.S. Patent No. 3 401 152 (1968).Google Scholar
10. Capistran, J.D., Gagnon, D.R., Antoun, S., Lenz, R.W., and Karasz, F.E., Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 25, 282 (1984).Google Scholar
11. Murase, I., Ohnishi, T., Noguchi, T., and Hirooka, M., Polym. Commun. 25, 327 (1984).Google Scholar
12. Gagnon, D.R., Capistran, J.D., Karasz, F.E., Lenz, R.W., and Antoun, S., Polymer 25, 567 (1987).Google Scholar
13. Lenz, R.W., Han, C.-C., Stenger-Smith, J., and Karasz, F.E., J. Polym. Sci., Polym. Chem. Ed. 26, 3241 (1988).Google Scholar
14. Lin-Vien, D., Colthup, N.B., Fateley, W.G., and Grasselli, J.G., The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules. (Academic Press, San Diego, 1991), chapters 4 and 6.Google Scholar
15. Brown, A.R., Bradley, D.D.C., Burroughes, J.H., Friend, R.H., Greenham, N.C., Burn, P.L., Holmes, A.B., and Kraft, A., Appl. Phys. Lett. 61, 2793 (1992).CrossRefGoogle Scholar
16. Jen, K.-Y., Eckhardt, H., Jow, T.R., Shacklette, L.W., and Elsenbaumer, R.L., J. Chem. Soc, Chem. Commun., 1988. 215.CrossRefGoogle Scholar
17. Eckhardt, H., Shacklette, L.W., Jen, K.Y., and Elsenbaumer, R.L., J. Chem. Phys. 91, 1303 (1989).Google Scholar
18. Gregorius, R.M. and Karasz, F.E., Synth. Met. 53, 11 (1992).CrossRefGoogle Scholar
19. Murase, I., Ohnishi, T., Noguchi, T., and Hirooka, M., Synth. Met. 17, 639 (1987).Google Scholar
20. Jen, K.-Y., Shacklette, L.W., and Elsenbaumer, R., Synth. Met. 22, 179 (1987).Google Scholar
21. Halgren, T.A. and Lipscomb, W.N., J. Chem. Phys. 58, 1569 (1973).CrossRefGoogle Scholar
22. Marynick, D.S. and Lipscomb, W.N., Proc. Nat. Acad. Sci. U. S. A. 79, 1341 (1982).CrossRefGoogle Scholar
23. Marynick, D.S., Axe, F.U., Kirkpatrick, C.M., and Throckmorton, L., Chem. Phys. Lett. 99, 406 (1982).CrossRefGoogle Scholar
24. Marynick, D.S. and Reid, R.D., Chem. Phys. Lett. 124, 17 (1986).CrossRefGoogle Scholar
25. Gaussian 92, Revision C, Frisch, M.J., Head-Gordon, H.B., Schlegel, H.B., Raghavachari, K., Binkley, J.S., Gonzalez, C., Defrees, D.J., Fox, D.J., Whiteside, R.A., Seeger, R., Melius, C.F., Baker, J., Martin, R.L., Kahn, L.R., Stewart, J.J.P., Fluder, E.M., Topiol, S., and Pople, J.A., Gaussian Inc., Pittsburgh, PA, 1992.Google Scholar
26. Hoffmann, R., J. Chem. Phys. 39, (1963).Google Scholar
27. Whangbo, M.H. and Hoffmann, R., J. Am. Chem. Soc. 100, 6093 (1978).CrossRefGoogle Scholar
28. Whangbo, M.H., Hoffmann, R., and Woodward, R.B., Proc. Roy. Soc. (London) A 366, 23 (1979).Google Scholar
29. Hong, S.Y. and Marynick, D.S., J. Chem. Phys. 96, 5497 (1992).CrossRefGoogle Scholar