Hostname: page-component-8448b6f56d-42gr6 Total loading time: 0 Render date: 2024-04-24T10:21:53.734Z Has data issue: false hasContentIssue false

Synthesis and Physical Properties of Self-Orienting Head-To-Tail Polythiophenes.

Published online by Cambridge University Press:  16 February 2011

Richard D. McCullough
Affiliation:
Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213.
Shawn P. Williams
Affiliation:
Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213.
Manikandan Jayaraman
Affiliation:
Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213.
Jerry Reddinger
Affiliation:
Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213.
Lynnette Miller
Affiliation:
Department of Chemistry, Carnegie Mellon University, Pittsburgh, PA 15213.
Stephanie Tristram-Nagle
Affiliation:
Department of Biological Sciences, Carnegie Mellon University, Pittsburgh, PA 15213
Get access

Abstract

Designed synthesis and architectural assembly of head-to-tail polythiophene derivatives provide the ability to control π orbital topology and orbital interactions in conjugated polymers. The preparation of polythiophene derivatives with essentially 100% head-to tail (HT) couplings leads to defect free polythiophenes. These new HT polythiophenes can undergo macromolecular self-assembly to give self-oriented conducting polymers. Study of these materials has led to new insights on structure-property relationships in this class of Materials. In addition, these results show that the molecular orbital overlap, the band dimensionality, and the solid state structure are quite sensitive to the nature of the side chains attached to the polymer's backbone. In addition, we have now synthesized the first heteroatom functionalized HT polythiophenes. These polythiophene derivatives can bind cations, and ion recognition can be used to tune conjugation lengths and properties in polythiophenes. Also presented are a class of random HT coupled 3-alkylthiophenes whose optical and electrochemical properties and possibly electronic properties can be altered by recipe.

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. McCullough, R. D., Lowe, R. D., J. Chem. Soc., Chem. Commun. 70, (1992).Google Scholar
2. McCullough, R. D., Lowe, R. D., Jayaraman, M., Anderson, D. L., J. Org. Chem. 58, 904, (1993). All of the 1H and 13C NMR spectra of our HT-poly (3-alkylthiophenes) and other proof of couplings has been previously published in the above reference.Google Scholar
3. McCullough, R. D., Tristram-Nagle, S., Williams, S. P., Lowe, R. D., Jayaraman, M., J. Am Chem. Soc. 115, 4910, (1993).Google Scholar
4. McCullough, R. D., Williams, S. P., J. Am. Chem. Soc. (1993), in press.Google Scholar
5. McCullough, R. D., Jayaraman, M., Manuscript in preparation.Google Scholar
6. Roncali, J., Chem. Rev. 92, 711 (1992).Google Scholar
7. Chen, T.-A., Rieke, R. D., J. Am. Chem. Soc. 114, 10087, (1992).CrossRefGoogle Scholar
8. Souto Maior, R. M., Hinkelmann, K., Eckert, H., Wudl, F., Macromolecules 23, 1268, (1990).Google Scholar
9. Sato, M., Morii, H., Macromolecules 24, 1196, (1991).Google Scholar
10. Prosa, T. J., Winokur, M. J., Moulton, J., Smith, P., Heeger, A. J., Macromolecules 25, 4364 (1992).CrossRefGoogle Scholar
11. Mardalen, J., Samuelsen, E., Gautun, O. R., Carlsen, P. H., Solid State Commun. 80, 687, (1991).Google Scholar
12. Chen, S.-A., Ni, J.-M., Macromolecules 25, 6081, (1992).CrossRefGoogle Scholar
13. Patii, A. O., Heeger, A. J., Wudl, F., Chem. Rev. 88, 183, (1988).Google Scholar
14. Bryce, M. R., Chissel, A., Kathirgamanathan, P., Parker, D., Smith, N. M., J. Chem. Soc., Chem. Commun. 679, (1987).Google Scholar
15. Pei, Q., Inganas, O., et al. Synth. Met. 55, 1221, (1993).Google Scholar
16. Inganas, O., Salaneck, W. R., Osterholm, J.-E., Laakso, J., Synth. Met. 22, 395, (1988).Google Scholar