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Synthesis and Characterization of Poly(p-phenylene ethynylene)s with nitroxyl radical endgroups

Published online by Cambridge University Press:  27 February 2012

Michael Schroeter ,
M. Behl ,
C. Weder  and
A. Lendlein
Michael Schroeter
Affiliation:
Centre for Biomaterial Development, Institute of Polymer Research, Helmholtz-Centre Geesthacht, Kantstr. 55, 14513 Teltow, Germany.
M. Behl
Affiliation:
Centre for Biomaterial Development, Institute of Polymer Research, Helmholtz-Centre Geesthacht, Kantstr. 55, 14513 Teltow, Germany.
C. Weder
Affiliation:
Adolphe Merkle Institute for Polymer Chemistry and Materials, University of Fribourg, CH-1723 Marly 1, Switzerland.
A. Lendlein
Affiliation:
Centre for Biomaterial Development, Institute of Polymer Research, Helmholtz-Centre Geesthacht, Kantstr. 55, 14513 Teltow, Germany.
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Abstract

The generation of terminal N-Hydroxyl substituents in p-phenylene ethynylene based compounds is presented. P-phenylene ethynylene derivatives were synthesized in a Sonogashira coupling reaction. N-Hydroxyl groups could be introduced by lithiation of iodine moieties and subsequent reaction with the 2-methyl-2-nitrosopropane generated by the cleavage of its dimer. The synthesis by lithiation was found to be more effective compared to the reaction with the Grignard reagent and the chloro-derivative. The resulting compounds were characterized by 1H NMR, UV and PL spectroscopy and were shown to be sensitive towards oxidation. This new approach of introducing additional charge carriers by nitroxyl endgroups might enable conjugated polymers with enhanced conductivity.

Keywords

chemical synthesisnuclear magnetic resonance (NMR)optical properties
Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 1403: Symposium V – Multifunctional Polymer-Based Materials , 2012 , mrsf11-1403-v18-03
Copyright
Copyright © Materials Research Society 2012

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References

REFERENCES

1. Shirakawa, H., et al. ., J. Chem. Soc. Chem. Comm., 578 (1977).Google Scholar
2. Heeger, A.J., J. Phys. Chem., 105, 8475 (2001).Google Scholar
3. Skotheim, T.J., Elsenbaumer, R.L., and Reynolds, J.R., in Handbook of Conducting Polymers, 2nd Edition (Dekker, New York, 1998).Google Scholar
4. Greiner, A. and Weder, C., in Encyclopedia of Polymer Science and Technology, edited by Kroschwitz, J.I. (Wiley-Interscience, New York, 2001).Google Scholar
5. Mc Quade, D.T., Pullen, A.E., and Swager, T.M., Chem. Rev., 100, 2537 (2000).Google Scholar
6. Horowitz, G., Adv. Mater., 10, 365 (1998).Google Scholar
7. Brabec, C.J., Sariciftci, N.S., and Hummelen, J.C., Adv. Funct. Mater., 11, 15 (2001).Google Scholar
8. Weder, C., in Poly(arylene ethynylene)s – From Synthesis to Application (Springer, Berlin Heidelberg, 2005).Google Scholar
9. van Meurs, P.J. and Janssen, R.A., J. Org. Chem., 65, 5712 (2000).Google Scholar
10. van Meurs, P.J. and Janssen, R.A., Synth. Met., 121, 1832 (2001).Google Scholar
11. Dixon, D.D. and Burgoyne, W.F., Appl. Catal., 62, 161 (1990).Google Scholar
12. Forrester, A.R. and Hepburn, S.P., J. Chem. Soc (C), 701 (1971).Google Scholar
13. Burnworth, M., et al. ., Macromolecules, 41, 2157 (2008).Google Scholar
14. Weder Ch, W.M.., Macromolecules, 29, 5157 (1996).Google Scholar