Abstract
Processibility of conjugated and conducting polymers is one of the major topics in the chemistry and applications of these polymers. In this paper we describe the gasphase photopolymerization of phenyl azides, that yield thin films of poly-1,2-azepines on a variety of substrates. The photochemistry occurs at the interface of substrate and gas-phase and the polymer is grown at the surface of the substrate. High resolution patterns of poly-1,2-azepines are formed when a photomask is used in this gasphase photopolymerization. Upon oxidative doping with iodine or arsenic pentafluoride these polymers exhibit conductivities up to 0.01 S/cm. Mechanism, kinetics and versatility of the photopolymerization of phenyl azide and a series of substituted phenyl azides is discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Shirakawa, H.; Louis, E.J.; MacDiarmid, A.G.; Chiang, C.K.; Heeger, A.J. J. Chem. Soc, Chem. Commun. 1977, 578; Chiang, C.K.; Fincher, C.R.; Park, Y.W.; Heeger, A.J.; Shirakawa, H.; Louis, E.J.; Gau, S.C; MacDiarmid, A.G. Phys. Rev. Lett. 1977 39, 1098; Diaz, A.F.; Kanazawa, K.K.; Gardini, G.P. J. Chem. Soc, Chem. Commun., 1979, 653.
Handbook Conducting Polymers Skotheim, T.A. Ed., Marcel Dekker, New York, 1986, Vol 1 and 2.
Edwards, J.H.; Feast, W.J. Polymer, 1980 21, 595
Feast W.J. in Handbook Conducting Polymers Skotheim, T.A. Ed., Marcel Dekker, New York, 1986, p1.
Kanbe, M.; Okawara, M. J. Pol. Sci. A1, 1968, 6, 1058
Gagnon, D.R.; Capistron, J.O.; Karasz, F.E.; Lenz, R.W. Polym. Bull. 1984, 12, 293.
Sato, M.; Tanaka, S.; Kaeriyama, K J. Chem. Soc, Chem., Commun. 1986, 873; Jen, K.Y.; Miller, G.G.; Elsenbaumer, R.L J. Chem. Soc, Chem. Commun., 1986 1346; Elsenbaumer, R.L; Jen, K.Y.; Oboodi, R. Synth. Met, 1986, 15, 169
Havinga, E.E.; van Horssen, L.W. Makromol. Chem., Macromol. Symp., 1989, 24, 67.
Patil, A.O.; Ikenoue, Y.; Wudl, F.; Heeger, A.J. J. Am. Chem. Soc. 1987, 109, 1858
Patil, A.O.; Ikenoue, Y.; Basescu, N.; Colaneri, N.; Chen, J.; Wudl, F. Heeger, A.J., Synth. Met., 1987 20,151
Ikenoue, Y.; Chiang, J.; Patil, A.O.; Wudl, F.; Heeger, A.J.J. Am. Chem. Soc, 1988, 110, 2983.
Havinga, E.E.; van Horssen, L.W.; ten Hoeve, W.; Wynberg, H.; Meijer E.W. Polymer Bull. 1967, 18, 277; Havinga, E.E.; ten Hoeve, W.; Meijer, E.W.; Wynberg, H. Chem. Materials 1989, in press.
Naegele, D.; Bittihn, R. Solid State Ionics, 1988, 28–30, 983.
Okano, M.; Itoh, K.; Fujishima, A.; Honda, K, Chem. Lett., 1986, 469.
Kern, J.-M.; Sauvage, J.-P., J. Chem. Soc, Chem. Commun, 1989 657 Sigawa, H.; Shimidzu, T.; Honda, K. J. Chem. Soc, Chem. Commun. 1989, 132.
Mohammadi, A.; Hasan, M.-A.; Liedberg, B.; Lundstrom, I.; Salaneck, W.R. Synth. Met. 1986, 14, 189.
Meijer, E.W.; Nijhuis, S.; van Vroonhoven, F.C.B.M., J. Am. Chem. Soc., 1988, 110, 7209.
Azides and Nitrenes, Reactivity and Utility; Scriven, E.F.V.,Ed.; Academic Press: New York, 1984.
Horner, L.; Christmann, A.; Gross, A. Chem.Ber. 1963, 96, 399.
Reiser, A.; Leyshon, L.J. J.Am.Chem.Soc. 1971, 93, 4051.
Abramovitch, R.A.; Challand, S.R., Scriven, E.F.V. J.Am.Chem.Soc. 1972, 94, 1374.
Waddell, W.H.; Go, CL. J.Am.Chem.Soc. 1982, 104, 5804.
Leyva, E.; Platz, M.S.; Persy, G.: Wirz J. J.Am.Chem.Soc. 1986, 108, 3783.
Leyva, E.; Young, M.J.T.; Platz, M.S. J.Am.Chem.Soc. 1986, 108, 8307.
Schrock, A.K.; Schuster, G.B. J.Am.Chem.Soc. 1984, 106, 5228.
Chapman, O.L; Le Roux, J.P. J.Am.Chem.Soc. 1978, 100, 282.
Chapman, O.L; Sheridan, R.S.; Le Roux J.P. J.Am.Chem.Soc. 1978, 100, 6245.
Chapman, O.L.; Sheridan, R.S. J.Am.Chem.Soc. 1979, 101, 3690.
Chapman, O.L; Sheridan, R.S.; Le Roux, J.P. Reel.Trav.Chim. Pays — Bas 1979, 98, 334.
Shields, C.J.; Chrisope, DR.; Schuster, G.B.; Dixon, A.J.; Poliakoff, M.; Turner, J.J. J.Am.Chem.Soc. 1987, 109, 4723.
Lindsay, R.O.; Allen, C.F.H. Org. Synth. 1955, 3, 710
Smith, PAS.; Boyer, J.H. Org. Synth. 1963, 4, 75.
See for polyanilines: Green, A.G.; Woodhead, A.E. J.Chem.Soc. 1910, 101, 1117
Macdiarmid, A.G.; Chiang, J.-C; Huang, W.; Humphrey, B.D.; Somasiri, N.L.D. Mol.Cryst.Liq.Cryst. 1985, 115, 309.
Azuma, C; Dias, M.; Mano, E.B. Macromol. Chem., Macromol. Symp. 1986, 2, 169.
Schaap, A.P.; Zaklika, K.A., in Singlet Oxygen, Wasserman, H.H.; Murray, R.W., Eds., Academic Press, New York, 1970, p. 287.
Swager, T.M.; Grubbs, R.H. J. Am. Chem. Soc. 1987, 109, 894 and references therein.
Staring, E.G.J.; Meijer, E.W., manuscript in preparation.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1990 Kluwer Academic Publishers
About this chapter
Cite this chapter
Meijer, E.W., Nijhuis, S., Van Vroonhoven, F.C.B.M., Havinga, E.E. (1990). Poly-1,2-Azepines by the Photopolymerization of Phenyl Azides: A New Route to Processible Conducting Polymers. In: Brédas, J.L., Chance, R.R. (eds) Conjugated Polymeric Materials: Opportunities in Electronics, Optoelectronics, and Molecular Electronics. NATO ASI Series, vol 182. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2041-5_8
Download citation
DOI: https://doi.org/10.1007/978-94-009-2041-5_8
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-7416-2
Online ISBN: 978-94-009-2041-5
eBook Packages: Springer Book Archive