Skip to main content
SpringerLink
Log in
Book cover

Conducting Polymers pp 47–63Cite as

Conductive Complexes of Novel Porphyrin and Phenothiazine Polymer Systems

  • Conference paper

  • 301 Accesses

Abstract

Charge transfer complexes of porphyrins, phthalocyanines and phenothiazines have desirable electrical conductive properties. The parent compounds can also function as polymer precursors which in the past often suffered from poor solubility characteristics, limiting their utility in further chemical reactions. Recently, the synthesis of highly soluble metallotetrabenzporphyrin and phenothiazine homologs has made it possible to study the charge transfer characteristics of those compounds and their complexes in a variety of solvents. We wish to report on alternating and direct current measurements of some metal mesophenyltetrabenzporphyrins, phenothiazinyls, their iodine and TCNQ complexes in the solid and solution state, and ternary complexes of these compounds with polyvinylpyridine. An iodine:phenothiazine-ionene dimer complex exhibited an unusual stoichiometry, and has the lowest resistivity so far detected in iodine-ionene polymers. Well-defined ternary complexes of metallo-organics, I2 and polyvinylpyridines have markedly lower resistivities and activation energies than the parent compounds or the dual component complexes. The structure/conductivity relationship of several of the complexes and ternary polymeric models are discussed.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. S.F. Fischer et al., Bull. Amer. Phys. Soc., 24, 346 (1979).

    Google Scholar 

  2. N. Karl, Pr. Nauk. Inst. Chem. Org. Fiz. Politech. Wroclaw, 16, 43 (1978).

    CAS  Google Scholar 

  3. R. J. P. Williams, Current Topics in Bioenergetics, 3, 79 (1969).

    Google Scholar 

  4. J. Mordclewski and W. E. Geiger, J. Am. Chem. Soc., 100, 7429 (1978).

    Article  Google Scholar 

  5. A. Van Heuvelen, J. Biol. Phys., 1, 215 (1973).

    Article  Google Scholar 

  6. H. Siegel and C. F. Naumann, J. Am. Chem. Soc., 98, 730 (1976)

    Article  Google Scholar 

  7. H. Siegel and P. E. Amisler, ibid., 98, 7390 (1976)

    Google Scholar 

  8. H. Siegel et al., Inorg. Chem., 16, 790 (1977)

    Article  Google Scholar 

  9. E. C. Johnson et al., Caned. J. Chem., 56, 1381 (1978)

    Article  CAS  Google Scholar 

  10. P. R. Mitchell and H. Siegel, J. Amer. Chem. Soc., 100, 1564 (1978)

    Article  CAS  Google Scholar 

  11. P. R. Mitchell and H. Siegel, Helv. Chim. Acta, 62, 1723 (1979)

    Article  CAS  Google Scholar 

  12. C. R. Naumann and H. Siegel, FEBS Lett., 47, 122 (1974)

    Article  CAS  Google Scholar 

  13. P. Chaudhuri and H. Siegel, J. Amer. Chem. Soc., 97, 3209 (1975); 99, 3242 (1977)

    Article  Google Scholar 

  14. H. Siegel et al., Europ. J. Biochem., 41, 290 (1974)

    Google Scholar 

  15. G. Cilento, Quart. Revs. Biophys., 6, 488 (1973)

    Google Scholar 

  16. Y. Fukuda, P. R. Mitchell and H. Siegel, Helv. Chim. Acta, 61, 638 (1978)

    Article  CAS  Google Scholar 

  17. H. Siegel et al., Biochim. Biophys. Acta, 148, 655 (1967)

    Google Scholar 

  18. H. Siegel and P. E. Amsler,ibid., 98, 7390, (1976)

    Google Scholar 

  19. A. M. Golub, Russ. Chem. Revs, 45, 479 (1976)

    Article  Google Scholar 

  20. R. Clement et al., J. Chem. Soc. Chem. Commun., 654 (1974)

    Google Scholar 

  21. A. N. Nesmeyanov et al., Dokl. Nauk, SSSR, 221, 229 (1975)

    Google Scholar 

  22. P. Pasman et al., Chem. Phys. Lett., 59, 398 (1978)

    Article  Google Scholar 

  23. L. M. Titvinenko et al., Russ. Chem. Revs, 44, 718 (1975).

    Article  Google Scholar 

  24. H. Bretschneider, Wiss. Z. Tech. Hochschule Karl Marxstadt, 17, 281 (1975)

    Google Scholar 

  25. F. Cramer, Einschlussverbindungen, Springer, Heidelberg (1974).

    Google Scholar 

  26. Y. Matsunaga et al., Bull. Chem. Soc. Japan, 47, 2826 (1974).

    Google Scholar 

  27. M. Mohwald, Chem. Phys. Lett., 26, 509 (1974).

    Article  Google Scholar 

  28. H. Siegel and D. B. McCormick., J. Am. Chem. Soc., 93, 2041 (1971).

    Article  Google Scholar 

  29. V. Hadek, H. Noguchi and A. Rembaum, Macromolecules, 4, 494 (1971).

    Article  Google Scholar 

  30. A. T. Florence, in Micellization, Solubilization and Microemulsions (K. L. Mittal, ed.) Plenum Press, New York (1977), Vol. 1.

    Google Scholar 

  31. P. K. Dea and H. Keyzer in Modern Bioelectrochemistry (F. Gutmann and H. Keyzer, eds.), Plenum Press, New York (1986).

    Google Scholar 

  32. T. E. Phillips, B. M. Hoffman, J. Amer. Chem. Soc., 99:23, 7734 (1977).

    Google Scholar 

  33. J. L. Peterson, C. S. Schramm, D. R. Stojakovic, B. M. Hoffman, T. J. Marks, J. Amer. Chem. Soc., 99:1, 286 (1977).

    Google Scholar 

  34. S. K. Wright, C. J. Schramm, T. E. Phillips, D. M. Scholler, B. M. Hoffman, Synthetic Metals, 1, 43 (1979).

    Google Scholar 

  35. T. E. Phillips, R. P. Scaringe, B. M. Hoffman, J. A. Ibers, J. Amer. Chem. Soc., 102:10, 3435 (1980).

    Google Scholar 

  36. J. Martinsen, L. J. Pace, T. E. Phillips, B. M. Hoffman and J. A. Ibers, J. Amer. Chem. Soc., 104, 83 (1982).

    Article  CAS  Google Scholar 

  37. W. B. Euler, J. Martinsen, L. J. Pace, B. M. Hoffman and J. A. Ibers, Mol. Cryst. Liq. Cryst., 81, 949, 231 (1982).

    CAS  Google Scholar 

  38. B. M. Hoffman and J. A. Ibers, Acc. Chem. Res., 16, 15 (1983).

    Article  CAS  Google Scholar 

  39. T. Inabe, S. Nakamura, W. Liang and T. J. Marks, J. Amer. Chem Soc., 107 7224 (1985).

    Google Scholar 

  40. J. Metz. and M. Hanack, J. Amer. Chem. Soc., 105, 828 (1983).

    Article  CAS  Google Scholar 

  41. M. Hanack, Israel J. Chem., 25, 205 (1985).

    CAS  Google Scholar 

  42. P. G. Wright, P. Stein, J. M. Burke and T. G. Spiro, J. Amer. Chem. Soc., 101 3531 (1979).

    Article  CAS  Google Scholar 

  43. G. Geib and H. Keyzer, In press.

    Google Scholar 

  44. I. Cozlan et al., J. Heterocyclic Chem., 21, 613 (1984).

    Article  Google Scholar 

  45. E. A. Nodiff and A. Cantor, “Phenothiazine Sulfides,” U.S. Patent; 4,155,874, May 22, 1979.

    Google Scholar 

  46. e.g., H. Noguchi and A. Rembaum, Polymer Letters, 7, 383 (1969).

    Article  CAS  Google Scholar 

  47. K. G. Reimer and C. B. Rose, In Press. A. S. Nelson and S. P. Gottfried J. Amer. Chem. Soc., 63, 487 (1941).

    Article  Google Scholar 

  48. K. G. Reimer, D. Sensharma, J. Wells, In Prep.

    Google Scholar 

  49. P. A. Barrett, D. A. Frye and R. P. Linstead, J. Chem. Soc., 1157 (1938).

    Google Scholar 

  50. F. Gutmann and H. Keyzer, Electrochim. Acta, 11, 1163 (1966).

    Article  CAS  Google Scholar 

  51. H. Keyzer and S. Maurer, In Prep.

    Google Scholar 

  52. F. Gutmann, H. Keyzer and L. E. Lyons, Organic Semiconductors. Part B Robert E. Krieger Publishing Co., Malabar, Florida (1983).

    Google Scholar 

  53. A. Rembaum, Encyclopedia of Polymer Sci. and Technol., 11, 318 (1968)

    Google Scholar 

  54. Wiley, N.Y., 1969; V. Hadek et al., Makromolecules, 4, 494 (1971).

    Google Scholar 

  55. J. M. Bruce and J. R. Henson, Polymer, 8, 619 (1967).

    Article  CAS  Google Scholar 

  56. H. Keyzer, unpublished results.

    Google Scholar 

  57. F. Gutmann and H. Keyzer, Electrochim. Acta, 11, 555 (1966).

    Article  CAS  Google Scholar 

  58. S. Chan, C. M. Gooley and H. Keyzer, Tetrahedron Lett., 13, 1193 (1975).

    Article  Google Scholar 

  59. F. Gutmann and H. Keyzer, J. Chem. Phys., 46, 1969 (1967).

    Article  CAS  Google Scholar 

  60. J. W. Summers and M. H. Litt, J. Polym. Sci., Polym. Chem. Ed., 11, (6), 1379 (1973).

    Google Scholar 

  61. D. S. Becker and R. G. Hayes, Inorg. Chem., 22, 3050 (1983).

    Article  CAS  Google Scholar 

  62. C. S. Schramm, R. P. Scaringe, Dr. R. Stojakovic, B. M. Hoffman,J. A. Ibers and T. J. Marks, J. Am. Chem. Soc., 102, 6702 (1980).

    Article  CAS  Google Scholar 

  63. L. J. Pace, A. Ulman and J. A. Ibers, Inorg. Chem., 21, 199 (1982).

    Article  CAS  Google Scholar 

  64. H. C. Freeman, J. Proc. Royal Soc. N.S.W., 112, 60 (1979).

    Google Scholar 

  65. V. Hadek and K. Ulbert, Rev. Sci. Instr., 38, 991 (1967).

    Article  Google Scholar 

  66. V. Hadek, J. Chem. Phys., 49, 5202 (1968).

    Article  CAS  Google Scholar 

  67. J. Tamamura and T. Yamane, Bull. Chem. Soc. Japan, 47, (4), 832 (1974).

    Article  CAS  Google Scholar 

  68. J. C. A. Boeyens and I. H. Herbstein, J. Phys. Chem., 69, 2160 (1965).

    Article  CAS  Google Scholar 

  69. J. H. Torrance and B. D. Silverman, Phys. Rev. B, 15, (2) 788 (1977).

    Article  CAS  Google Scholar 

  70. H. A. Staab et al., Angew. Chemie Int. Ed., (Engl.), 16, 801 (1977).

    Google Scholar 

  71. H. Werner, Angew. Chem., 89, 1 (1977); Angew. Chem. Int. Ed. (Engl), 16, (1977).

    Google Scholar 

  72. D. Braun and H. J. Sterzel, Ber. Bunsen Ges. Phys. Chem., 76, 551 (1972).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, California State University, Los Angeles, 5151 State University Drive, Los Angeles, California, 90032, USA

    G. Geib, H. Keyzer & K. G. Reimer

Authors
  1. G. Geib
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. Keyzer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. G. Reimer
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Chemistry Department, Instituto Superior Técnico, Lisbon, Portugal

    Luis Alcácer

Rights and permissions

Reprints and permissions

Copyright information

© 1987 D. Reidel Publishing Company, Dordrecht, Holland

About this paper

Cite this paper

Geib, G., Keyzer, H., Reimer, K.G. (1987). Conductive Complexes of Novel Porphyrin and Phenothiazine Polymer Systems. In: Alcácer, L. (eds) Conducting Polymers. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3907-3_3

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-3907-3_3

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8234-1

  • Online ISBN: 978-94-009-3907-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation