Nucleophilic substitution reactions of polyaniline with substituted benzenediazonium ions: A facile method for controlling the surface chemistry of conducting polymers

Chemistry of Materials

Volumn 8, Issue 6, 1996, Pages 1164-1166

  Liu, Gang ^a   Freund, Michael S ^a  

^a LEHIGH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001054535     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm9601502     Document Type: Article

References (35)

1. For examples of the use of conducting polymers in electronic devices, see: Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988, 335, 137-141. Sailor, M. J.; Ginsburg, E. J.; Gorman, C. B.; Kumar, A.; Grubbs, R. H.; Lewis, N. S. Science 1990, 249, 1146-1149. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477-479. Zhang, C.; Hoger, S.; Pakbaz, K.; Wudl, F.; Hegger, A. J. J. Electron Mater. 1994, 23, 453-458.
2. For examples of the use of conducting polymers in electronic devices, see: Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988, 335, 137-141. Sailor, M. J.; Ginsburg, E. J.; Gorman, C. B.; Kumar, A.; Grubbs, R. H.; Lewis, N. S. Science 1990, 249, 1146-1149. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477-479. Zhang, C.; Hoger, S.; Pakbaz, K.; Wudl, F.; Hegger, A. J. J. Electron Mater. 1994, 23, 453-458.
3. For examples of the use of conducting polymers in electronic devices, see: Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988, 335, 137-141. Sailor, M. J.; Ginsburg, E. J.; Gorman, C. B.; Kumar, A.; Grubbs, R. H.; Lewis, N. S. Science 1990, 249, 1146-1149. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477-479. Zhang, C.; Hoger, S.; Pakbaz, K.; Wudl, F.; Hegger, A. J. J. Electron Mater. 1994, 23, 453-458.
4. For examples of the use of conducting polymers in electronic devices, see: Burroughes, J. H.; Jones, C. A.; Friend, R. H. Nature 1988, 335, 137-141. Sailor, M. J.; Ginsburg, E. J.; Gorman, C. B.; Kumar, A.; Grubbs, R. H.; Lewis, N. S. Science 1990, 249, 1146-1149. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477-479. Zhang, C.; Hoger, S.; Pakbaz, K.; Wudl, F.; Hegger, A. J. J. Electron Mater. 1994, 23, 453-458.
5. For examples of the use of conducting polymers in energy storage devices, see: Gratzel, M. Energy Resources through Photochemistry and Catalysis; Academic Press: New York, 1983. Conway, B. E. J. Electrochem. Soc. 1991, 138, 1539-1548. Geniès, E. M. New J. Chem. 1991, 15, 373-377. Li, F. B.; Albery, W. J. J. Electroanal. Chem. 1991, 302, 279-284.
6. For examples of the use of conducting polymers in energy storage devices, see: Gratzel, M. Energy Resources through Photochemistry and Catalysis; Academic Press: New York, 1983. Conway, B. E. J. Electrochem. Soc. 1991, 138, 1539-1548. Geniès, E. M. New J. Chem. 1991, 15, 373-377. Li, F. B.; Albery, W. J. J. Electroanal. Chem. 1991, 302, 279-284.
7. For examples of the use of conducting polymers in energy storage devices, see: Gratzel, M. Energy Resources through Photochemistry and Catalysis; Academic Press: New York, 1983. Conway, B. E. J. Electrochem. Soc. 1991, 138, 1539-1548. Geniès, E. M. New J. Chem. 1991, 15, 373-377. Li, F. B.; Albery, W. J. J. Electroanal. Chem. 1991, 302, 279-284.
8. For examples of the use of conducting polymers in energy storage devices, see: Gratzel, M. Energy Resources through Photochemistry and Catalysis; Academic Press: New York, 1983. Conway, B. E. J. Electrochem. Soc. 1991, 138, 1539-1548. Geniès, E. M. New J. Chem. 1991, 15, 373-377. Li, F. B.; Albery, W. J. J. Electroanal. Chem. 1991, 302, 279-284.
9. For examples of the use of conducting polymers in catalytic reactions, see: Andrieux, C. P.; Dumasbouchiat, J. M.; Savéant, J. M. J. Electroanal. Chem. 1982, 131, 1-35. Bull, R. A.; Fan, F. R.; Bard, A. J. J. Electrochem. Soc. 1983, 130, 1636-1638. Hable, C. T.; Wrighton, M. S. Langmuir 1993, 9, 3284-3290.
10. For examples of the use of conducting polymers in catalytic reactions, see: Andrieux, C. P.; Dumasbouchiat, J. M.; Savéant, J. M. J. Electroanal. Chem. 1982, 131, 1-35. Bull, R. A.; Fan, F. R.; Bard, A. J. J. Electrochem. Soc. 1983, 130, 1636-1638. Hable, C. T.; Wrighton, M. S. Langmuir 1993, 9, 3284-3290.
11. For examples of the use of conducting polymers in catalytic reactions, see: Andrieux, C. P.; Dumasbouchiat, J. M.; Savéant, J. M. J. Electroanal. Chem. 1982, 131, 1-35. Bull, R. A.; Fan, F. R.; Bard, A. J. J. Electrochem. Soc. 1983, 130, 1636-1638. Hable, C. T.; Wrighton, M. S. Langmuir 1993, 9, 3284-3290.
12. For examples of the use of conducting polymers in sensors, see: Josowicz, M.; Janata, J. Anal. Chem. 1986, 58, 514-517. Heller, A. J. Phys. Chem. 1992, 96, 3579-3587. Gardner, J. W.; Bartlett, P. N. Synth. Met. 1993, 57, 3665-3670. Kuwabata, S.; Martin, C. R. Anal. Chem. 1994, 66, 2757-2762. Freund, M. S.; Lewis, N. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2652-2656.
13. For examples of the use of conducting polymers in sensors, see: Josowicz, M.; Janata, J. Anal. Chem. 1986, 58, 514-517. Heller, A. J. Phys. Chem. 1992, 96, 3579-3587. Gardner, J. W.; Bartlett, P. N. Synth. Met. 1993, 57, 3665-3670. Kuwabata, S.; Martin, C. R. Anal. Chem. 1994, 66, 2757-2762. Freund, M. S.; Lewis, N. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2652-2656.
14. For examples of the use of conducting polymers in sensors, see: Josowicz, M.; Janata, J. Anal. Chem. 1986, 58, 514-517. Heller, A. J. Phys. Chem. 1992, 96, 3579-3587. Gardner, J. W.; Bartlett, P. N. Synth. Met. 1993, 57, 3665-3670. Kuwabata, S.; Martin, C. R. Anal. Chem. 1994, 66, 2757-2762. Freund, M. S.; Lewis, N. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2652-2656.
15. For examples of the use of conducting polymers in sensors, see: Josowicz, M.; Janata, J. Anal. Chem. 1986, 58, 514-517. Heller, A. J. Phys. Chem. 1992, 96, 3579-3587. Gardner, J. W.; Bartlett, P. N. Synth. Met. 1993, 57, 3665-3670. Kuwabata, S.; Martin, C. R. Anal. Chem. 1994, 66, 2757-2762. Freund, M. S.; Lewis, N. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2652-2656.
16. For examples of the use of conducting polymers in sensors, see: Josowicz, M.; Janata, J. Anal. Chem. 1986, 58, 514-517. Heller, A. J. Phys. Chem. 1992, 96, 3579-3587. Gardner, J. W.; Bartlett, P. N. Synth. Met. 1993, 57, 3665-3670. Kuwabata, S.; Martin, C. R. Anal. Chem. 1994, 66, 2757-2762. Freund, M. S.; Lewis, N. S. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2652-2656.
17. For examples of the use of conducting polymers in biochemical applications, see: Miller, L. L. Mol. Cryst. Liq. Cryst. 1988, 160, 297-301. Lotan, N.; Ashkenazi, G.; Tuchman, S.; Nehamkin, S.; Sideman, S. Mol. Cryst. Liq. Cryst. 1993, 234, 635-644.
18. For examples of the use of conducting polymers in biochemical applications, see: Miller, L. L. Mol. Cryst. Liq. Cryst. 1988, 160, 297-301. Lotan, N.; Ashkenazi, G.; Tuchman, S.; Nehamkin, S.; Sideman, S. Mol. Cryst. Liq. Cryst. 1993, 234, 635-644.
19. Diaz, A. F.; Bargon, J In Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986; Vol. 1; pp 81-115.
20. 8
21. LaCroix, J. C.; Diaz, A. F. J. Electrochem. Soc. 1988, 136, 1457-1463.
22. Salmon, M.; Saloma, M.; Bidan, G.; Geniès, E. M. Electrochim. Acta 1989, 34, 117-120.
23. Geniès, E. M.; Noel, P. J. Electroanal. Chem. 1991, 310, 89-111.
24. Wolf, M. O.; Wrighton, M. S. Chem. Mater. 1994, 6, 1526-1533.
25. McCoy, C. H.; Lorkovic, I. M.; Wrighton, M. S. J. Am Chem. Soc. 1995, 117, 6934-6933.
26. Torres, W.; Fox, M. A. Chem. Mater. 1992, 4, 146-152.
27. Zollinger, H. Diazo Chemistry I: Aromatic and Heteroaromatic Compounds; VCH Publishers: New York, 1994.
28. -2 from a solution containing 0.25 M aniline and 1.0 M sulfuric acid. Films were reduced at -0.20 V versus Ag/AgCl for 5 min prior to exposure to solutions containing diazonium ions.
29. ls were 1 and 1.8, respectively.
30. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; John Wiley & Sons: New York, 1980; pp 569-573.
31. -1) gave the following linear regressions: unmodified polymer film (slope = 0.97 ± 0.03; intercept = 1.69 ± 0.05; R = 0.997; n = 10); modified film (slope = 0.96 ± 0.02; intercept = 1.58 ± 0.04; R = 0.998; n = 10).
32. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; John Wiley & Sons: New York, 1980; pp 127-130.
33. Moulder, J. F; Stickle, W. F.; Sobol, P. E.; Bomben, K. D. Handbook of X-ray Photoelectron Spectroscopy; Perkin-Elmer Corp., Physical Electronics Division: Eden Prairie, MN, 1992.
34. Swain, C. G.; Sheats, J. E.; Harbison, K. G. J. Am. Chem. Soc. 1975, 97, 783.
35. DeArmitt, C ; Armes, S. P.; Winter, J.; Uribe, F. A.; Gottesfeld, S.; Mombourquette, C. Polymer 1993, 34, 158-162.