Synthesis and Characterization of Poly(N-Methyl isoindole): A Soluble Conducting Polymer

Rhee SB; Lee MH; Moon BS; Kang Y

Korea Polymer Journal, Vol.1, No.1, 61-68, April, 1993

A soluble conducting polymer, poly(N-methyl isoindole), was prepared by chemical and electrochemical oxidation of N-methyl isoindole. The polymer structure was proposed from the IR and elemental analyses. The conductivity of the polymer was measured to be in the range of 10^-6-10^-4S/cm depending on the extent of doping. The electrochemical properties were also studied by examining the cyclovoltammographs of the polymer. This polymer was soluble in DMF or DMSO, and the electrochemical properties of the solution cast film were almost identical to those of the film freshly prepared. Furthermore, poly(N-methyl isoindole) showed good electrochromic property by changing its color from golden yellow in reduced state to dark green in oxidized state. We have prepared a unique electrochemical UV cell to study the in situ spectroelectrochemical properties of poly(N-methyl isoindole).

[References]

Diaz AF, Kanazawa KK, Gardini GP, J. Chem. Soc.-Chem. Commun., 1979, 635 (1990)
Waltman RJ, Bargow J, Diaz AF, J. Phys. Chem., 87, 1459 (1983)
Tourillon G, Garmer F, J. Electroanal. Chem., 135, 173 (1983)
Satoh M, Kaneto K, Yoshino K, J. Chem. Soc.-Chem. Commun., 1984, 1627 (1984)
Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger AJ, J. Chem. Phys., 82(12), 15 (1985)
Chandrasekhar P, Masulaitis AM, Gumbs RW, Synth. Met., 36, 303
Yoshida H, Uotani N, Saida Y, PCT Int. Appl. WO 87 03, 607 (ref. CA 108: 38976)
Perrin DD, Armarego WLF, Perrin OR, Purification of Laboratory Chemicals, 2nd Ed., Pergamon Press (1982)
Wittig VG, Gloss G, Mindermann F, Ann. Chem., 594, 89 (1955)
Valdes LB, Proc. I-R-E, 420 (1954)
Brewster JH, Fusco AM, Carosino LE, Corman BG, J. Org. Chem., 28, 498 (1963)
Bruce J, Challenger F, Gibson HB, Allenby WE, J. Inst. Pet., 34, 226 (1984)
Wudl F, Kobayashi M, Heeger A, Eur. Patent, Appl. No. 0164972 (1985)
Wudl F, Kobayashi M, Heeger A, J. Org. Chem., 49, 3382 (1984)
Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger AJ, J. Chem. Phys., 82(12), 5717 (1985)
Aldissi M, Synth. Met., 13, 87 (1986)
Elsenbaumer RL, Jen KY, Oboodi R, Synth. Met., 15, 169 (1986)
Feast WJ, Millichamp IS, Friend RH, Horton ME, Phillips D, Rughooputh SDDV, Street GB, Synth. Met., 10, 181 (1985)
Hotta S, Rughooputh SDDV, Heeger AJ, Synth. Met., 22, 79 (1987)

[Referenced By]

[1] Diaz AF, Kanazawa KK, Gardini GP, J. Chem. Soc.-Chem. Commun., 1979, 635 (1990)

[2] Waltman RJ, Bargow J, Diaz AF, J. Phys. Chem., 87, 1459 (1983)

[3] Tourillon G, Garmer F, J. Electroanal. Chem., 135, 173 (1983)

[4] Satoh M, Kaneto K, Yoshino K, J. Chem. Soc.-Chem. Commun., 1984, 1627 (1984)

[5] Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger AJ, J. Chem. Phys., 82(12), 15 (1985)

[6] Chandrasekhar P, Masulaitis AM, Gumbs RW, Synth. Met., 36, 303

[7] Yoshida H, Uotani N, Saida Y, PCT Int. Appl. WO 87 03, 607 (ref. CA 108: 38976)

[8] Perrin DD, Armarego WLF, Perrin OR, Purification of Laboratory Chemicals, 2nd Ed., Pergamon Press (1982)

[9] Wittig VG, Gloss G, Mindermann F, Ann. Chem., 594, 89 (1955)

[10] Valdes LB, Proc. I-R-E, 420 (1954)

[11] Brewster JH, Fusco AM, Carosino LE, Corman BG, J. Org. Chem., 28, 498 (1963)

[12] Bruce J, Challenger F, Gibson HB, Allenby WE, J. Inst. Pet., 34, 226 (1984)

[13] Wudl F, Kobayashi M, Heeger A, Eur. Patent, Appl. No. 0164972 (1985)

[14] Wudl F, Kobayashi M, Heeger A, J. Org. Chem., 49, 3382 (1984)

[15] Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger AJ, J. Chem. Phys., 82(12), 5717 (1985)

[16] Aldissi M, Synth. Met., 13, 87 (1986)

[17] Elsenbaumer RL, Jen KY, Oboodi R, Synth. Met., 15, 169 (1986)

[18] Feast WJ, Millichamp IS, Friend RH, Horton ME, Phillips D, Rughooputh SDDV, Street GB, Synth. Met., 10, 181 (1985)

[19] Hotta S, Rughooputh SDDV, Heeger AJ, Synth. Met., 22, 79 (1987)