Chemical Oxidative Polymerization of 4-Amino-3-Hydroxynaphthalene-1-Sulfonic Acid and Its Salts

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New functional homopolymeric, semiconducting materials soluble in polar solvents, were synthesized by chemical oxidative polymerization of 4-amino-3-hydroxynaphthalene-1- sulfonic acid (AHNSA) and its salts, using ammonium peroxydisulfate as an oxidant, in water at room temperature. Polymerization products obtained from AHNSA, AHNSA hydrochloride, AHNSA mono-sodium salt and AHNSA di-sodium salt were characterized by elemental analysis, gel-permeation chromatography (GPC), infrared spectroscopy (IR) and conductivity measurements. Polymers of AHNSA salts have increased weight-average molecular weights and polydispersity index values, compared to AHNSA polymer. Molecular weights approach a maximum value of ~25200 for polymers of AHNSA salts. Elemental analysis data of polymeric samples show a decrease of the S/C ratio for all polymeric materials in comparison with the monomer, indicating considerable elimination of sulfonic acid group from the macromolecular structure during the polymerization process. New substitution patterns shown by IR spectroscopic analysis combined with MNDO-PM3 semi-empirical quantum mechanical calculations revealed N─C coupling reactions as dominant, where C belongs to unsubstituted AHNSA ring. Coupling mode N─C1 is also important. Naphthoquinonoid and benzenoid structures were observed by IR spectroscopy. Influence of pH on the AHNSA oxidative chemical polymerization mechanism was examined.

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Periodical:

Edited by:

Dragan P. Uskokovic, Slobodan K. Milonjic and Dejan I. Rakovic

Pages:

405-410

DOI:

10.4028/www.scientific.net/MSF.518.405

Citation:

G. Ćirić-Marjanović et al., "Chemical Oxidative Polymerization of 4-Amino-3-Hydroxynaphthalene-1-Sulfonic Acid and Its Salts", Materials Science Forum, Vol. 518, pp. 405-410, 2006

Online since:

July 2006

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$35.00

[1] A. Meneguzzi, M.C. Pham, J.C. Lacroix, B. Piro, A. Adenier, C.A. Ferreira and P.C. Lacaze: J. Electrochem. Soc. Vol. 148 (2001), p. B121.

[2] Y. Xu, Q. Xie, M. Hu, L. Nie and S. Yao: J. Electroanal. Chem. Vol. 389 (1995), p.85.

[3] B.K. Schmitz and W.B. Euler: J. Electroanal. Chem. Vol. 399 (1995), p.47.

[4] O.I. Aksimentyeva: Mol. Cryst. Liq. Cryst. Vol. 324 (1998), p.125.

[5] G. Ćirić-Marjanović, M. Trchová, P. Matějka, P. Holler, B. Marjanović and I. Juranić: React. Funct. Polymers (submitted for publication).

[6] G. Socrates: Infrared and Raman Characteristic Group Frequencies (John Wiley & Sons, New York 2001), p.78, 101, 107, 112, 122, 157.

[7] G. Ćirić-Marjanović, N. Cvjetićanin, S. Mentus, J. Budinski-Simendić and I. Krakovsky: Polym. Bull. Vol. 50 (2003), p.319.

DOI: 10.1007/s00289-003-0174-8

[8] L.J. Bellamy: The Infra-red Spectra of Complex Molecules (Richard Clay and Company, Ltd., Bungay, Suffolk 1962), pp.65-84, 249-261.

[9] D.L. Vien, N.B. Colthup, W.G. Fateley and J.G. Grasselli: The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules (Academic Press, Inc. San Diego 1991), p.44.

DOI: 10.1016/b978-0-08-057116-4.50009-2

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