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Synthesis of water-soluble conducting polypyrrole with transition-metal tetrasulfonated porphyrins

Mohammad Reza Nabid

Department of Chemistry, Faculty of Science, Shahid Beheshti University G.C., 1983963113 Tehran, Iran

Corresponding author, fax: +98 21-22403041.

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Mitra Shamsianpour

Department of Chemistry, Faculty of Science, Shahid Beheshti University G.C., 1983963113 Tehran, Iran

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Roya Sedghi

Department of Chemistry, Faculty of Science, Shahid Beheshti University G.C., 1983963113 Tehran, Iran

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Samira Osati

Department of Chemistry, Faculty of Science, Shahid Beheshti University G.C., 1983963113 Tehran, Iran

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, and

Nasser Safari

Department of Chemistry, Faculty of Science, Shahid Beheshti University G.C., 1983963113 Tehran, Iran

SPP full member in good standing.

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https://doi.org/10.1142/S1088424610001829Cited by:3 (Source: Crossref)

Abstract

A novel catalytic route for the synthesis of a water-soluble and electrically conducting polypyrrole (PPy) in the presence of sulfonated polystyrene (SPS) is presented. Anionic water-soluble transition-metal tetrasulfonated porphyrins (TSPP) were used to catalyze the polymerization. The reactions were carried out with different monomer, catalyst, template and initiator concentrations and the optimum conditions are reported. Also various pH values ranging from 1 to 4 were investigated. The absorbance of the polaron bands at different pH values demonstrates that pH 2 is the best condition for polymerization. Precipitation or "salting out" phenomenon was highly dependent on the mentioned factors. The formation of PPy was confirmed by UV-vis and FT-IR spectroscopy. Cyclic voltammetry (CV) showed that the synthesized polymer has convenient electroactivity. Furthermore, the presence of SPS that serves as a charge-compensating dopant in this complex provides a unique combination of properties such as processability and water solubility.

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References

R. Nagarajanet al., Macromolecules 33, 9542 (2000), DOI: 10.1021/ma000954+. Web of Science, Google Scholar
W. Liuet al., J. Am. Chem. Soc. 121, 71 (1999), DOI: 10.1021/ja982270b. Web of Science, Google Scholar
D. Kincalet al., Synth. Met. 92, 53 (1998), DOI: 10.1016/S0379-6779(98)80022-2. Web of Science, Google Scholar
H. H. Kuhn, A. D. Child and W. C. Kimbrell, Synth. Met. 71, 2139 (1995), DOI: 10.1016/0379-6779(94)03198-F. Web of Science, Google Scholar
A. Kaynak, Fibers Polym. 2, 171 (2001), DOI: 10.1007/BF02875341. Google Scholar
B. K. Anniset al., Synth. Met. 22, 191 (1988), DOI: 10.1016/0379-6779(88)90216-0. Web of Science, Google Scholar
F. F. Brunoet al., Biomacromolecules 7, 586 (2006), DOI: 10.1021/bm0506501. Web of Science, Google Scholar
V. Rumbauet al., Biomacromolecules 8, 315 (2007), DOI: 10.1021/bm060949z. Web of Science, Google Scholar
J. S. Dordick, M. A. Marletta and A. M. Klibanov, Biotechnol. Bioeng. 30, 31 (1987), DOI: 10.1002/bit.260300106. Web of Science, Google Scholar
J. A. Akkara, K. J. Senecal and D. L. Kaplan, J. Polym. Sci.: Polym. Chem. 29, 1561 (1991), DOI: 10.1002/pola.1991.080291105. Web of Science, Google Scholar
R. Ikeda, H. Uyama and S. Kobayashi, Macromolecules 29, 3053 (1996), DOI: 10.1021/ma951810b. Web of Science, Google Scholar
M. R. Nabid and A. A. Entezami, J. Appl. Polym. Sci. 94, 254 (2004), DOI: 10.1002/app.20882. Web of Science, Google Scholar
M. R. Nabidet al., Appl. Catal. A 328, 52 (2007). Web of Science, Google Scholar
Yu. Sakharovet al., Synth. Met. 142, 127 (2004), DOI: 10.1016/j.synthmet.2003.08.001. Web of Science, Google Scholar
J. A. Akkaraet al., Macromolecules 35, 2371 (2002). Google Scholar
S. Royet al., Biomacromolecules 3, 973 (2002), DOI: 10.1021/bm0255138. Google Scholar
X. Huet al., Synth. Met. 150, 1 (2005), DOI: 10.1016/j.synthmet.2004.11.006. Web of Science, Google Scholar
X. Huet al., React. Funct. Polym. 65, 239 (2005), DOI: 10.1016/j.reactfunctpolym.2005.06.007. Web of Science, Google Scholar
M. R. Nabidet al., J. Appl. Polym. Sci. 102, 2929 (2006), DOI: 10.1002/app.24034. Web of Science, Google Scholar
A. G. Macdiarmid and A. J. Epstein, ACS Symp. Ser. (Photonic and Optoelectronic Polymers)672 (1997) p. 395. Google Scholar
T. A. Skotheim , R. L. Elsenbaumer and J. R. Reynolds , Handbook of Conducting Polymers ( Marcel Dekker , New York , 1998 ) . Google Scholar
E. B. Fleischeret al., J. Am. Chem. Soc. 93, 3162 (1971), DOI: 10.1021/ja00742a012. Web of Science, Google Scholar
A. D. Adler and F. R. Long, J. Org. Chem. 32, 476 (1967), DOI: 10.1021/jo01288a053. Web of Science, Google Scholar
D. W. Thomas and A. E. A. Martell, J. Am. Chem. Soc. 81, 5111 (1959), DOI: 10.1021/ja01528a024. Web of Science, Google Scholar
D. M. Chen and Y. H. Zhang, Spectrochim. Acta A. 59, 87 (2003). Web of Science, Google Scholar
P. Wang and J. S. Dordick, Macromolecules 31, 941 (1998), DOI: 10.1021/ma971465l. Web of Science, Google Scholar
R. Premachandranet al., Chem. Mater. 9, 1342 (1997), DOI: 10.1021/cm960418p. Web of Science, Google Scholar
K. S. Alvaet al., Macromolecules 30, 4024 (1997), DOI: 10.1021/ma961544h. Web of Science, Google Scholar
D. Chin, G. N. Lamar and A. L. Balch, J. Am. Chem. Soc. 102, 5945 (1980), DOI: 10.1021/ja00538a059. Web of Science, Google Scholar
G. B. Streetet al., Mol. Cryst. Liq. Cryst. 83, 253 (1982), DOI: 10.1080/00268948208072174. Google Scholar
K. G. Neohet al., Chem. Mater. 8, 167 (1996), DOI: 10.1021/cm950312e. Web of Science, Google Scholar
M. Satohet al., Synth. Met. 84, 167 (1997), DOI: 10.1016/S0379-6779(97)80696-0. Web of Science, Google Scholar
A. Watanabe, M. Tanaka and J. Tanaka, Chem. Soc. Jpn. 54, 2278 (1981), DOI: 10.1246/bcsj.54.2278. Web of Science, Google Scholar
J. E. Mark , Polymer Data Handbook ( Oxford University Press , Oxford , 1999 ) . Google Scholar
J. L. Bredas and G. B. Street, Acc. Chem. Res. 18, 309 (1985), DOI: 10.1021/ar00118a005. Web of Science, Google Scholar