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http://dx.doi.org/10.12989/amr.2012.1.4.299

Synthesis, chemically and electrochemically polymerization of N-substituted pyrrole containing azo chromophore and its copolymerization with pyrrole  

Hosseini, Seyed Hossein (Department of Chemistry, Faculty of Science, Islamic Azad University)
Publication Information
Advances in materials Research / v.1, no.4, 2012 , pp. 299-310 More about this Journal
Abstract
This article describes the synthesis of a novel N-substituted pyrrole monomer containing an azobenzene group. The 2-[N-ethyl-N-[4-[(4-nitrophenyl) azo]-phenyl] amino] ethyl-3-chloropropionate (RedII) compound was synthesized via reaction of 4-nitro-4'-[N-ethyl-N-(2-hydroxyethyl)-amino] azobenzene (RedI) and 3-chloropropionic acid. RedII was reacted with the potassium salt of pyrrole then 2-[N-ethyl-N-[4-[(nitro phenyl) azo] phenyl] amino] ethyl-N-pyrrolyl propionate (Py-RedII) was prepared. Chemical polymerization of Py-RedII and copolymerization of Py-RedII with pyrrole carried out using $FeCl_3$. Poly (2-[N-ethyl-N-[4-[(nitro phenyl) azo] phenyl] amino] ethyl-N-pyrrolyl propionate) (PPy-RedII) was characterized by UV, IR, $^1HNMR$, $^{13}CNMR$ spectroscopies. Electropolymerization of Py-RedII and electroco-polymerization of Py-RedII and pyrrole were studied using conventional three electrodes system, Ag/AgCl reference electrode, platinum counter electrode and GC disk working electrode. Scanning electron microscopy (SEM), thermogravimetry analysis (TGA) and differential scanning calorimetry (DSC) were used for thermal and rheological studies. The TGA curve of PPy-RedII demonstrated a high thermal stability up to 200°C and its DSC thermogram showed two endothermic peaks at 88 and $122^{\circ}C$. The glass transition temperature of the polymer was found to be above the room temperature. Electrical conductivities of PPy-RedII and it's copolymer with pyrrole (PPy-RedII-co-Py) were studied by the four-probe method and produced conductivities of $7.5{\times}10^{-4}$ and $6.5{\times}10^{-3}Scm^{-1}$, respectively.
Keywords
azo polymers; conductivity; liquid crystals polymers; polypyrroles;
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1 Hosseini, S.H., Mohseni, S.H., Asadnia, A. and Kerdari, H. (2011), "Synthesis and microwave absorbing properties of polyaniline/$MnFe_2O_4$ nanocomposite", J. Alloy. Compd., 509(14), 4682-4687.   DOI   ScienceOn
2 Hosseini, S.H. and Asadnia, A. (2012), "Synthesis, characterization, and microwave-absorbing properties of polypyrrole/$MnFe_2O_4$ nanocomposite", J. Nanomater., 2012, 1-6.
3 Kiani, G.R., Arsalani, N., Hosseini, M.G. and Entezami, A.A. (2008), "Improvement of the conductivity, electroactivity, and redoxability of polythiophene by electropolymerization of thiophene in the presence ofcatalytic amount of 1-(2-pyrrolyl)-2-(2-thienyl) ethylene (PTE)", J. Appl. Polym. Sci., 108(4), 2700-2706.   DOI   ScienceOn
4 Kurihara, M. and Nishihara, M. (2002), "Azo- and quinone-conjugated redox complexes photo- and protoncoupled intramolecular reactions based on d-π interaction", Coord. Chem. Rev., 226(1-2), 125-135.   DOI   ScienceOn
5 Langley, P.J., Davis, F.J. and Mitchell, G.R. (1997), "Approaches to 1,1-disubstituted cinnolin-3-ylio oxides: synthesis and reactivity of a new class of heterocyclic betaines", J. Chem. Soc. Perkin. Trans., 2, 2229-2236.
6 Levesque, I. and Leclerc, M. (1997), "Novel dual-photochromism in polythiophene derivatives", Macromolecules, 30(15), 4347-4352.   DOI   ScienceOn
7 Liu, Y.C. and Tsai, C.J. (2003), "Stabilities of electropolymerized polypyrrole with caprolactam-modified clay", Chem. Mater., 15(1), 320-326.   DOI   ScienceOn
8 Mohr, G.J. and Grummt, U.W. (2004), "Photochemistry of the amine-sensor dye 4-N,N-dioctylamino-4-trifluoroacetylazobenzene", J. Photoch. Photobio. A, 163(3), 341-345.   DOI   ScienceOn
9 Munoz, E., Heras, M.A., Colina, A., Ruiz, V. and Lopez, P. (2007), "Electropolymerization of aniline on polyaniline-modified electrodes under hydrodynamic conditions", Electrochim. Acta, 52(14), 4778-4783.   DOI   ScienceOn
10 Pron, A. and Rannou, P. (2002), "Processible conjugated polymers: from organic semiconductors to organic metals and superconductors", Prog. Polym. Sci., 27(1), 135-190.   DOI   ScienceOn
11 Salaneck, W.R. (1991), "Science and application of conducting polymers", Proc of the 6th Europhysics industrial workshop, Adam Hilger.
12 Yousefi, M., Hosseini, S.H., Amani, V. and Khavasi, H.R. (2008), "(E)-2-{N-Ethyl-4-[(4-nitrophenyl)diazenyl]aniline} ethyl acrylate", Acta Cryst, E64, o789.
13 Cai, Z., Geng, M. and Tang, Z. (2004), "Novel battery using conducting polymers: Polyindole and polyaniline as active materials", J. Mater. Sci., 39(12), 4001-4003.   DOI
14 Zakerhamidi, M.S., Keshavarz, M., Tajalli, H., Ghanadzadeh, A., Ahmadi, S., Moghadam, M., Hosseini, S.H. and Hooshangi, V. (2010), "Isotropic and anisotropic environment effects on the UV/vis absorption spectra of three disperse azo dyes", J. Mol. Liq., 154(2-3), 94-101.   DOI   ScienceOn
15 Bradly, D.D.C. (1991), "Science and applications of conducting polymers", Chem Br, 8, 719-723.
16 Bryce, M.R., Chissel, A.D. and Smith, N.R.M. (1988), "Synthesis and cyclic voltammetric behaviour of some 3-substituted thiophenes and pyrroles: precursors for the preparation of conducting polymers", Synthetic Met., 26(2), 153-168.   DOI   ScienceOn
17 Campbell, S.A., Li, Y., Breakspear, S., Walsh, F.C. and Smith, J.R. (2007), "Conducting polymer coatings in electrochemical technology, Part 1 - Synthesis and fundamental aspects", T. I. Met. Finish., 85(5), 237-244.   DOI   ScienceOn
18 Carrasco, P.M., Grande, H.J., Cortazar, M., Alberdi, J.M., Areizaga, J. and Pomposo, J.A. (2006), "Structure-conductivity relationships in chemical polypyrroles of low, medium and high conductivity", Synthetic Met. 156(5-6), 420-425.   DOI   ScienceOn
19 Haynes, A.S. and Gouma, P.I. (2008), "Electrospun conducting polymer-based sensors for advanced pathogen detection", IEEE Sens. J., 8(6), 701-770.   DOI
20 Hosseini, S.H. and Entezami, A.A. (2000), "Poly(3-Methoxyethoxythiophene and its copolymers with aniline, thiophene and pyrrole: Chemical and electrochemical synthesis", Iran. Polym. J., 9(4), 255-261.
21 Hosseini, S.H. and Entezami, A.A. (2001), "Chemical and electrochemical synthesis of polymer and copolymers of 3-methoxyethoxythiophene with aniline, thiophene, pyrrole and studies of their gas and vapor sensing", Polym. Advan. Technol., 12(9), 524-534.   DOI   ScienceOn
22 Ansari, R., Falah Delavar, A. and Mohammad-khah, A. (2012), "Solid state ion selective electrode based on polypyrrole conducting polymer nanofilm as a new potentiometric sensor for Zn2+ ion", J. Solid State Electr., 16(10), 3315-3322.   DOI   ScienceOn
23 Hosseini, S.H. and Ghavami, A. (2005), "Chemical and electrochemical synthesis polyvinyl propionate graft polyaniline", Iran. Polym. J., 14(7), 617-626.
24 Arslan, A., Turkarslan, O., Tanyeli, C., Akhmedov, I.M. and Toppare, L. (2007), "Electrochromic properties of a soluble conducting polymer: Poly(1-(4-fluorophenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole)", Mater. Chem. Phys., 104(2-3), 410-416.   DOI
25 Hosseini, S.H. and Entezami, A.A. (2003), "Chemical and electrochemical synthesis of conducting poly diheteroaromatics from pyrrole, indole, carbazole and their mixed containing hydroxamic acid groups and studies of its metal complexes", J. Appl. Polym. Sci., 90(1), 63-71.   DOI   ScienceOn
26 Hosseini, S.H. and Entezami, A.A. (2003), "Chemical and electrochemical synthesis of conducting graft copolymer of vinyl acetate with pyrrole and studies of its gas and vapor sensing", J. Appl. Polym. Sci., 90(1), 40-48.   DOI   ScienceOn
27 Hosseini, S.H. and Mohammadi, M. (2009) "Preparation and characterization of new polypyrrole having side chain liquid crystalline moieties", Mater. Sci. Eng. C, 29(5), 1503-1509.   DOI