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Preparation of Polyaminopyridines Using a CuI/l-Proline-Catalyzed C-N Polycoupling Reaction
National Institute of Metrology, Quality and Technology, DGTEC-INMETRO, 25250-020 Duque de Caxias-RJ, Brazil
Institute of Chemistry, State University of Campinas, UNICAMP, CP 6154, 13083-970 Campinas-SP, Brazil
Institute of Physics, Federal University of Uberlândia, UFU, 38400-902 Uberlândia-MG, Brazil
Department of Chemistry, Institute of Biological and Physical Sciences, Federal University of Ouro Preto, UFOP, 35400-000 Ouro Preto-MG, Brazil
* Author to whom correspondence should be addressed.
Received: 2 August 2012; in revised form: 10 October 2012 / Accepted: 1 November 2012 / Published: 5 November 2012
Abstract: Polyaminopyridines (PAPy) were chemically prepared from amino-bromopyridines by a CuI/l-proline-catalyzed C-N polycondensation reaction. The formation of the polymer was confirmed by GPC, XRD, XRF, FTIR, UV-vis (λmax = 400 nm), 1H and 13C NMR. The number-average molecular weights (Mn) were estimated by end-group analysis using X-ray fluorescence (up to 6000 Da). TGA analysis of PAPy with higher Mn showed greater thermal stability up to 170 oC. Viscosity measurements of polymer in formic acid at 30 oC indicated a polyelectrolyte nature of PAPy solutions. Furthermore, the amorphicity of the material was observed by X-ray diffraction analysis.
Keywords: polyaminopyridines; Ullmann coupling reaction; end-group analysis by XRF
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Reis, L.A.; Ligiéro, C.B.P.; Andrade, A.A.; Taylor, J.G.; Miranda, P.C.M.L. Preparation of Polyaminopyridines Using a CuI/l-Proline-Catalyzed C-N Polycoupling Reaction. Materials 2012, 5, 2176-2189.
Reis LA, Ligiéro CBP, Andrade AA, Taylor JG, Miranda PCML. Preparation of Polyaminopyridines Using a CuI/l-Proline-Catalyzed C-N Polycoupling Reaction. Materials. 2012; 5(11):2176-2189.
Reis, Lindomar A.; Ligiéro, Carolina B.P.; Andrade, Acácio A.; Taylor, Jason G.; Miranda, Paulo C.M.L. 2012. "Preparation of Polyaminopyridines Using a CuI/l-Proline-Catalyzed C-N Polycoupling Reaction." Materials 5, no. 11: 2176-2189.