Synthetic Nitrogen-containing Polymers and their Application as Copper Supports in Click Chemistry

Authors

  • Hallan Bruno de Matos Angeira Gomes  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil
  • Cristiane Aragao de Souza Bastardis  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil
  • Thays Pontes de Freitas  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil
  • Pedro Ivo Canesso Guimaraes  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil
  • Ayres Guimaraes Dias  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil
  • Jorge Luiz de Oliveira Domingos  Lab. de Química Organica, Instituto de Quimica, Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Rio de Janeiro, Brazil

Keywords:

polyvinylimidazole divinylbenzene; polystyryl pyridine; copper supported; click chemistry

Abstract

Two nitrogen-containing polymers were synthesized and used as support for CuSO4 to evaluate their catalytic activity in 1,3-heterodipolar cycloaddition reactions (1,3-DC) of benzylazide and ethyl propiolate. Polyvinylimidazole (PVI-DVB) was obtained by vinylimidazole polymerization with divinylbenzene and polystyryl pyridine (PSP) was prepared by condensation of lutidine and terephtaldehyde and with collidine as the reticulating agent. The activity was measured by titration with staNdard HCl solution, and PVI-DVB showed 4.6 mEg/g and PSP 0.7 mEg/g polymer. Impregnation with copper was possible by stirring the polymers in aqueous CuSO4 solution. PSP fixed less copper (~0.2 %) than PVI-DVB that fixed thirty times more (6.2 %). The 1,3-DC under microwave irradiation, in the presence of PSP-Cu or PVI-DVB-Cu, gave origin to quantitative yields of the triazoles, and 1,4 regioisomer was the main product. By reusing the copper supported (4X), no changes in yields were observed, only a small decrease in regioselectivity.

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International Journal of Scientific Research in Science and Technology

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Published

2017-04-30

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Volume 3, Issue 3, March-April-2017

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Research Articles

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[1]
Hallan Bruno de Matos Angeira Gomes, Cristiane Aragao de Souza Bastardis, Thays Pontes de Freitas, Pedro Ivo Canesso Guimaraes, Ayres Guimaraes Dias, Jorge Luiz de Oliveira Domingos, " Synthetic Nitrogen-containing Polymers and their Application as Copper Supports in Click Chemistry , International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 3, Issue 3, pp.05-11, March-April-2017.