Synthesis and characterization of pyrrole and thiophene functional polystyrenes via "click chemistry"

Kışkan B., GACAL B., ASAN M., GUNAYDIN E. C., Yılmaz İ., YAGCI Y.

POLYMER BULLETIN, vol.67, no.4, pp.609-621, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 4
  • Publication Date: 2011
  • Doi Number: 10.1007/s00289-010-0412-9
  • Journal Name: POLYMER BULLETIN
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.609-621
  • Keywords: Pyrrole, Thiophene, Polystyrene, Click chemistry, 1,3-Dipolar cycloadditions, 1.3-DIPOLARE CYCLOADDITIONEN, RADICAL POLYMERIZATION, CONJUGATED POLYMERS, CONDUCTING POLYMERS, ORGANISCHER AZIDE, BLOCK-COPOLYMERS, GRAFT-COPOLYMERS, BAND-GAP, POLYPYRROLE, ELECTROPOLYMERIZATION
  • Istanbul Technical University Affiliated: Yes

Abstract

Novel side-chain pyrrole or thiophene functional polystyrenes (PS-Py and PS-Th) were synthesized by using "click chemistry'' strategy. First, approximately 40% of chloro groups of poly(styrene-co-chloromethylstyrene) P(S-co-CMS), prepared by nitroxide mediated radical polymerization (NMRP), were converted to azido groups by using NaN(3) in N,N-dimethylformamide. Propargyl pyrrole was prepared by etherification of 4-(1H-pyrrol-1-yl) phenol prepared by Clauson-Kaas reaction using propargylbromide. Propargyl thiophene was synthesized by heterogeneous esterification reaction between 3-thiophenecarboxylic acid and propargylbromide. Finally, azido-functionalized polystyrene was coupled to these propargyl functional heterocyclics with high efficiency by click chemistry. The intermediates at various stages and final polymers were characterized by spectral analysis and cyclic voltammetry.