Synthesis and characterization of poly(epsilon-caprolactone) tetra-arm star polymer using tetra terminal alkynyl-substituted phthalocyanine by the combination of ring-opening polymerization and "click" chemistry


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Sava B., Meyvaci E., ÖZTÜRK T., Agirta M. S.

OVIDIUS UNIVERSITY ANNALS OF CHEMISTRY, vol.33, no.1, pp.17-21, 2022 (Peer-Reviewed Journal) identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 1
  • Publication Date: 2022
  • Doi Number: 10.2478/auoc-2022-0003
  • Journal Name: OVIDIUS UNIVERSITY ANNALS OF CHEMISTRY
  • Journal Indexes: Emerging Sources Citation Index
  • Page Numbers: pp.17-21
  • Keywords: tetra-arm star polymer, "click" chemistry, ring-opening polymerization, phthalonitrile derivative, metallophthalocyanine, BLOCK-COPOLYMERS, POWERFUL TOOL

Abstract

The synthesis of poly(epsilon-caprolactone) (PCL) tetra-arm star polymer was carried out using "click" chemistry and ring-opening polymerization techniques. For this purpose, poly(epsilon-caprolactone) azido (PCL-N-3) was acquired using ring-opening polymerization of epsilon-caprolactone and 2-[2-(2-azidoethoxy)ethoxy]ethanol (N(3)ol). N(3)ol was obtained using sodium azide and 2-[2-(2-chloroethoxy)ethoxy]ethanol. 4-(prop-2-ynyloxy)-phthalonitrile was obtained by using 4-nitrophthalonitrile and propargyl alcohol. 2(3),9(10),16(17),23(24) Tetrakis-[(prop-2-ynyloxy)-phthalocyaninato]zinc(II) (Pc-propargyl) was synthesized by using 4-(prop-2-ynyloxy)-phthalonitrile and a metal salt. By reacting Pc-propargyl and PCL-N-3, PCL tetra-arm star polymer was obtained by "click" chemistry. The products were characterized via scanning electron microscopy, H-1-nuclear magnetic resonance spectroscopy, ultraviolet-visible spectrophotometry, Fourier-transform infrared spectroscopy, and gel permeation chromatography instruments. The spectroscopic analyses of PCL tetra-arm star polymer prove that the star polymer was built through the combination of ROP and "click" chemistry. We provided a protocol for PCL tetra-arm star polymer, and a statement of reproducibility with respect to the properties of this tetra-arm star polymer. This study is an example of a novel type of combination reaction, from ring-opening polymerization to "click" chemistry using phthalocyanine. This can open the door for diverse tetra-arm star polymer synthesis that could potentially cause major advances in synthetic macromolecular chemistry.