Synthesis and characterization of poly(ε-caprolactone) tetra-arm star polymer using tetra terminal alkynyl-substituted phthalocyanine by the combination of ring-opening polymerization and “click” chemistry
{"title":"Synthesis and characterization of poly(ε-caprolactone) tetra-arm star polymer using tetra terminal alkynyl-substituted phthalocyanine by the combination of ring-opening polymerization and “click” chemistry","authors":"B. Savaş, E. Meyvacı, T. Öztürk, M. Ağırtaş","doi":"10.2478/auoc-2022-0003","DOIUrl":null,"url":null,"abstract":"Abstract The synthesis of poly(ε-caprolactone) (PCL) tetra-arm star polymer was carried out using “click” chemistry and ring-opening polymerization techniques. For this purpose, poly(ε-caprolactone) azido (PCL-N3) was acquired using ring-opening polymerization of ε-caprolactone and 2-[2-(2-azidoethoxy)ethoxy]ethanol (N3ol). N3ol 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-N3, PCL tetra-arm star polymer was obtained by “click” chemistry. The products were characterized via scanning electron microscopy, 1H-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.","PeriodicalId":19641,"journal":{"name":"Ovidius University Annals of Chemistry","volume":"8 1","pages":"17 - 22"},"PeriodicalIF":1.0000,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Ovidius University Annals of Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2478/auoc-2022-0003","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 3
Abstract
Abstract The synthesis of poly(ε-caprolactone) (PCL) tetra-arm star polymer was carried out using “click” chemistry and ring-opening polymerization techniques. For this purpose, poly(ε-caprolactone) azido (PCL-N3) was acquired using ring-opening polymerization of ε-caprolactone and 2-[2-(2-azidoethoxy)ethoxy]ethanol (N3ol). N3ol 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-N3, PCL tetra-arm star polymer was obtained by “click” chemistry. The products were characterized via scanning electron microscopy, 1H-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.