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

IF 1 Q4 CHEMISTRY, MULTIDISCIPLINARY
B. Savaş, E. Meyvacı, T. Öztürk, M. Ağırtaş
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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.
用开环聚合和“咔嗒”化学相结合的方法合成四端炔基取代酞菁聚ε-己内酯四臂星形聚合物
摘要采用“咔嗒”化学和开环聚合技术合成了聚ε-己内酯(PCL)四臂星形聚合物。为此,用ε-己内酯和2-[2-(2-叠氮乙氧基)乙氧基]乙醇(N3ol)开环聚合法制备聚(ε-己内酯)叠氮基(PCL-N3)。用叠氮化钠和2-[2-(2-氯乙氧基)乙氧基]乙醇制备N3ol。以4-硝基邻苯二腈和丙炔醇为原料制备了4-(丙-2-乙氧基)邻苯二腈。以4-邻苯二腈和金属盐为原料合成了2(3)、9(10)、16(17)、23(24)-[(丙基-2-酰氧基)-酞菁酸]锌(II) (pc -丙炔基)。PCL-丙炔与PCL- n3反应,通过“咔嗒”化学得到PCL四臂星形聚合物。通过扫描电镜、核磁共振、紫外可见分光光度、傅里叶变换红外光谱、凝胶渗透色谱等仪器对产物进行了表征。对PCL四臂星形聚合物的光谱分析证明,星形聚合物是通过机械钻速和“咔嗒”化学相结合构建的。我们提供了PCL四臂星形聚合物的协议,以及关于该四臂星形聚合物性质的可重复性声明。这项研究是一种新型组合反应的一个例子,从开环聚合到使用酞菁的“点击”化学。这可以为多种四臂星形聚合物的合成打开大门,可能会在合成大分子化学方面取得重大进展。
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来源期刊
Ovidius University Annals of Chemistry
Ovidius University Annals of Chemistry CHEMISTRY, MULTIDISCIPLINARY-
自引率
11.10%
发文量
20
审稿时长
5 weeks
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