Organo-Catalyzed Cationic Ring-Opening Copolymerization of Cyclic Anhydrides with Oxolanes: Access to Structurally Diverse Polyesters

聚酯纤维 阳离子聚合 高分子化学 化学 共聚物 单体 四氢呋喃 乙醚 缩聚物 催化作用 路易斯酸 戒指(化学) 开环聚合 乙烯基醚 有机化学 聚合物 溶剂
作者
Zhiqiang Ding,Mingqian Wang,Bin Wang,Li Pan,Yue‐Sheng Li
出处
期刊:Macromolecules [American Chemical Society]
被引量:1
标识
DOI:10.1021/acs.macromol.3c01899
摘要

The cyclic ether candidates for ring-opening copolymerization (ROCOP) are mainly three-membered oxiranes with high ring tension, while ROCOP of cyclic anhydrides with low ring strain oxolanes was seldom thoroughly investigated. Herein, we report rapid cationic copolymerizations of tetrahydrofuran (THF) with anhydrides to facilely synthesize alternating polyesters. These processes are realized by a highly active organic Lewis acid trityl tetrakis(pentafluorophenyl)borate ([Ph3C]+[B(C6F5)4]−) that is almost inactive for THF homopolymerization. Poly(ester-co-ether)s with AB, ABB, and ABBB-type repeating units (A = anhydride, B = THF) are formed during copolymerization. The alternating enchainment of anhydride and THF can produce AB-type units, while the coupling reactions between trityl ether and oxonium chain ends will generate ABB- and ABBB- type units. The model reactions suggests that AB-, ABB-, and ABBB-type repeating units are interconvertible, and their relative content is determined by reaction time, temperature, and monomer feed ratio. Alternating polyesters are finally formed by feeding equimolar THF and cyclic anhydride. [Ph3C]+[B(C6F5)4]−-catalyzed ROCOP is further extended to other biomass-derived oxolanes and 14 commercially available cyclic anhydrides, thus allowing for the fabrication of polyesters with structural and functional diversity. This methodology provides an alternative approach to some "AB"-type alternating polyesters that are usually obtained by traditional step-growth polycondensation.
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