A Single Amino Acid Able to Promote High‐Temperature Ring‐Opening Polymerization by Dual Activation

对偶(语法数字) 聚合 戒指(化学) 开环聚合 化学 高分子化学 材料科学 有机化学 聚合物 艺术 文学类
作者
Elena Gabirondo,Katarzyna Świderek,Edurne Marin,Ainhoa Maiz‐Iginitz,Aitor Larrañaga,Vicent Moliner,Agustín Etxeberria,Haritz Sardón
出处
期刊:Advanced Science [Wiley]
标识
DOI:10.1002/advs.202308956
摘要

Abstract Amino acids are indispensable compounds in the body, performing several biological processes that enable proper functioning. In this work, it is demonstrated that a single amino acid, taurine, is also able to promote the ring‐opening polymerization (ROP) of several cyclic monomers under industrially relevant conditions. It is shown that the unique zwitterionic structure of taurine, where the negatively charged sulfonic acid group and the protonated amine group are separated by two methylene groups, not only provides high thermal stability but also leads to a dual activation mechanism, which is corroborated by quantum mechanical calculations. This unique mechanism allows for the synthesis of polylactide of up to 50 kDa in bulk at 180 °C with good end‐group fidelity using a highly abundant catalyst. Furthermore, cytotoxicity tests confirm that PLLA synthesized with taurine is non‐toxic. Moreover, it is demonstrated that the presence of taurine does not have any detrimental effect on the thermal stability of polylactide, and therefore polymers can be used directly without any post‐polymerization purification. It is believed that the demonstration that a simple structure composed of a single amino acid can promote polymerization can bring a paradigm shift in the preparation of polymers.

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