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

Authors :
Elena Gabirondo
Katarzyna Świderek
Edurne Marin
Ainhoa Maiz‐Iginitz
Aitor Larranaga
Vicent Moliner
Agustin Etxeberria
Haritz Sardon
Source :
Advanced Science, Vol 11, Iss 16, Pp n/a-n/a (2024)
Publication Year :
2024
Publisher :
Wiley, 2024.

Abstract

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.

Details

Language :
English
ISSN :
21983844
Volume :
11
Issue :
16
Database :
Directory of Open Access Journals
Journal :
Advanced Science
Publication Type :
Academic Journal
Accession number :
edsdoj.1b6f133c258547ee8de30319225e5453
Document Type :
article
Full Text :
https://doi.org/10.1002/advs.202308956