A Single Amino Acid Able to Promote High-Temperature Ring-Opening Polymerization by Dual Activation
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Other documents of the author: Gabirondo, Elena; Świderek, Katarzyna; Marin, Edurne; Maiz Iginitz, Ainhoa; Larranaga, Aitor; Moliner, Vicent; Etxeberria, Agustin; Sardon, Haritz
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comunitat-uji-handle2:10234/160292
comunitat-uji-handle3:10234/160293
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Title
A Single Amino Acid Able to Promote High-Temperature Ring-Opening Polymerization by Dual ActivationAuthor (s)
Date
2024-04-24Publisher
WileyISSN
2198-3844Bibliographic citation
E. Gabirondo, K. Świderek, E. Marin, A. Maiz-Iginitz, A. Larranaga, V. Moliner, A. Etxeberria, H. Sardon, A Single Amino Acid Able to Promote High-Temperature Ring-Opening Polymerization by Dual Activation. Adv. Sci. 2024, 11, 2308956. https://doi.org/10.1002/advs.202308956Type
info:eu-repo/semantics/articlePublisher version
https://onlinelibrary.wiley.com/doi/full/10.1002/advs.202308956Version
info:eu-repo/semantics/publishedVersionSubject
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 ... [+]
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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Advanced Science, 2024, vol.11, no 16Rights
info:eu-repo/semantics/openAccess
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Except where otherwise noted, this item's license is described as © 2024 The Authors. Advanced Science published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.