Efficient Exchange in a Bioinspired Dynamic Covalent Polymer Network via a Cyclic Phosphate Triester Intermediate

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

17 Citaten (Scopus)
174 Downloads (Pure)

Samenvatting

Bond exchange via neighboring group-assisted reactions in dynamic covalent networks results in efficient mechanical relaxation. In Nature, the high reactivity of RNA toward nucleophilic substitution is largely attributed to the formation of a cyclic phosphate ester intermediate via neighboring group participation. We took inspiration from RNA to develop a dynamic covalent network based on β-hydroxyl-mediated transesterifications of hydroxyethyl phosphate triesters. A simple one-step synthetic strategy provided a network containing phosphate triesters with a pendant hydroxyethyl group. 31P solid-state NMR demonstrated that a cyclic phosphate triester is an intermediate in transesterification, leading to dissociative network rearrangement. Significant viscous flow at 60-100 °C makes the material suitable for fast processing via extrusion and compression molding.

Originele taal-2Engels
Pagina's (van-tot)7955–7962
Aantal pagina's8
TijdschriftMacromolecules
Volume54
Nummer van het tijdschrift17
DOI's
StatusGepubliceerd - 14 sep. 2021

Bibliografische nota

Funding Information:
This work was funded by the Dutch Research Council (NWO), project no. 731.016.202.

Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society.

Vingerafdruk

Duik in de onderzoeksthema's van 'Efficient Exchange in a Bioinspired Dynamic Covalent Polymer Network via a Cyclic Phosphate Triester Intermediate'. Samen vormen ze een unieke vingerafdruk.

Citeer dit