Cargando…
A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yiel...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123656/ https://www.ncbi.nlm.nih.gov/pubmed/33926044 http://dx.doi.org/10.3390/polym13091403 |
_version_ | 1783692970646568960 |
---|---|
author | Yan, Jie Marina, Paula Facal Blencowe, Anton |
author_facet | Yan, Jie Marina, Paula Facal Blencowe, Anton |
author_sort | Yan, Jie |
collection | PubMed |
description | Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents. |
format | Online Article Text |
id | pubmed-8123656 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-81236562021-05-16 A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines Yan, Jie Marina, Paula Facal Blencowe, Anton Polymers (Basel) Communication Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents. MDPI 2021-04-26 /pmc/articles/PMC8123656/ /pubmed/33926044 http://dx.doi.org/10.3390/polym13091403 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Yan, Jie Marina, Paula Facal Blencowe, Anton A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title | A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title_full | A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title_fullStr | A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title_full_unstemmed | A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title_short | A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines |
title_sort | facile strategy for the high yielding, quantitative conversion of polyglycol end-groups to amines |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123656/ https://www.ncbi.nlm.nih.gov/pubmed/33926044 http://dx.doi.org/10.3390/polym13091403 |
work_keys_str_mv | AT yanjie afacilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines AT marinapaulafacal afacilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines AT blencoweanton afacilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines AT yanjie facilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines AT marinapaulafacal facilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines AT blencoweanton facilestrategyforthehighyieldingquantitativeconversionofpolyglycolendgroupstoamines |