Al-Shok, Lucas, Town, James S., Coursari, Despina, Wilson, Paul and Haddleton, David M. (2023) Post-polymerisation modification of poly(3-hydroxybutyrate) (PHB) using thiol–ene and phosphine addition. Polymer Chemistry, 14 (22). pp. 2734-2741. doi:10.1039/d3py00272a ISSN 1759-9962.
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Abstract
As we face the issues associated with fossil resource-based polymers and their environmental impact after their useful life, polyesters become more important as “greener” alternatives due to their potential hydrolytic and enzymatic degradability in various environments. Moreover, post-modifying their structure can additionally open up access to a variety of new materials. During this work the potential to post-modifying synthetic PHB made via the organocatalysed ring-opening polymerisation of β-butyrolactone (β-BL) is shown. Modification by thiol–ene ‘click’ chemistry was succesfully conducted under UV-initiation. Surprisingly, attempting the modification under thermal conditions using dimethylphenylphosphine (DMPP) as catalyst, resulted in the attachment of the phosphine, as shown via NMR spectroscopy. Control experiments using crotonic acid, methyl crotonate and n-butyric acid indicated that the presence of a carboxylic acid group is necessary in order for the phosphine addition to occur. Further, the formation of particles shown via dynamic light scattering (DLS), zeta-potential (ZP) and transmission electron microscopy (TEM) measurements suggest an amphiphilic character of the phosphine-functionalised polymers. Finally, stability studies in the presence of salt and different pH environments revealed a high responsiveness and dependency between pH and particle size as well as surface charge.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry |
| SWORD Depositor: | Library Publications Router |
| Library of Congress Subject Headings (LCSH): | Polymerization, Thiols -- Research, Phosphine |
| Journal or Publication Title: | Polymer Chemistry |
| Publisher: | The Royal Society of Chemistry |
| ISSN: | 1759-9962 |
| Official Date: | 14 June 2023 |
| Dates: | Date Event 14 June 2023 Published 5 May 2023 Available 4 May 2023 Accepted |
| Volume: | 14 |
| Number: | 22 |
| Page Range: | pp. 2734-2741 |
| DOI: | 10.1039/d3py00272a |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Open Access (Creative Commons open licence) |
| Date of first compliant deposit: | 9 June 2023 |
| Date of first compliant Open Access: | 9 June 2023 |
| RIOXX Funder/Project Grant: | Project/Grant ID RIOXX Funder Name Funder ID EP/V036211/1 [EPSRC] Engineering and Physical Sciences Research Council EP/V007688/1 [EPSRC] Engineering and Physical Sciences Research Council |
| Related URLs: | |
| URI: | https://wrap.warwick.ac.uk/175774/ |
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