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Orthogonal functionalization of alternating polyesters: selective patterning of (AB)n sequences† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc03756j
| Content Provider | Semantic Scholar |
|---|---|
| Author | Chen, Thomas T. Unruangsri, Junjuda Zhu, Yunqing Williams, Charlotte K. |
| Copyright Year | 2019 |
| Abstract | Precision functionalized polyesters, with defined monomer sequences, are prepared using an orthogonal post-polymerization strategy. These polyesters can be synthesized from bio-derived monomers and are targeted to degrade, by hydrolysis processes, to biocompatible diols and diacids; the new structures enabled by this methodology would be very difficult to synthesize by alternative strategies. A series of 9 well-defined highly alternating AB-type copolyesters, containing terminal and internal alkene functionalities, are synthesized in high conversions by the ring-opening copolymerization of epoxides and cyclic anhydrides. Firstly, the polyesters are functionalized by a selective hydroboration-oxidation reaction to exclusively and quantitatively hydroxylate the terminal alkenes, leaving the alternating internal alkenes unreacted. Subsequently, the internal alkenes are quantitatively transformed into carboxylic acid, amine, alkyl and oligo-ether groups, by thiol-ene reactions, to afford AB polyesters with alternating functional substituents. Three polyesters showing alternating hydrophilic/hydrophobic side-chain sequences self-assemble in solution to form nanostructures that are characterized using transmission electron microscopy and dynamic light scattering methods (R h = 100-300 nm). The selective patterning methodology provides facile, efficient and orthogonal functionalization of alternating polyesters with near-quantitative (AB) n repeat sequences. The method is expected to be generalizable to other polymers and provides access to completely new AB alternating structures with the potential to exploit ligand multi-valency and adjacency to enhance properties. |
| Starting Page | 9974 |
| Ending Page | 9980 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c9sc03756j |
| PubMed reference number | 32015813 |
| Journal | Medline |
| Volume Number | 10 |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc03756j?page=search |
| Alternate Webpage(s) | https://doi.org/10.1039/c9sc03756j |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
