Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone
For about the last ten years, poly(2-oxazoline)s have attracted significant attention as potential material for biomedical applications in, e.g., drug delivery systems, tissue engineering and more. Commonly, the synthesis of poly(2-oxazoline)s involves problematic organic solvents that are not ideal...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.21 |
| _version_ | 1811158675151126528 |
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| author | Solomiia Borova Robert Luxenhofer |
| author_facet | Solomiia Borova Robert Luxenhofer |
| author_sort | Solomiia Borova |
| collection | DOAJ |
| description | For about the last ten years, poly(2-oxazoline)s have attracted significant attention as potential material for biomedical applications in, e.g., drug delivery systems, tissue engineering and more. Commonly, the synthesis of poly(2-oxazoline)s involves problematic organic solvents that are not ideal from a safety and sustainability point of view. In this study, we investigated the cationic ring-opening polymerization of 2-ethyl-2-oxazoline and 2-butyl-2-oxazoline using a variety of initiators in the recently commercialized "green" solvent dihydrolevoglucosenone (DLG). Detailed 1H NMR spectroscopic analysis was performed to understand the influence of the temperature and concentration on the polymerization process. Size exclusion chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry were performed to determine the molar mass of the resulting polymers. Our work shows clearly that the solvent is not inert under the conditions typically used for the cationic ring-opening polymerization, as evidenced by side products and limited control over the polymerization. However, we could establish that the use of the 2-ethyl-3-methyl-2-oxazolinium triflate salt as an initiator at 60 °C results in polymers with a relatively narrow molar mass distribution and a reasonable control over the polymerization process. Further work will be necessary to establish whether a living polymerization can be achieved by additional adjustments. |
| first_indexed | 2024-04-10T05:27:03Z |
| format | Article |
| id | doaj.art-8e1009c49c194444a9b11b1ea70cddf0 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-10T05:27:03Z |
| publishDate | 2023-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-8e1009c49c194444a9b11b1ea70cddf02023-03-07T13:31:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-02-0119121723010.3762/bjoc.19.211860-5397-19-21Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenoneSolomiia Borova0Robert Luxenhofer1Functional Polymer Materials, Chair for Advanced Materials Synthesis, Institute for Functional Materials and Biofabrication, Department of Chemistry and Pharmacy, Julius-Maximilans-University of Würzburg, Röntgenring 11, 97070 Würzburg, Germany Functional Polymer Materials, Chair for Advanced Materials Synthesis, Institute for Functional Materials and Biofabrication, Department of Chemistry and Pharmacy, Julius-Maximilans-University of Würzburg, Röntgenring 11, 97070 Würzburg, Germany For about the last ten years, poly(2-oxazoline)s have attracted significant attention as potential material for biomedical applications in, e.g., drug delivery systems, tissue engineering and more. Commonly, the synthesis of poly(2-oxazoline)s involves problematic organic solvents that are not ideal from a safety and sustainability point of view. In this study, we investigated the cationic ring-opening polymerization of 2-ethyl-2-oxazoline and 2-butyl-2-oxazoline using a variety of initiators in the recently commercialized "green" solvent dihydrolevoglucosenone (DLG). Detailed 1H NMR spectroscopic analysis was performed to understand the influence of the temperature and concentration on the polymerization process. Size exclusion chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry were performed to determine the molar mass of the resulting polymers. Our work shows clearly that the solvent is not inert under the conditions typically used for the cationic ring-opening polymerization, as evidenced by side products and limited control over the polymerization. However, we could establish that the use of the 2-ethyl-3-methyl-2-oxazolinium triflate salt as an initiator at 60 °C results in polymers with a relatively narrow molar mass distribution and a reasonable control over the polymerization process. Further work will be necessary to establish whether a living polymerization can be achieved by additional adjustments.https://doi.org/10.3762/bjoc.19.212-alkyl-2-oxazolinesmatrix-assisted laser desorption/ionization mass spectrometrynuclear magnetic resonancepolymerization kinetics |
| spellingShingle | Solomiia Borova Robert Luxenhofer Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone Beilstein Journal of Organic Chemistry 2-alkyl-2-oxazolines matrix-assisted laser desorption/ionization mass spectrometry nuclear magnetic resonance polymerization kinetics |
| title | Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone |
| title_full | Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone |
| title_fullStr | Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone |
| title_full_unstemmed | Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone |
| title_short | Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone |
| title_sort | investigation of cationic ring opening polymerization of 2 oxazolines in the green solvent dihydrolevoglucosenone |
| topic | 2-alkyl-2-oxazolines matrix-assisted laser desorption/ionization mass spectrometry nuclear magnetic resonance polymerization kinetics |
| url | https://doi.org/10.3762/bjoc.19.21 |
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