Amphiphilic oligo(2-ethyl-2-oxazoline)s via straightforward synthesis and their self-assembly behaviour. Lefley, J., Varanaraja, Z., Drain, B., Huband, S., Beament, J., & Becer, C. R. POLYMER CHEMISTRY, 14(43):4890–4897, November, 2023. Infineum UK Ltddoi abstract bibtex The synthesis of poly(2-oxazoline)s offers an unparalleled degree of functionalization when fabricating smart, functional polymers for biomedical uses. The termination of 2-oxazoline polymerisations by direct endcapping can be exploited to introduce a wide variety of end groups and could potentially offer an easier synthetic route to amphiphilic polymers that usually block copolymer synthesis. Herein, we report a facile one-pot synthesis and preparation of dodecyl-end capped oligo(2-ethyl-2-oxazoline)s via direct endcapping and thiol-yne click chemistry. A small set of propargyl tosylate initiated PEtOx oligomers were synthesised and subsequently functionalized with varying equivalents of dodecanethiol. GPC, NMR and MALDI-ToF were utilised for molecular weight analysis and determination of end-group fidelity. Film rehydration was employed to prepare self-assembled nanoparticles due the inexpensive set-up and practical simplicity of the technique. DLS, SAXS and TEM revealed that mono- and di-functionalized PEtOx self-assembled into micelles around 10 nm in diameter whereas tri-functionalized PEtOx was too hydrophobic and precipitated in aqueous solution. All oligomers were screened for their ability to encapsulate a model hydrophobic drug, curcumin, and UV-Vis spectrometry was utilized to determine the encapsulation efficiencies and drug loading capacities. Di-functionalized PEtOx provided the greatest drug loading capacity (8 wt%) of this study.
@article{lefley_amphiphilic_2023,
title = {Amphiphilic oligo(2-ethyl-2-oxazoline)s via straightforward synthesis and their self-assembly behaviour},
volume = {14},
issn = {1759-9954},
doi = {10.1039/d3py00809f},
abstract = {The synthesis of poly(2-oxazoline)s offers an unparalleled degree of functionalization when fabricating smart, functional polymers for biomedical uses. The termination of 2-oxazoline polymerisations by direct endcapping can be exploited to introduce a wide variety of end groups and could potentially offer an easier synthetic route to amphiphilic polymers that usually block copolymer synthesis. Herein, we report a facile one-pot synthesis and preparation of dodecyl-end capped oligo(2-ethyl-2-oxazoline)s via direct endcapping and thiol-yne click chemistry. A small set of propargyl tosylate initiated PEtOx oligomers were synthesised and subsequently functionalized with varying equivalents of dodecanethiol. GPC, NMR and MALDI-ToF were utilised for molecular weight analysis and determination of end-group fidelity. Film rehydration was employed to prepare self-assembled nanoparticles due the inexpensive set-up and practical simplicity of the technique. DLS, SAXS and TEM revealed that mono- and di-functionalized PEtOx self-assembled into micelles around 10 nm in diameter whereas tri-functionalized PEtOx was too hydrophobic and precipitated in aqueous solution. All oligomers were screened for their ability to encapsulate a model hydrophobic drug, curcumin, and UV-Vis spectrometry was utilized to determine the encapsulation efficiencies and drug loading capacities. Di-functionalized PEtOx provided the greatest drug loading capacity (8 wt\%) of this study.},
number = {43},
urldate = {2023-10-14},
journal = {POLYMER CHEMISTRY},
author = {Lefley, James and Varanaraja, Zivani and Drain, Ben and Huband, Steven and Beament, James and Becer, C. Remzi},
month = nov,
year = {2023},
note = {Infineum UK Ltd},
pages = {4890--4897},
}
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Herein, we report a facile one-pot synthesis and preparation of dodecyl-end capped oligo(2-ethyl-2-oxazoline)s via direct endcapping and thiol-yne click chemistry. A small set of propargyl tosylate initiated PEtOx oligomers were synthesised and subsequently functionalized with varying equivalents of dodecanethiol. GPC, NMR and MALDI-ToF were utilised for molecular weight analysis and determination of end-group fidelity. Film rehydration was employed to prepare self-assembled nanoparticles due the inexpensive set-up and practical simplicity of the technique. DLS, SAXS and TEM revealed that mono- and di-functionalized PEtOx self-assembled into micelles around 10 nm in diameter whereas tri-functionalized PEtOx was too hydrophobic and precipitated in aqueous solution. All oligomers were screened for their ability to encapsulate a model hydrophobic drug, curcumin, and UV-Vis spectrometry was utilized to determine the encapsulation efficiencies and drug loading capacities. 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