Sammanfattning
Carbohydrates belong to the most abundant biomolecules on Earth. The high abundance in combination with their low toxicity, high biocompatibility and biodegradability have made carbohydrates candidates of high potential for utilization as renewable feedstock in various fields, among them material technology.
The rich structural diversity and reactivity of carbohydrates offer possibilities, but also challenges. The reactivities of the functional groups of carbohydrates are often similar, and traditional carbohydrate chemistry frequently involves complex, multistep synthesis routes with various protection group protocols. In this thesis, the aim was to modify carbohydrates through more simple procedures, selectively targeting the carbonyl functionality of monosaccharides to create new C-C bonds, and further modifying the obtained polyols through high-yield procedures using mainly water as the solvent.
The first part of the thesis provides an in-depth investigation of the solid-state behavior of allylated D-mannose in commixture with its enantiomer, allylated Lmannose, particularly addressing the conformation of the compounds. Following steps of the thesis include the preparation of amphiphiles from allylated and propargylated D-mannose through classical click chemistry approaches. The developed protocols are subsequently utilized in the preparation of amphiphilic sulfides from allylated monosaccharides and 1-tetradecanethiol. These amphiphilic compounds act as thermotropic liquid crystals, and a thorough study of how the stereochemistry of the parent polyols influences the thermal and mesomorphic behavior of the liquid crystals was conducted. The last part of the thesis adopts a more practical approach, where low molecular weight organogelators are prepared from mannose-derived polyols. These organogelators proved to be phase selective, and due to the unmodified alkene-moiety, these compounds could potentially be attached to various carrier materials to further increase the stability of the formed gels.
The rich structural diversity and reactivity of carbohydrates offer possibilities, but also challenges. The reactivities of the functional groups of carbohydrates are often similar, and traditional carbohydrate chemistry frequently involves complex, multistep synthesis routes with various protection group protocols. In this thesis, the aim was to modify carbohydrates through more simple procedures, selectively targeting the carbonyl functionality of monosaccharides to create new C-C bonds, and further modifying the obtained polyols through high-yield procedures using mainly water as the solvent.
The first part of the thesis provides an in-depth investigation of the solid-state behavior of allylated D-mannose in commixture with its enantiomer, allylated Lmannose, particularly addressing the conformation of the compounds. Following steps of the thesis include the preparation of amphiphiles from allylated and propargylated D-mannose through classical click chemistry approaches. The developed protocols are subsequently utilized in the preparation of amphiphilic sulfides from allylated monosaccharides and 1-tetradecanethiol. These amphiphilic compounds act as thermotropic liquid crystals, and a thorough study of how the stereochemistry of the parent polyols influences the thermal and mesomorphic behavior of the liquid crystals was conducted. The last part of the thesis adopts a more practical approach, where low molecular weight organogelators are prepared from mannose-derived polyols. These organogelators proved to be phase selective, and due to the unmodified alkene-moiety, these compounds could potentially be attached to various carrier materials to further increase the stability of the formed gels.
| Originalspråk | Engelska |
|---|---|
| Handledare |
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| Utgivningsort | Turku |
| Förlag | |
| Tryckta ISBN | 978-952-389-076-3 |
| Elektroniska ISBN | 978-952-389-077-0 |
| Status | Publicerad - 2024 |
| MoE-publikationstyp | G4 Doktorsavhandling (monografi) |