Stereochemistry-dependent thermotropic liquid crystalline phases of monosaccharide-based amphiphiles
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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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Date
2023-11-21
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en
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18
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Soft Matter, Volume 19, issue 43, pp. 8360-8377
Abstract
Conformational rigidity controls the bulk self-assembly and liquid crystallinity from amphiphilic block molecules to copolymers. The effects of block stereochemistry on the self-assembly have, however, been less explored. Here, we have investigated amphiphilic block molecules involving eight open-chain monosaccharide-based polyol units possessing different stereochemistries, derived from d-glucose, d-galactose, l-arabinose, d-mannose and l-rhamnose (allylated monosaccharides t-Glc*, e-Glc*, t-Gal*, e-Gal*, t-Ara*, e-Ara*, t-Man*, and t-Rha*), end-functionalized with repulsive tetradecyl alkyl chain blocks to form well-defined amphiphiles with block molecule structures. All compounds studied showed low temperature crystalline phases due to polyol crystallization, and smectic (lamellar) and isotropic phases upon heating in bulk. Hexagonal cylindrical phase was additionally observed for the composition involving t-Man*. Cubic phases were observed for e-Glc*, e-Gal*, e-Ara*, and t-Rha* derived compounds. Therein, the rich array of WAXS-reflections suggested that the crystalline polyol domains are not ultra-confined in spheres as in classic cubic phases but instead show network-like phase continuity, which is rare in bulk liquid crystals. Importantly, the transition temperatures of the self-assemblies were observed to depend strongly on the polyol stereochemistry. The findings underpin that the stereochemistry in carbohydrate-based assemblies involves complexity, which is an important parameter to be considered in material design when developing self-assemblies for different functions.Description
| openaire: EC/H2020/788489/EU//BioELCell Funding Information: The Graduate School of Chemical Engineering, the Parliament Office Commission of the Åland Islands, Walter and Lisi Waal's foundation, the Finnish Foundation for Technology Promotion and the Society of Swedish Literature in Finland are gratefully acknowledged for funding this work. Dr J. Rahkila, Turku Centre for Chemical and Molecular Analytics is acknowledged for HRMS analysis of the allylated sugars and NMR-related support. Dr Ville Liljeström is thanked for assistance with the SWAXS measurements. Dr J. Majoinen and Prof. O. Rojas acknowledge funding from the H2020-ERC-2017-Advanced Grant ‘BioELCell’ (788489). Prof. O. Rojas acknowledges the Canada Excellence Research Chair Program (CERC-2018-00006) and Canada Foundation for Innovation (Project number 38623). Prof. Olli Ikkala acknowledges Academy of Finland CoE LIBER (Project number 346108) and the Flagship FinnCERES. The authors acknowledge facilities and technical support by Nanomicroscopy Center at Aalto University. Publisher Copyright: © 2023 The Royal Society of Chemistry.
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Mattsson, I, Majoinen, J, Lahtinen, M, Sandberg, T, Fogde, A, Saloranta-Simell, T, Rojas, O J, Ikkala, O & Leino, R 2023, ' Stereochemistry-dependent thermotropic liquid crystalline phases of monosaccharide-based amphiphiles ', Soft Matter, vol. 19, no. 43, pp. 8360-8377 . https://doi.org/10.1039/d3sm00939d