Boron Effect on Sugar‐Based Organogelators

The reaction of several alkylglucosides with phenyl boronic acid permitted easy access to a series of alkylglucoside phenyl boronate derivatives. This type of compound has structures similar to those of known benzylidene glucoside organogelators except for the presence of a boronate function in plac...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-11, Vol.26 (61), p.13927-13934
Main Authors: Ludwig, Andreas D., Saint‐Jalmes, Arnaud, Mériadec, Cristelle, Artzner, Franck, Tasseau, Olivier, Berrée, Fabienne, Lemiègre, Loïc
Format: Article
Language:English
Subjects:
alkylglucosides
Boron
boronates
Chemical Sciences
Chemistry
Condensed Matter
Drug delivery
Drug delivery systems
Gelation
Gels
glycolipids
Low concentrations
Moisture content
Morphology
Organic chemistry
Organic solvents
organogels
Physics
Rheological properties
Soft Condensed Matter
Water content
water sensitive
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Summary:The reaction of several alkylglucosides with phenyl boronic acid permitted easy access to a series of alkylglucoside phenyl boronate derivatives. This type of compound has structures similar to those of known benzylidene glucoside organogelators except for the presence of a boronate function in place of the acetal one. Low to very low concentrations of these amphiphilic molecules produced gelation of several organic solvents. The rheological properties of the corresponding soft materials characterized them as elastic solids. They were further characterized by SEM to obtain more information on their morphologies and by SAXS to determine the type of self‐assembly involved within the gels. The sensitivity of the boronate function towards hydrolysis was also investigated. We demonstrated that a small amount of water (5 % v/v) was sufficient to disrupt the organogels leading to the original alkylglucoside and phenyl boronic acid; an important difference with the stable benzylidene‐based organogelators. Such water‐sensitive boronated organogelators could be suitable substances for the preparation of smart soft material for topical drug delivery. Dissolving gels: The synthesis of alkyglucoside phenyl boronic esters has provided a series of organogels in several solvents. Similar to benzylidene‐type organogelators, replacement of the acetal group by a boronate function induced singular self‐assembling properties and high sensitivity to water.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202001970