Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

Autor:	Guijun Wang, Dan Wang, Pooja Sharma, Anji Chen
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Anomer Aqueous solution Metal ions in aqueous solution galactose supramolecular gels Triazole self-assembly General Medicine Combinatorial chemistry organogelators Chemistry chemistry.chemical_compound chemistry Galactosides Moiety fluorescence Self-assembly hydrogelators glucose metallogels triazoles QD1-999 Alkyl
Zdroj:	Chemistry, Vol 3, Iss 68, Pp 935-958 (2021) Chemistry Volume 3 Issue 3 Pages 68-958
ISSN:	2624-8549
Popis:	Carbohydrate-based low-molecular-weight gelators (LMWGs) are useful classes of compounds due to their numerous applications. Among sugar-based LMWGs, certain peracetylated sugar beta-triazole derivatives were found to be effective organogelators and showed interesting self-assembling properties. To further understand the structural influence towards molecular assemblies and obtain new functional materials with interesting properties, we designed and synthesized a library of tetraacetyl beta-1-triazolyl alkyl-D-glucosides and D-galactosides, in which a two or three carbon spacer is inserted between the anomeric position and the triazole moiety. A series of 16 glucose derivatives and 14 galactose derivatives were synthesized and analyzed. The self-assembling properties of these new triazole containing glycoconjugates in different solvents were analyzed. Several glucose derivatives were found to be effective LMWGs, with compound 7a forming gels in a variety of organic solvents as well as in the presence of metal ions in aqueous solutions. The organogels formed by several compounds were characterized using optical microscopy, atomic force microscopy (AFM) and UV-vis spectroscopy, etc. The co-gels formed by compound 7a with the Fmoc derivative 7i showed interesting fluorescence enhancement upon gelation. Several gelators were also characterized using powder X-ray diffraction and FT-IR spectroscopy. The potential applications of these sugar-based gelators for drug delivery and dye removal were also studied.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5fabc994d58b9b890cb3ebdd20adb1ca https://doi.org/10.3390/chemistry3030068 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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