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1. Stimuli-responsive gelators from carbamoyl sugar derivatives and their responses to metal ions and tetrabutylammonium salts

   https://doi.org/10.1039/d0ra07587f  

   Wang, Dan ; Chen, Anji ; Morris, Joedian ; Wang, Guijun ( November 2020 , RSC Advances)

   Carbohydrate-based low molecular weight gelators (LMWGs) are interesting compounds with a variety of applications. In this research, a library of nineteen carbamate derivatives of N -acetyl- d -glucosamine were synthesized and characterized, and several derivatives were found to be effective LMWGs. They formed gels in pump oils as well as mixtures of water with ethanol or water with DMSO. The structures of the carbamoyl chains played an important role in the gelation properties, short chain aliphatic derivatives and phenyl carbamates formed gels in more solvents than certain aromatic and dimeric carbamates. The phenyl carbamate gelator was also selected for the encapsulation of naproxen sodium, and the drug slowly diffused from the gel to the aqueous phase as indicated by UV-vis spectroscopy. In addition, we also found that the p -methoxyl benzyl carbamate derivative showed interesting stimuli-responsive gelation properties in the presence of metal salts and tetrabutylammonium salts. The gels were characterized using optical microscopy, scanning electron microscopy, rheology and other methods. The self-assembling mechanisms of the gelators were studied using 1 H NMR spectroscopy. The preparation, characterization, and molecular assembling properties of these compounds are reported. The results obtained from this study are useful for the design of other LMWGsmore »and the sugar derivatives can be explored for different biological applications. The formation of spontaneous ionic gels can be applicable for a plethora of applications including catalysis and environmental remediation.« less
2. Synthesis and characterization of 3- O -esters of N -acetyl- d -glucosamine derivatives as organogelators

   https://doi.org/10.1039/c9nj00630c  

   Chen, Anji ; Samankumara, Lalith P. ; Garcia, Consuelo ; Bashaw, Kristen ; Wang, Guijun ( May 2019 , New Journal of Chemistry)

   Carbohydrate derived low molecular weight organogelators are interesting compounds with many potential applications. Selective functionalization of the different hydroxyl substituents on d -glucose and d -glucosamine resulted in small molecular gelators. Previously we have found that the C-2 acylated derivatives including esters and carbamates of 4,6- O -benzylidene protected glucose and glucosamine derivatives have shown remarkable applications as molecular gelators. In this research, in order to probe the structural influence of sugar derivatives on molecular self-assembly, we introduced acylation functional groups to the 3-hydroxyl group of 4,6- O -benzylidene acetal protected N -acetyl glucosamine derivatives. A library of fourteen ester derivatives was synthesized and characterized. The ester derivatives typically formed gels in pump oil and aqueous mixtures of dimethyl sulfoxide or ethanol. The resulting gels were characterized using optical microscopy, and rheology, etc. All alkyl ester derivatives were gelators for pump oil. A short chain ester derivative was able to form gels in a few different oils and the corresponding oil water mixtures phase selectively. The compound was also used to trap naproxen sodium and formed a stable co-gel. The controlled release of the drug from the gel to the aqueous phase was analyzed using UV-vis spectroscopy. These results showmore »that the functionalization at the 3-OH position of the N -acetyl glucosamine derivative is a feasible strategy in designing new classes of organogelators.« less
3. Fine-Tuning of Molecular Structures to Generate Carbohydrate Based Super Gelators and Their Applications for Drug Delivery and Dye Absorption

   https://doi.org/10.3390/gels7030134  

   Bietsch, Jonathan ; Olson, Mary ; Wang, Guijun ( September 2021 , Gels)

   Carbohydrate-based low molecular weight gelators (LMWGs) exhibit many desirable properties making them useful in various fields including applications as drug delivery carriers. In order to further understand the structural connection to gelation properties, especially the influence of halide substitutions, we have designed and synthesized a series of para-chlorobenzylidene acetal protected D-glucosamine amide derivatives. Fifteen different amides were synthesized, and their self-assembling properties were assessed in multiple organic solvents, as well as mixtures of organic solvents with water. All derivatives were found to be gelators for at least one solvent and majority formed gels in multiple solvents at concentrations lower than 2 wt%. A few derivatives rendered remarkably stable gels in aqueous solutions at concentrations below 0.1 wt%. The benzamide 13 formed gels in water and in EtOH/H2O (v/v 1:2) at 0.36 mg/mL. The gels were characterized using optical microscopy and atomic force microscopy, and the self-assembly mechanism was probed using variable temperature 1H-NMR spectroscopy. Gel extrusion studies using H2O/DMSO gels successfully printed lines of gels on glass slides, which retained viscoelasticity based on rheology. Gels formed by the benzamide 13 were used for encapsulation and the controlled release of chloramphenicol and naproxen, as well as for dye removal for toluidinemore »blue aqueous solutions.« less
4. 4,6-O-Phenylethylidene Acetal Protected D-Glucosamine Carbamate-Based Gelators and Their Applications for Multi-Component Gels

   https://doi.org/10.3390/gels8030191  

   Sharma, Pooja ; Wang, Guijun ( March 2022 , Gels)

   The self-assembly of carbohydrate-based low molecular weight gelators has led to useful advanced soft materials. The interactions of the gelators with various cations and anions are important in creating novel molecular architectures and expanding the scope of the small molecular gelators. In this study, a series of thirteen new C-2 carbamates of the 4,6-O-phenylethylidene acetal-protected D-glucosamine derivatives has been synthesized and characterized. These compounds are rationally designed from a common sugar template. All carbamates synthesized were found to be efficient gelators and three compounds are also hydrogelators. The resulting gels were characterized using optical microscopy, atomic force microscopy, and rheology. The gelation mechanisms were further elucidated using 1H NMR spectroscopy at different temperatures. The isopropyl carbamate hydrogelator 7 formed hydrogels at 0.2 wt% and also formed gels with several tetra alkyl ammonium salts, and showed effectiveness in the creation of gel electrolytes. The formation of metallogels using earth-abundant metal ions such as copper, nickel, iron, zinc, as well as silver and lead salts was evaluated for a few gelators. Using chemiluminescence spectroscopy, the metal–organic xerogels showed enzyme-like properties and enhanced luminescence for luminol. In addition, we also studied the applications of several gels for drug immobilizations and the gels showedmore »sustained release of naproxen from the gel matrices. This robust sugar carbamate-derived gelator system can be used as the scaffold for the design of other functional materials with various types of applications.« less
5. Synthesis and characterization of pentaerythritol derived glycoconjugates as supramolecular gelators

   https://doi.org/10.1039/c9ob00475k  

   Chen, Anji ; Wang, Dan ; Bietsch, Jonathan ; Wang, Guijun ( June 2019 , Organic & Biomolecular Chemistry)

   Carbohydrate based self-assembling supramolecular systems are important classes of new materials with many potential applications. In this study, a series of twelve glycoconjugates were synthesized and characterized in order to obtain effective supramolecular gelators. These glycoconjugates are mono-, di-, tri-, and tetra-functionalized pentaerythritol derivatives synthesized by using copper( i ) catalyzed azide alkyne cycloaddition reactions (CuAACs). The properties of these twelve compounds gave insight into the rational design of covalently linking multiple units of sugars. We found that the trivalent and tetravalent glycoclusters were effective molecular gelators, but the monovalent and divalent derivatives were typically not able to form gels in the tested solvents. The gels were characterized using rheology, optical microscopy, and atomic force microscopy. The tris-triazole derivative 21 was discovered to be a suitable gelator for the encapsulation of naproxen, vitamin B 2 , and vitamin B 12 . The strategy of covalently linking three or four small molecules to form trimeric or tetrameric branched compounds is a valid approach in designing useful self-assembling materials. The glycocluster based organogels and hydrogels obtained in this study have potential applications in biomedical research and as advanced functional materials.