Synthesis and characterization of pentaerythritol derived glycoconjugates as supramolecular gelators
Synthesis and characterization of pentaerythritol derived glycoconjugates as supramolecular gelators
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DOI：
10.1039/c9ob00475k
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发表时间：
2019-06-28
影响因子：
3.2
通讯作者：
Wang, Guijun
中科院分区：
文献类型：
--
作者：
Chen, Anji;Wang, Dan;Wang, Guijun
糖基自组装超分子体系是一类重要的新型材料，具有广泛的应用前景。为了获得高效的超分子凝胶因子，本研究合成了一系列十二种糖缀合物并对其进行了表征。这些糖缀合物是通过使用铜（i）催化的叠氮化物炔环加成反应（CuAAC）合成的单官能化、二官能化、三官能化和四官能化的季戊四醇衍生物。这12种化合物的性质使我们深入了解了共价连接多个糖单元的合理设计。我们发现，三价和四价糖簇是有效的分子胶凝剂，但单价和二价衍生物通常不能在测试的溶剂中形成凝胶。使用流变学，光学显微镜和原子力显微镜的凝胶进行了表征。发现三-三唑衍生物21是用于包封萘普生、维生素B-2和维生素B-12的合适胶凝剂。将三个或四个小分子共价连接形成三聚或四聚支化化合物的策略是设计有用的自组装材料的有效方法。本研究中得到的糖簇基有机凝胶和水凝胶在生物医学研究和作为先进功能材料方面具有潜在的应用。
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.