Cheuk Sherwin, Stevens Edwin D, Wang Guijun
Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA.
Carbohydr Res. 2009 Mar 10;344(4):417-25. doi: 10.1016/j.carres.2008.12.006. Epub 2008 Dec 13.
Low molecular weight gelators are an interesting new type of compounds that are important in supramolecular chemistry and advanced materials. Previously, we had synthesized several acyl derivatives of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and found that a number of terminal acetylene-containing esters are good gelators. To understand the structure requirement of the acyl chains, we synthesized a series of analogs containing different functional groups including aryl, alkenyl, and halogen derivatives. X-ray crystal structures of a monoester and a diester derivative were also obtained to help understand the relationship between structure and gelation. For good gelation properties, the carboxyl derivatives should possess alkyl groups containing a terminal acetylene group and aryl derivatives.
低分子量凝胶剂是一类有趣的新型化合物，在超分子化学和先进材料领域具有重要意义。此前，我们合成了几种4,6-O-亚苄基-α-D-吡喃葡萄糖苷甲酯的酰基衍生物，发现一些含末端乙炔的酯是良好的凝胶剂。为了解酰基链的结构要求，我们合成了一系列含有不同官能团的类似物，包括芳基、烯基和卤素衍生物。还获得了一种单酯和一种二酯衍生物的X射线晶体结构，以帮助理解结构与凝胶化之间的关系。为了具备良好的凝胶化性能，羧基衍生物应具有含末端乙炔基的烷基和芳基衍生物。
