均苯四甲酸酯衍生物小分子凝胶剂的合成研究

Synthesis of Homophthallic Acid Ester Derivatives as Low Molecular Weight Gelator

设计合成了一种新型的以π⁃π堆积为主导作用力的凝胶因子,通过生成均苯四甲酸酯的形式来减少氢键作用位点,以均苯四甲酸二酐为母核结构与不同碳链长度的醇反应,成功合成了一系列不同碳链长度的均苯四甲酸酯的凝胶因子衍生物,进而探讨了这些凝胶因子衍生物在常见的不同有机溶剂中形成凝胶的性能。流变学测试显示,该凝胶体系的弹性模量比储能模量高一个数量级,有很好的机械性能,并且呈现出典型的类固体的流变学行为。傅里叶红外光谱、核磁共振谱、扫描电镜及DSC结果表明,凝胶中凝胶剂分子形成纤维状的自组装聚集体,以均苯四甲酸二酐为母核结构的凝胶剂分子中π⁃π堆积的弱相互作用力以及分子间的范德华力是形成该凝胶的主要驱动力,形成的聚集体相互缠绕,最终形成三维网络结构阻碍溶剂流动从而形成凝胶。

A new type of gelator withπ⁃πstacking as weak interaction force was designed and synthesized.Pyromellitic acid esters were synthesized from pyromellitic dianhydride and alcohols of different carbon chain lengths to reduce hydrogen bonding sites.Then the gel capabilities were explored in common different organic solvents.The rheological test shows that the elastic modulus of the gel system is ten folds higher than the storage modulus,indicating that the gel has good mechanical properties and exhibits typical solid⁃like rheological behavior.Fourier transform infrared spectroscopy,nuclear magnetic resonance spectroscopy,scanning electron microscopy and DSC results show gelators formed fibrous self⁃assembled aggregates in gel under driving force fromπ⁃πstacking and the van der Waals force.The formed aggregates entangle with each other and finally form a three⁃dimensional network structure that hinders the flow of the solvent to form the gel.