噻唑类有机小分子凝胶剂的合成及其凝胶行为研究

Synthesis and Gelation Behavior of a Novel Bithiazole Based Low-Molecular-Mass Organic Gelator

用2,2’-二氨基-4,4’-联噻唑和胆固醇甲酰氯进行缩合反应,制备出一种新的侧链为胆固醇甲酰胺基的噻唑类有机小分子凝胶因子。该化合物的结构由红外光谱(FT-IR)、核磁氢谱(1H-NMR)、高分辨飞行质谱(MALDI-TOFHRMS)得以确证。为了考察此小分子凝胶因子的自组装行为,研究了该分子在不同有机溶剂中的成胶性能和形貌。研究发现,在一些有机溶剂中该凝胶分子能自组装成片状的结构,其中在苯或甲苯中凝胶性能好,其最小成胶浓度(CGC)为7mg·mL-1。场发射扫描电镜(FE-SEM)照片显示,从甲苯或氯仿溶剂中得到的干胶呈片状结构。通过红外光谱和紫外-可见吸收光谱研究证实,该化合物分子间的氢键和联噻唑基团之间的π-π相互作用是凝胶化的重要驱动力。

A novel bithiazole based low-molecular-mass organic gelator was synthesized from 2,2＇-diamino-bithiazole through condensation reaction with cholesteryl chloroformate.The structure and purity of the prepared organogelator product were identified by the infrared spectra （FT-IR）,the nuclear magnetic resonance spectra for hydrogen （1H-NMR）,and the time-of-flight mass spectrometry （MALDI-TOF HRMS）.The assembly behavior of the prepared organogelator in solution was investigated.The organogelator induces gelation of a wide variety of organic solvents,especially for aromatic solvents.The critical gelation concentration （CGC） of the prepared gelator in toluene is 7 mg·mL-1.The field emission scanning eletron microscope （FE-SEM） images exhibit that the xerogels from toluene and CHCl3 solution contain sheet structure.The curly sheet structures in the xerogel from toluene solution demonstrate that the prepared organogelator has good gelation properties in toluene.The infrared spectra （FT-IR） and UV-vis absorption spectra show that the hydrogen bonding between amide group and the π-π stacking interaction between bithiazoles are the main driving forces for the formation of organogels.