6–全脱氧–6–全氯代–β–环糊精的合成及自组装行为

Self-assembly Behavior and Synthesis of Per(6-chlorin-6-deoxy)-β-cyclodextrin

为了获得需要的结构分子,利用β–环糊精、咪唑和苯磺酰氯反应合成了6–全脱氧–6–全氯代–β–环糊精.通过X射线衍射分析、核磁光谱及热重分析等方法进行了表征.晶体结构显示,化合物分子利用β–环糊精小口端的头–对–头相互作用以及大口端的尾–对–尾相互作用沿着a轴进行排列,形成线状超结构,其中在小口端通过Cl—Cl相互作用和氢键作用形成了疏水层,而在大口端通过羟基之间的氢键形成了亲水层.热重分析结果表明β–环糊精分子间相互作用的减弱导致化合物不同的热力学特性.

In order to obtain the molecule with a needed structure,the modified β-cyclodextrin,per(6-chlorin-6-deoxy)-β-cyclodextrin,was synthesized through the reaction of β-cyclodextrin,benzenesulfonyl chloride and imidazole in N,Ndimethylformamide(DMF).Its molecular structure was measured by X-ray crystallography,1H NMR spectroscopy,and thermogravimetric analysis(TGA).The crystal structure shows that the molecules of the compound are aligned on the a-axis to form a linear superstructure through head-to-head interactions at the primary side and tail-to-tail interactions at the secondary side.At the primary side,the chlorine atoms,through Cl—Cl interaction and that of hydrogen bonds,form hydrophobic layers,and at the secondary,the hydroxyl groups interact through hydrogen bonds to form hydrophilic layers.Thermogravimetric analysis shows that the different thermodynamic character results from the weakening of the interaction between the adjacent β-cyclodextrins.