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光谱法研究羟基葫芦[6]脲与对氨基苯磺酸的分子识别作用

Molecular Recognition Interaction of Perhydroxycucurbit[6]uril with p-Aminobenzenesulfonic Acid by Spectroscopic Methods

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【作者】 李来生葛小辉黄志兵李艳平

【Author】 LI Lai-Sheng~*,GE Xiao-Hui,HUANG Zhi-Bing,LI Yan-Ping (The Center of Analytical and Testing,Nanchang University,Nanchang 330047)

【机构】 南昌大学分析测试中心南昌大学分析测试中心 南昌330047南昌330047

【摘要】 采用紫外和荧光光谱法首次研究羟基葫芦[6]脲(HOCB6)与对氨基苯磺酸(ABS)之间的包结作用,考察了溶液的pH值、常见有机溶剂和表面活性剂等对该包合物的形成及荧光强度的影响。实验结果表明,主客体分子之间通过氢键作用形成1∶1型的HOCB6-ABS外包合物,其包结常数为1.39×103L/mol。同时用葫芦[6]脲(CB6)、β-环糊精和对-二甲氨甲基杯[8]芳烃进行对比。研究发现,ABS与葫芦[6]脲通过疏水作用形成1∶1型的CB6-ABS内包合物,与对-二甲氨甲基杯[8]芳烃通过氢键和π-π等作用形成1∶1型的外包合物,包结常数分别为1.31×102和2.57×104L/mol。而β-环糊精的腔体太大,不能包结ABS分子。有趣的是,由于周围引入羟基,氢键作用导致HOCB6-ABS和CB6-ABS具有不同的包结方式。

【Abstract】 The inclusion interaction of perhydroxycucurbit[6]uril(HOCB6) with p-aminobenzene sulfonic acid(ABS) was studied by UV spectroscopic and fluorimetric methods.Several effect factors,such as the pH values,common organic solvents and surfactants on the fluorescent intensity and the stability of the complex were investigated.The results indicate that the hydrogen-bonding interaction between HOCB6 and ABS contributed to the formation of a 1∶1 type exo-inclusion complex.The complex constant was determined to be 1.39×103 L/mol.The comparative studies of HOCB6 with other supramolecules,such as cucurbit\uril(CB6),β-cyclodextrin and p-(N,N-dimethylaminomethyl)-calix\arene,were also carried out by using ABS as guest probe.The spectral changes showed that the stable endo-inclusion complex was formed between cucurbit\uril and ABS through hydrophobic interaction,and the exo-inclusion complex was formed between p-(N,N-dimethylaminomethyl)-calix\arene and ABS through hydrogen-bonding and π-π interactions mainly.Their complex constants were determined to be 1.31×102 L/mol and 2.57×104 L/mol,respectively.While the interaction between β-cyclodextrin and ABS did not exit,which ascribed to the big cavity of β-cyclodextrin.It is noteworthy that the structure of HOCB6-ABS is different from that of its parent CB6-ABS due to the introduction of peripheral hydroxyl groups and hydrogen-bonding interaction.

【基金】 江西省自然科学基金(9920024);江西省教委基金(JJ2006-07)资助项目
  • 【文献出处】 应用化学 ,Chinese Journal of Applied Chemistry , 编辑部邮箱 ,2006年07期
  • 【分类号】O621.25
  • 【被引频次】16
  • 【下载频次】266
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