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Preparation of Box-shaped Cyclophane Compounds Recognizing Endocrine Disruptors and their Immobilization

识别内分泌干扰物的盒状环芳化合物的制备及其固定化

基本信息

批准号：
11650900
负责人：
TSUGE Akihiko
金额：
$ 2.05万
依托单位：
Kyushu Institute of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1999
资助国家：
日本
起止时间：
1999 至 2000
项目状态：
已结题

项目摘要

Complexation of macrocyclic cyclophane compounds with guest molecules in water has always attracted a major interest since it can mimic the molecular recognition which is a basic process in biological systems. Although modified cyclodextrins have been extensively investigated in terms of inclusion, recognition, and catalysis in aqueous media, versatility of their structure is limited. On the contrary water-soluble calixarenes and cyclophanes have a great advantage of molecular design. On the other hand it has been reported that the chemical compounds known as endocrine disrupters could have an unexpected influence on human beings. Thus, novel cyclophans consisting of fluorene, naphthalene, anthracene or pyrene component which could exhibit a binding ability against some kinds of endocrine disrupters have been proposed. We have shown the facile synthetic methods of such macrocyclic cyclophanes containing fluorene, naphthalene, anthracene or pyrene component. In order to recognize the en … More docrine disrupters weak intermolecular interactions such as CH-π interaction, π-π interaction, hydrogen bondings and so on could be very important. We have clarified the conformational properties of these cyclophanes, indicating that the ring inversion is highly dependent on their molecular structures, especially the inner substituents and the length of the bridging part. Hydrogen bondings also play a decisive role on the conformation. Some cyclophanes exhibit a very interesting properties by switching an intramolecular hydrogen bonding to an intermolecular one. During this process crystal structure changes. In the cyclophanes having the fluorene component fluorescence energy transfer is observed, depending the rigidity of the molecule and the orientation of two aromatic components. The cyclophanes consisting of anthracene or pyrene unit exhibit a unique CH-π interaction between the amino group and the aromatic unit, which has an influence on the conformation. Now we are developing the desired system using the knowledge of weak interactions obtained here. Less

大环环芳类化合物与客体分子在水中的络合反应一直受到人们的关注，因为它可以模拟生物体系中的基本分子识别过程。虽然改性环糊精在水介质中的包合、识别和催化作用方面已经得到了广泛的研究，但其结构的通用性有限。而水溶性杯芳烃和环番化合物在分子设计上具有很大的优势。另一方面，据报道，被称为内分泌干扰物的化合物可能对人类产生意想不到的影响。因此，由芴、萘、蒽或芘组成的新型环番化合物可以表现出对某些内分泌干扰物的结合能力。本文介绍了含芴、萘、蒽、芘等大环化合物的简便合成方法。为了识别EN ...更多信息弱的分子间相互作用如CH-π相互作用、π-π相互作用、氢键等可能是非常重要的。我们已经澄清了这些环番的构象特性，表明环反转是高度依赖于它们的分子结构，特别是内部取代基和桥接部分的长度。氢键对构象也起着决定性的作用。一些环番化合物通过将分子内氢键转换为分子间氢键而表现出非常有趣的性质。在这个过程中，晶体结构发生了变化。在具有芴组分的环番中观察到荧光能量转移，这取决于分子的刚性和两个芳族组分的取向。由蒽或芘结构单元组成的环番化合物的氨基与芳香单元之间存在独特的CH-π相互作用，从而影响其构象。现在，我们正在利用这里获得的弱相互作用知识开发所需的系统。少