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

大环环烷化合物与水中客体分子的络合一直引起人们的广泛兴趣，因为它可以模拟生物系统中的基本过程分子识别，尽管改性环糊精在水体中的包合、识别和催化方面已得到广泛研究。相反，水溶性杯芳烃和环芳烃在分子设计方面具有很大优势。另一方面，据报道，被称为内分泌干扰物的化合物可以。因此，我们已经提出了由芴、萘、蒽或芘成分组成的新型环芳烷，其可以表现出对某些种类的内分泌干扰物的结合能力。芴、萘、蒽或芘成分为了识别弱分子间相互作用，例如CH-π相互作用， π-π相互作用、氢键等可能非常重要，我们已经阐明了这些环烷的构象性质，表明环反转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。在此过程中，氢键通过将分子内氢键转变为分子间氢键，对构象也起着决定性作用。观察到具有芴组分的环烷的荧光能量转移，这取决于分子的刚性和两个芳香族组分的取向。由蒽或芘单元组成的环烷在氨基和芳香族单元之间表现出独特的CH-π相互作用，现在我们正在利用这里获得的弱相互作用的知识来开发所需的系统。