Design and estimation of fluorescent chiral sensor : from uni-molecular system to organized approach

荧光手性传感器的设计和评估：从单分子系统到组织方法

基本信息

批准号：
13650911
负责人：
KUBO Yuji
金额：
$ 2.62万
依托单位：
Saitama University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2001
资助国家：
日本
起止时间：
2001 至 2002
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-13650911/
关键词：
fluorescent sensor isothiouronium group anion recognition organized molecular layer chirality chilality memory porphyrin crown ether アニオンセンシング 1,1'-ビナフタレン

项目摘要

Synthesis of optical sensors being capable of recognizing and reading out the shape of analyte precisely is one of scientific challenge in the area of molecular recognition chemistry. Most notably, chiral sensing would be desirable not only in analytical chemistry but also in pharmacology. In this project, our strategy to develop elaborated sensing systems is based on the anion recognition. A family of isothiuronium salts, which are known as synthetic intermediates for the conversion of alkyl halides to the corresponding thiols, has potential as one of key functional groups toward this end. Indeed, a sophisticated combination of the functional entity and suitable fluorophore could allow production of a new type of chemosensors via regulation of the efficiency of the photoinduced electron transfer process. In 2002, we tried to develop an isothiouronium derived uni-molecular system for chiral recognition as well as an organized molecular layer. In the latter case, by use of newly synthesized amphiphilic isothiouronium compounds, we successfully prepared the corresponding organized molecular films. Now the detailed molecular recognition phenomena at air-water interface are under investigation.Alternative approach is to develop a novel achiral-to-chiral transformation at the molecular level using "dynamic" host-guest interaction. In this context, chirality-transfer control has been successfully achieved using a 2,2'-biphenyl- 20-crown-6-bridged bis(zinc(II) porphysic). Further, chirality-induction in a large-sized crown ether with a highly conformational flexibility was obtained through K^+ and I coordinated self-assembly in the solid state. Taken together, I believe that these findings would open new way to "dynamic" chiral recognition.

能够识别和读取分析物的形状的光传感器的合成是分子识别化学领域的科学挑战之一。最值得注意的是，手性传感不仅在分析化学中，而且在药理学方面都是可取的。在这个项目中，我们开发详细传感系统的策略是基于阴离子识别的。异硫硫龙盐家族，被称为合成中间体，用于将烷基卤化物转化为相应的硫醇，它是对此末端的关键官能团之一的潜力。实际上，功能实体和合适的荧光团的复杂组合可以通过调节光诱导的电子传递过程的效率来产生新型的化学传感器。在2002年，我们试图开发一种用于手性识别和有组织的分子层的异硫龙衍生的单分子系统。在后一种情况下，通过使用新合成的Amphielic isothiouronium化合物，我们成功地准备了相应的有组织的分子膜。现在，正在研究空气 - 水界面的详细分子识别现象。替代方法是使用“动态”宿主 - 宿主相互作用在分子水平上开发一种新型的精神分裂 - 手续转化。在这种情况下，使用2,2'-二苯基-20克（锌（II）斑岩）成功实现了手性转移控制。此外，通过K^+获得了具有高构象柔韧性的大型冠状以太的手性诱导，并在固态下协调自组装。综上所述，我相信这些发现将开辟“动态”手性识别的新方法。