Molecular Recognition and Sensing of Organophosphorus Compounds and Paraquat by endo-Functionalized Macrocyclic Receptors

Pesticides, including organophosphorus compounds and paraquat, are water-soluble toxic chemicals that can prevent, destroy or control pests. The abuse of pesticides can cause many problems such as threats to humans and endangered species, therefore their detection and detoxification are in urgent need. Traditional instrumental methods such as GC-MS and electrochemical methods for the detection of organophosphorus compounds and paraquat have been developed but cannot detect pesticides with enough efficiency and selectivity, and not convenient because the instruments are often not portable. The use of a complementary host is a good approach in the detection of pesticides. However, the recognition of pesticides in water by synthetic hosts is a great challenge since water provides high desolvation penalty for both the host and the guest upon binding. Therefore, endo-functionalized synthetic hosts, which contain inward-directed polar binding sites that are deeply embedded and protected from the polar environment inside their hydrophobic cavity, were developed to overcome the challenge. In this thesis, the recognition of organophosphorus compounds and paraquat by endo-functionalized naphthotube and naphthobox is described.

农药，包括有机磷化合物和百草枯，是一种水溶性有毒化学品，可以预防、消灭或控制害虫。农药的滥用会给人类和濒危物种带来威胁等诸多问题，因此迫切需要对其进行检测和解毒。已经开发的用于检测有机磷化合物和百草枯的传统仪器方法，例如 GC-MS 和电化学方法，无法以足够的效率和选择性检测农药。另外并且由于仪器通常不便于携带，因此这些检测方法并不方便高效。使用与客体分子互补的大环主体分子来实现识别是检测农药的一种可行方法。然而，合成主体大环对水中农药的识别是一个巨大的挑战，因为水在结合时对主体和客体都提供了很高的去溶剂化惩罚。因此，我们开发了内修饰主体大环以克服这一挑战，该主体大环拥有嵌入空腔内部的极性键合位点，这个设计能使键合位点免受空腔外极性环境影响。本论文描述了使用内修饰萘管大环以及萘盒大环对有机磷化合物和百草枯的识别。