Design And Synthesis Of Fluorescently-labeled Persistent Organic Pollutants

Persistent organic pollutants (POPs) refer to chemical substances that possess the characteristics of high toxicity, long half-life, the ability to bioaccumulate through foodwebs and transport over long distances via various environmental media such as air, water, organisms and so on. The existence of these compounds poses great adverse effects to human health and ecosystem. Pentachlorophenol (PCP), octachlorostyrene (OCS) and tris(2,3-dibromopropyl) isocyanurate (TBC) have become POPs canadidatates due to their POPs nature. Compared with conventional physicochemical analytical techniques for detection, fluoroimmunoassays (FIAs) offer a number of advantages. FIAs can provide a fast, simple and cost-effective method of detection, with mirco sample volume needed, and sensitivity and specificity comparable to or even better than the conventional methods. More important, on-site analysis of numerous samples is possible with immunoassays. Thus, for the purpose of developing FIAs for detection of these three toxic substances, this work was carried out as follows:Firstly, in order to choose fluorescence markers with good properties and investigate the impacts on characteristics of antibodies, three haptens for PCP were synthetized, which were labeled by coumarin, naphthalic anhydride and8-hydroxyquinoline derivative respectively, via Williamson etherification reaction, Sonogashira coupling reaction and some other reactions.Secondly, one OCS analogue with a reactive site was synthetized via a suitable synthetic reaction route containing reduction, diazotization, Sonogashira coupling reaction and so on from propargyl alcohol and pentachloronitrobenzene chosen as readily available and inexpensive raw materials. Then, two haptens for OCS were obtained by labeling this analogue with coumarin and8-hydroxyquinoline derivative respectively.Finally, three haptens for PCP were synthetized by labeling intermediate3, which was obtained through Claisen rearrangement reaction in an optimized yield of69%, with coumarin, naphthalic anhydride and8-hydroxyquinoline derivative respectively.