合成水溶性含氮雜環化合物及其在分子辨識上之應用(ㄧ)水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識(二)口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試

Synthesis of Water Soluble Nitrogen Heterocyclic Compounds for Applications in Molecular Recognition I. Preparation of Water Soluble Bispyrrole-bipyridine Derivatives for Recognition of Metal Ions in Water II Synthesis of Water Soluble Bispyrrole-naphthyridine Derivatives and The Binding Study in Two-Phase System

王大明(Da-Ming, Wang)

指導教授 ： 方俊民

國立臺灣大學/理學院/化學研究所/碩士(2006年)

https://doi.org/10.6342/NTU.2006.02341

摘要

本篇論文主要分為二部份，分別是水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識，以及口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試。
第一部份︰水溶性双吡咯-聯吡啶衍生物製備及其在水溶液中對金屬離子的辨識
在第一部分的研究中，藉著在吡咯環上引進水溶性的ethylene glycol基團以增進BPBP的水溶性，以便於在水溶液中對金屬離子的檢測及研究。我們成功地合成出水溶性BPBP衍生物，其在幾乎為水的條件下 (氰甲烷/水 = 1: 99 )，仍然對銀、銅以及汞離子有辨識效果，且與金屬離子結合後紫外-可見光吸收會造成紅位移的變化。
第二部份︰口奈啶-双吡咯水溶性衍生物之合成以及它在兩相系統的嘗試
口奈啶-双吡咯化合物BPN為本實驗室開發出對醣苷有辨識能力的螢光分子，其具有極佳的光物理性質使得BPN在二氯甲烷下，對正辛烷基葡萄糖苷的螢光偵測極限可達100 pM，但其缺點為水溶性太差，因此醣需經長碳鏈衍生化以增加其對有機溶劑的溶解度以進行檢測。在第二部份中，我們以BPN為主體，藉著引入水溶性的ethylene glycol基團以增進BPN的水溶性。另外也嘗試將BPN應用至兩相系統的萃取中，但空白實驗的結果顯示即使是少量的水藉著萃取溶進二氯甲烷中，也會對BPN的螢光強度變化造成干擾。

關鍵字

水溶性 ； 分子辨識 ； 兩相系統

並列摘要

This thesis consists of two parts. The first part is to prepare water soluble bispyrrole-bipyridine derivatives for recognition of metal ions in water; the second part is to synthesize water soluble bispyrrole-naphthyridine derivatives, and the binding study in two-phase system is also attempted.
Part I: Preparation of water soluble bispyrrole-bipyridine derivatives for recognition of metal ions in water
By introduction of ethylene glycol moiety to the pyrrole ring of BPBP molecule, the solubility of such BPBP derivative in water is enhanced, thus sensing metal ions in water becomes possible. The synthesis of a water-soluble BPBP derivative is carried out, and the BPBP compound showed binding affinity toward silver(I), copper(II), and mercury(II) ions in aqueous solution ( CH3CN/H2O = 1: 99 ). The BPBP receptor shows shifts in the UV-Vis spectra on binding with appropriate metal ions.
Part II: Synthesis of water soluble bispyrrole-naphthyridine derivatives and the binding study in two-phase system
Bispyrrole-naphthyridine molecule BPN (2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine) is a fluorescent molecule designed to bind selectively with octyl glucopyranoside in our lab. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of 100 pM. However, BPN has poor water solubility, thus we have to use alkyl glucopyranoside for the binding study in organic solvents. We thus attempted to incorporate ethylene glycol group to BPN to render an enhanced solubility in water. We also attempted to examine the binding of BPN with sugar in two-phase system. However, the blank tests showed that even little water extracted in dichloromethane would interfere with the fluorescence intensity of BPN.

並列關鍵字

Water-Soluble ； Molecular Recognition ； Two-Phase System

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