Synthesis and Anion-Selective Complexation of Ferrocenecarbamide Derivatives

• Main Authors: Kuo, Li-Jun, 郭麗君
• Other Authors: Fang, Jim-Min
• Format: Others
• Language: zh-TW
• Published: 2002
• Online Access: http://ndltd.ncl.edu.tw/handle/22205257128405006131

碩士 === 國立臺灣大學 === 化學研究所 === 90 === As a result of the biological and environmental significance of anions, selective recognition and sensing of anions are of great importance in modern host-guest chemistry. It is known that the amido protons can serve as hydrogen-bond donors for acetate, nitrate, fluoride and dihydrogenphosphate ions. In this thesis, we synthesized a series of artificial neutral anion receptors with multiple amide scaffolds. The structure was established by incorporating four additional amido groups to the main skeleton of ferrocene 2,6-biscarboxamide. From 1H NMR spectroscopy, we found that our synthetic receptors bound H2PO4- anions most strongly. The binding properties of these receptors with H2PO4- anions were evaluated by the 1H NMR studies in DMSO-d6 solutions. The 1:1 complexation stoichiometry of receptors 8, 12, 15 with H2PO4- anions and the 1:2 complexation stoichiometry of receptors 7, 11, 16 with H2PO4- anions were confirmed by a continuous variation method (Job’s plot). We also found that receptors 11 and 12 bearing electron-withdrawing groups can act as better H2PO4- receptors. Optical and redox properties of these receptors were assessed by fluorescence measurements and cyclic voltammetry.