The Recognition and Sensing of Anions by Pyrrole-2-carboxamide Derivatives

• Main Authors: Chu-Yun Hiang, 黃筑筠
• Other Authors: Chii-Tang Tsai
• Format: Others
• Language: zh-TW
• Published: 2010
• Online Access: http://ndltd.ncl.edu.tw/handle/82342755994370665276

碩士 === 中國文化大學 === 應用化學研究所 === 99 === We report the synthesis, characterization, and photophysical properties of a series of colorimetric and luminescent probes (BZ-1, BZ-2, and BZ-5) for inorganic anions. These anion probes featuring bis-amide-pyrrole recognition sites for anion recognition and quinoxaline containing chromophores for singal transduction. Anion recognition and sensing properties have been explored for a variety of biologically and/or environmentally important anions including F-, CN-, Cl-, H2PO4-. Detailed spectroscopic investigations by UV-vis absorption, fluorescence, and 1H NMR titration experiemtns have been carried to establish the sensitivity and binding modes between anions and probe molecules. BZ-1 formed hydrogen-bonding complex with OAc-, PhCOO-, H2PO4-, whereas deprotonation occurred when interacting with F-, CN-, HP2O73-, OH-. Upon coordinating of BZ-1 to Lewis acidic rhenium tricarbonyl bromide moieties, not only the amide N-H protons become more polarized but also the amide carbonyls become more electron deficient, which is susceptible to nucleophilic addition. Indeed, the interaction mode between BZ-2 and F-, CN-, OAc-, PhCOO-, H2PO4-, HP2O73-, OH- is through nucleophilic reaction to form addition products. On the other hand, the weaker nucleophilicity of Cl-, Br-, I-, NO3-, HSO4-, only formed hydrogen-bonding complexes with BZ-2. The incorporation of phenylethynyl moieties to bis-amide pyrrole unit resulted in less polarized N-Hs in BZ-5 than BZ-1 and BZ-2. Thus, BZ-5 formed only hydrogen-bonding complexes with F-, CN-, OAc-, H2PO4-, HP2O73-, OH-.