Synthesis and Metal Recognition Behavior Studies of Coumarin Substituted Ferrocene Derivatives

• Main Authors: You-chang Li, 黎祐誠
• Other Authors: Mei-Ching Lin
• Format: Others
• Language: zh-TW
• Published: 2014
• Online Access: http://ndltd.ncl.edu.tw/handle/67439628190648748143

碩士 === 朝陽科技大學 === 應用化學系碩士班 === 102 === This study use azine group to linked coumarin group and ferrocene unit, and we are also makes different modified on the ferrocene unit. Both compound S and S1were characterized by NMR, IR and Mass spectra to confirm the structure. Compound S shows obviously recognize behavior with mercury ions. In the UV-vis spectra, when Hg ions added in the solution of S, the absorption band will lead to a red shift, which is speculated the result of coordination of Hg ion with azine group and coumarin unit. In Job''s plot experiments, the binding mode of compound S and mercury ions is 1: 1, and the binding constant is 5.51 × 104 M -1. In the study of electrochemical analysis, both compound S and S1 presented a reversible redox waves, and the half-wave potential of Fe atoms varied with the different substitution on the ferrocene unit (compound S, E1/2 = 0.6445 V; compound S1, E1/2 = 0.9060 V), which mean that there are electronic communication between the coumarin chromophore with ferrocene unit. Compound S shows weak emission at room temperature (λex = 320 nm, λem = 390 nm), however, when we added Cu2+ to the solution of S, the fluorescence intensity significantly increasing. We hypothesized that in compound S, the ferrocene subunit provide an orbital to quench the fluorescence of the chromophore, after the addition of Cu2+, which acts as the oxidant, make Fe2+ oxidized to Fe3+, and suppressed the quench path of ferrocene groups, and we can observe the typical fluorescence of coumarin group.