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以二茂铁为原料,经酰化反应得到二茂铁甲醛,再与含不同取代基的邻苯二胺进行加成、消除反应合成了3种二茂铁苯并咪唑衍生物FcB1~FcB3,通过~1H NMR、13C NMR和IR表征其结构。采用循环伏安法、计时电流法和紫外可见光谱研究了3种二茂铁苯并咪唑衍生物的电化学性能和离子识别性能。结果表明,3种物质在电极表面均发生了单电子可逆氧化还原反应,且在电极表面的反应受扩散控制,扩散系数分别为1.201 cm~2/s、1.533 cm~2/s和2.190 cm~2/s;在各种阴离子中,FcB1~FcB3对F-显示出多种信号响应识别,F-的加入使其紫外光谱448 nm处发生红移,吸光度增大,同时使其Fe~(3+)/Fe~(2+)电位分别向负极移动193 mV、174 m 、153 mV。核磁氢谱滴定结果表明,FcB1~FcB3中苯并咪唑环上的N-H质子与F-形成氢键从而达到识别功能。
Using ferrocene as raw material, ferrocene formaldehyde was obtained by acylation reaction, and then o-phenylenediamine with different substituents were added to eliminate the reaction to synthesize three kinds of ferrocene benzimidazole derivatives FcB1 ~ FcB3, Its structure was characterized by ~ 1H NMR, 13C NMR and IR. Cyclic voltammetry, chronoamperometry and UV-Vis spectroscopy were used to study the electrochemical and ionic recognition properties of the three ferrocene benzimidazole derivatives. The results showed that all three kinds of materials were single electron reversible redox reaction on the electrode surface, and the reaction on the electrode surface was controlled by diffusion. The diffusion coefficients were 1.201 cm 2 / s, 1.533 cm 2 / s and 2.190 cm ~ 2 / s. Among the various anions, FcB1 ~ FcB3 showed a variety of signal responses to F-. F-incorporation led to a red shift in the UV spectrum at 448 nm, an increase of absorbance, +) / Fe ~ (2+) potential to the negative electrode 193 mV, 174 m, 153 mV. The results of 1H NMR showed that the N-H proton on the benzimidazole ring in FcB1 ~ FcB3 could form hydrogen bond with F- to achieve the recognition function.