新型双核二茂铁基席夫碱的合成及其电化学性质

Synthesis and Electrochemical Properties of Novel Bisferrocenyl Schiffbases

乙炔二茂铁分别与对溴苯甲醛和对碘苯胺经Sonogashira反应制得中间体4-(2-二茂铁基-乙炔基)苯甲醛(2a)和4-(2-二茂铁基-乙炔基)苯胺(2b);2a和2b分别与对苯二胺和对苯二甲醛经胺醛缩合反应合成了两个新型的双核二茂铁基席夫碱类配合物(3a和3b),其结构经1H NMR和元素分析表征。电化学研究结果表明,3a(3b)的Epa,Epc,E1/2和ipc/ipa分别为0.279 V(0.311 V),0.195 V(0.196 V),0.238 V(0.260 V)和0.96(1.06);中间桥连基团对3的电化学性质影响显著。

Two intermediates,4-（2-ferrocenyl-ethynyl） benzaldehyde （2a） and 4-（2-ferrocenyl-ethynyl） aniline（2b）,were synthesized by Sonogashira coupling reaction of ethynylferrocene with 4-bromobenzaldehyde or 4-iodoaniline,respectively.Two novel bisferrocenyl schiffbase complexes（3a and 3b） were synthesized by aldimine condensation reaction of2a with p-phenylenediamine or 2b with 1,4-phthalaldehyde,respectively.The structures were characterized by 1H NMR and elemental analysis.The electrochemical properties were investigated by voltammogram.The results showed that Epa,Epc,E1/2 and ipc/ipaof3a（3b） were 0.279 V（0.311 V）,0.195 V（0.196 V）,0.238 V（0.260 V） and 0.96 （1.06）,respectively.The electrochemical properties of 3 were significantly effected by the different central bridge unit.