Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 346-351.DOI: 10.6023/cjoc201509007 Previous Articles     Next Articles



陈东, 拓巧艳, 刘温馨, 殷钦, 佟旭光, 赵海英, 李保国, 边占喜   

  1. 内蒙古大学化学化工学院 内蒙古自治区精细有机合成重点实验室 呼和浩特 010021
  • 收稿日期:2015-09-06 修回日期:2015-10-14 发布日期:2015-10-26
  • 通讯作者: 赵海英
  • 基金资助:

    国家自然科学基金(No. 21562032)、内蒙古自治区高等学校科学研究(No. NJZZ001)和内蒙古自治区自然科学基金(Nos. 2013MS0207, 2014JQ02)资助项目.

Synthesis and Properties of Porphyrin Containing Long Chain Alkylferrocene

Chen Dong, Tuo Qiaoyan, Liu Wenxin, Yin Qin, Tong Xuguang, Zhao Haiying, Li Baoguo, Bian Zhanxi   

  1. College of Chemistry and Chemical Engineering, Inner Mongolia University, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot 010021
  • Received:2015-09-06 Revised:2015-10-14 Published:2015-10-26
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21562032), the Research Program of Science and Technology at Universities of Inner Mongolia (No. NJZZ001) and the Natural Science Foundation of Inner Mongolia (Nos. 2013MS0207, 2014JQ02).

Two series of porphyrins and their Zn (II) complexes modified with long chain alkylferrocene were designed. One was close conjugate connection of porphyrin and ferrocene containing long chain alkyl group by an amide linkage in meso site of porphyrin (porphyrin 5 and its Zn (II) complex 6), the other was placed ferrocene on the skirt of meso-tetraphenylporphyrin with long chain alkoxy group (porphyrin 7 and its Zn(II) complex 8). The spectroscopic and electrochemistry properties of two series of compounds were investigated. The absorption bands of free porphyrins were almost the same, but those of their Zn(II) complexes were red-shifted by 7 nm. Porphyrins 5 and 6 with an amide linkage exhibited strong fluorescence quenching with a low quantum yield compared with those containing a long chain alkoxy group linkage (7 and 8). Compared with the free porphyrins, the negative potential shifts of the Zn(II) complexes were observed in cyclic voltammetry experiments. In addition, the first oxidation potentials of porphyrin in 7 and 8 were slight negative shifts relative to 5 and 6, but the first oxidation potentials of ferrocene in 7 and 8 shifted about 182~194 mV.

Key words: ferrocene, porphyrin, UV-Vis absorption spectrum, fluorescence spectrum, electrochemistry