Citation: Chen Dong, Tuo Qiaoyan, Liu Wenxin, Yin Qin, Tong Xuguang Zhao, Haiying Li, Baoguo Bian, . Synthesis and Properties of Porphyrin Containing Long Chain Alkylferrocene[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 346-351. doi: 10.6023/cjoc201509007 shu

Synthesis and Properties of Porphyrin Containing Long Chain Alkylferrocene

1.
College of Chemistry and Chemical Engineering, Inner Mongolia University, Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot 010021

Corresponding author: Haiying Li,
Received Date: 6 September 2015
Available Online: 14 October 2015
Fund Project: 国家自然科学基金(No. 21562032) (No. 21562032)内蒙古自治区高等学校科学研究(No. NJZZ001) (No. NJZZ001)内蒙古自治区自然科学基金(Nos. 2013MS0207, 2014JQ02)资助项目. (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.
- ferrocene,
- porphyrin,
- UV-Vis absorption spectrum,
- fluorescence spectrum,
- electrochemistry
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沈阳化工大学材料科学与工程学院沈阳 110142