Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin

高等学校化学研究 ›› 2010, Vol. 26 ›› Issue (5): 761-767.

Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin

WANG Chao-wei2, REN Yu-jie1*, CAO Zhen-feng2 and CHEN Qi-bin2*

1. School of Chemistry and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235, P. R. China;
2. School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China

收稿日期:2009-10-13 修回日期:2009-11-16 出版日期:2010-09-25 发布日期:2010-11-26
通讯作者: REN Yu-jie. E-mail: clab@ecust.edu.cn; CHEN Qi-bin. E-mail: qibinchen@ecust.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.20806025).

Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin

WANG Chao-wei2, REN Yu-jie1*, CAO Zhen-feng2 and CHEN Qi-bin2*

1. School of Chemistry and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235, P. R. China;
2. School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China

Received:2009-10-13 Revised:2009-11-16 Online:2010-09-25 Published:2010-11-26
Contact: REN Yu-jie. E-mail: clab@ecust.edu.cn; CHEN Qi-bin. E-mail: qibinchen@ecust.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.20806025).

摘要/Abstract

摘要： Four “picket fence” porphyrin atropisomers were respectively synthesized from the four corresponding atropisomers of meso-tetra(o-aminophenyl)porphyrin that had been chromatographed on a column eluted with petroleum ether and ethyl acetate. Results show that each atropisomer could be successfully synthesized by controlling the acylation temperature at 0 °C. They were characterized by 1H NMR, HRMS, IR, UV-Vis and Langmuir-Blodgett(LB) film analyses. Although the results of HRMS, IR, UV-Vis analyses indicate there is no remarkable difference among the atropisomers, the results of the 1H NMR and the mean molecular areas obtained by LB film technique imply that the atropisomers are significantly discrepant. The former shows that the chemical shifts of the methyl and amide protons of each atropisomer are distinct, while the later presents that the different atropisomer molecules can occupy the different surface areas at the air/water interface.

关键词: &ldquo, Picket fence&rdquo, porphyrin, Atropisomer, Langmuir-Blodgett(LB) film, meso-Tetra(o-pivalamidophenyl) porphyrin

Abstract: Four “picket fence” porphyrin atropisomers were respectively synthesized from the four corresponding atropisomers of meso-tetra(o-aminophenyl)porphyrin that had been chromatographed on a column eluted with petroleum ether and ethyl acetate. Results show that each atropisomer could be successfully synthesized by controlling the acylation temperature at 0 °C. They were characterized by 1H NMR, HRMS, IR, UV-Vis and Langmuir-Blodgett(LB) film analyses. Although the results of HRMS, IR, UV-Vis analyses indicate there is no remarkable difference among the atropisomers, the results of the 1H NMR and the mean molecular areas obtained by LB film technique imply that the atropisomers are significantly discrepant. The former shows that the chemical shifts of the methyl and amide protons of each atropisomer are distinct, while the later presents that the different atropisomer molecules can occupy the different surface areas at the air/water interface.

Key words: “Picket fence&rdquo, porphyrin, Atropisomer, Langmuir-Blodgett(LB) film, meso-Tetra(o-pivalamidophenyl) porphyrin

WANG Chao-wei2, REN Yu-jie1*, CAO Zhen-feng2 and CHEN Qi-bin2*. Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin[J]. 高等学校化学研究, 2010, 26(5): 761-767.

WANG Chao-wei2, REN Yu-jie1*, CAO Zhen-feng2 and CHEN Qi-bin2*. Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin[J]. Chemical Research in Chinese Universities, 2010, 26(5): 761-767.

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Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin

Synthesis and Langmuir-Blodgett Film Analysis of Atropisomers of “Picket Fence” Porphyrin

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