Synthesis and Physical Properties of β-Substituted Porphyrin Nickel(II) Derivatives

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (03): 356-361. Previous Articles Next Articles

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β-位取代卟啉镍衍生物的合成及其物性研究

万中全¹，贾春阳*^,1，张家强¹，李孜¹，王志红¹，张关心²

(¹电子科技大学电子薄膜与集成器件国家重点实验室微电子与固体电子学院成都 610054)
(²中国科学院化学研究所北京 100190)

收稿日期:2010-07-10 修回日期:2010-11-05 发布日期:2010-11-18
通讯作者: 贾春阳 E-mail:cyjia@uestc.edu.cn

Synthesis and Physical Properties of β-Substituted Porphyrin Nickel(II) Derivatives

Wan Zhongquan¹ Jia Chunyang*^,1 Zhang Jiaqiang1 Li Zi¹ Wang Zhihong¹ Zhang Guanxin²

(¹State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Microelectronics and Solid-State Electronics, University of Electronic Science and Technology of China, Chengdu 610054)
(²Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190)

Received:2010-07-10 Revised:2010-11-05 Published:2010-11-18

Abstract

[5,10,15,20-Tetrakis(4-decaneoxyphenyl)-β-nitro-porphyrinato]nickel(II) (1) and {5,10,15,20- tetrakis(4-decaneoxypheny1)-6 -nitroquinoxalino[2,3-b ]porphyrinato}nickel(II) (2) are synthesized and confirmed by ¹H NMR, infrared spectroscopy, mass spectrometry (MS), and elemental analysis. The first oxidation potentials of 1 and 2 are positive-shifted and the maximum absorptions of 1 and 2 are red-shifted compare with those of starting compound 3. Differential scanning calorimetry (DSC) results show that only compound 1 possesses liquid crystal property, which behaves the heating monotropic liquid crystal. The self-assembly films of the compounds on Si are studied by atomic force microscopy (AFM), the self-assembly film of 1 is better ordered compared with that of 2. These results indicate that the different physical properties of compounds 1 and 2 are mainly due to their different β-substituted groups. The observed electronic properties are explained by calculated results based on density functional theory (DFT).

Key words: porphyrin, cyclic voltammetry, liquid crystal, self-assembly, density functional theory (DFT)

Cite this article

WAN Zhong-Quan, JIA Chun-Yang, ZHANG Jia-Qiang, LI Zi, WANG Zhi-Hong, ZHANG Guan-Xin. Synthesis and Physical Properties of β-Substituted Porphyrin Nickel(II) Derivatives[J]. Chin. J. Org. Chem., 2011, 31(03): 356-361.

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β-位取代卟啉镍衍生物的合成及其物性研究

Synthesis and Physical Properties of β-Substituted Porphyrin Nickel(II) Derivatives

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