2,3,9,10,16,17,24,25-Octakis(octyloxycarbonyl)phthalocyanines. Synthesis, Spectroscopic, and Electrochemical Characteristics
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- 作者：Xueying Wang ; Yuexing Zhang ; Xuan Sun ; Yongzhong Bian ; Changqin Ma ; Jianzhuang Jiang
- 刊名：Inorganic Chemistry
- 出版年：2007
- 出版时间：August 20, 2007
- 年：2007
- 卷：46
- 期：17
- 页码：7136 - 7141
- 全文大小：86K
- 年卷期：v.46,no.17(August 20, 2007)
- ISSN：1520-510X
文摘
A series of three novel 2,3,9,10,16,17,24,25-octakis(octyloxycarbonyl)phthalocyanine compounds M[Pc(COOC8H17)8](M = 2H, Cu, Zn) (1-3) have been synthesized via the cyclic tetramerization of 4,5-di(octyloxycarbonyl)phthalonitrile,which was obtained by a newly developed procedure with o-xylene as starting material, promoted with organicbase 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in the absence and presence of metal salt like M(acac)2·H2O (M= Cu, Zn) in n-octanol at 120 
C. In addition to elemental analysis, these novel octakis(octyloxycarbonyl)-substitutedphthalocyanine compounds have been characterized by a series of spectroscopic methods. The electrochemistryof these compounds was also studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods.A significant shift to the positive direction for both the first oxidation and the first reduction of compound 1, relativeto H2Pc, reveals the electron-withdrawing nature of octyloxycarbonyl groups attached to the peripheral positions ofphthalocyanine. The effect of peripheral octyloxycarbonyl substitution on the electrochemistry of the series ofphthalocyanines 1-3 has been reasonably explained by theoretical calculation results using the density functionaltheory (DFT) method.
C. In addition to elemental analysis, these novel octakis(octyloxycarbonyl)-substitutedphthalocyanine compounds have been characterized by a series of spectroscopic methods. The electrochemistryof these compounds was also studied by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods.A significant shift to the positive direction for both the first oxidation and the first reduction of compound 1, relativeto H2Pc, reveals the electron-withdrawing nature of octyloxycarbonyl groups attached to the peripheral positions ofphthalocyanine. The effect of peripheral octyloxycarbonyl substitution on the electrochemistry of the series ofphthalocyanines 1-3 has been reasonably explained by theoretical calculation results using the density functionaltheory (DFT) method.