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2,3,9,10,16,1 7,24,25-Octakis(octyloxycarbonyl)phthalocyanines. Synthesis, Spectroscopic, and Electrochemical Characteristics.
- Source :
-
Inorganic Chemistry . 8/20/2007, Vol. 46 Issue 17, p7136-7141. 6p. 2 Diagrams, 3 Charts, 4 Graphs. - Publication Year :
- 2007
-
Abstract
- 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 ο-xylene as starting material, promoted with organic base 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)-substituted phthalocyanine compounds have been characterized by a series of spectroscopic methods. The electrochemistry of 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, relative to H2Pc, reveals the electron-withdrawing nature of octyloxycarbonyl groups attached to the peripheral positions of phthalocyanine. The effect of peripheral octyloxycarbonyl substitution on the electrochemistry of the series of phthalocyanines 1-3 has been reasonably explained by theoretical calculation results using the density functional theory (DFT) method. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00201669
- Volume :
- 46
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Inorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27082027
- Full Text :
- https://doi.org/10.1021/ic700517e