Effect of NO2 substitution and solvent on UV-visible spectra, redox potentials and electron transfer mechanisms of copper β-nitrotriarylcorroles. Proposed electrogeneration of a Cu(I) oxidation state

Author:

Ye Lina12,Ou Zhongping2,Fang Yuanyuan2,Song Yang3,Li Bihong2,Liu Rui2,Kadish Karl M.3

Affiliation:

1. College of Computer, Jilin Normal University, Siping 136000, China

2. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China

3. Department of Chemistry, University of Houston, Houston, TX 77204-5003, USA

Abstract

Three copper triarylcorroles containing a [Formula: see text]-pyrrole nitro substituent were synthesized and characterized as to their spectral and electrochemical properties in nonaqueous media. The examined compounds are represented as [Formula: see text]-NO2(YPh)3CorCu, where Cor is the trianion of a triphenylcorrole and Y is a Cl, H or CH3 substituent at the para-position of the three meso-phenyl rings of the compound. The data from absorption spectra, electrochemistry and thin-layer spectroelectrochemistry are consistent with an initial assignment of Cu[Formula: see text]-Cor[Formula: see text] in CH2Cl2, DMF and pyridine and electrogeneration of a formal Cu(II) corrole with an unreduced macrocycle, represented as Cu[Formula: see text]-Cor[Formula: see text], after the first one-electron reduction in these solvents. The doubly reduced [Formula: see text]-nitrocorrole has a sharp Soret band at 439 nm and a well-defined Q-band at 611 nm in CH2Cl2. Similar absorption spectra are seen for the three examined doubly reduced nitrocorroles in DMF and pyridine, suggesting formation of a Cu(I) species with an unreduced macrocycle which is represented as Cu[Formula: see text]-Cor[Formula: see text]. Changes in redox potentials and absorption spectra of the nitrocorroles are examined as a function of solvent and substituents on the meso-phenyl rings of the compounds and comparisons are made between spectral and electrochemical data of the newly synthesized corroles and that of structurally related tetraarylcorroles lacking a [Formula: see text]-nitro group.

Publisher

World Scientific Pub Co Pte Lt

Subject

General Chemistry

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