Issue 3, 2011
From the journal:

Dalton Transactions

Synthesis and characterization, novel across adjacent ring formed phthalocyanine

Dilek Elmalı,a   Ahmet Altındal,b   Ali Rıza Özkaya,c   Bekir Salihd  and  Özer Bekaroğlu*e  

* Corresponding authors

a Department of Chemistry, Anadolu University, Eskişehir, Turkey
E-mail: angelnew2000@yahoo.com

b Department of Physics, Marmara University, Göztepe-Istanbul, Turkey
E-mail: aaltindal@marmara.edu.tr
Fax: +90216347878

c Department of Chemisry, Marmara University, Göztepe-Istanbul, Turkey
E-mail: aliozkaya@marmara.edu.tr
Tel: +902163478783

d Department of Chemistry, Hacettepe University, Ankara, Turkey
E-mail: bekir@hacettepe.edu.tr
Fax: +90 3122992163

e Department of Chemistry, Technical University of Istanbul, Maslak-Istanbul, Turkey
E-mail: obek@itu.edu.tr
Fax: +90 216 3860824

Abstract

Novel mononuclear Zn(II) 4, Co(II) 5 and Cu(II) 6metallophthalocyanines have been synthesized from 4,4′(ethane-1,1-p-phenol-2,2-p-phenoxy)phthalonitrile 3, which can be obtained by the reaction of 4-nitrophthalonitrile 1 with 1,1,2,2-tetrakis(p-hydroxy-phenyl)-ethane 2. The target water-soluble derivatives of 7–9 were acquired from a boiling suspension of the compounds in aqueous 20% KOH solution. The synthesized complexes have been characterized by UV-vis, IR, 1H NMR and MALDI-TOF-mass spectroscopies. In addition, the geometric and electronic structures of 2–6 were investigated by ab initio/DFT quantum mechanical calculations using the Gaussian 03 program with HF theory at the B3LYP/3-21G level. The redox properties of the complexes 4–6 were examined by cyclic voltammetry on platinum in DMSO/TBAP. These complexes displayed one-electron metallophthalocyanine-based and multi-electron hydroxyphenyl-based redox processes. The effect of temperature on the d.c. conductivity and impedance spectra of spin coated films of compounds were investigated at the temperatures between 300–452 K and in the frequency range of 40–105 Hz. Thermally activated conductivity dependence on temperature was observed for all compounds. A.c. results indicated that conduction mechanism can be explained by classical hopping barriers mechanism for all films.

Graphical abstract: Synthesis and characterization, novel across adjacent ring formed phthalocyanine

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Article information

DOI
https://doi.org/10.1039/C0DT01163K
Article type
Paper
Submitted
03 Sep 2010
Accepted
01 Oct 2010
First published
02 Dec 2010

Dalton Trans., 2011,40, 651-660

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Synthesis and characterization, novel across adjacent ring formed phthalocyanine

D. Elmalı, A. Altındal, A. R. Özkaya, B. Salih and Ö. Bekaroğlu, Dalton Trans., 2011, 40, 651 DOI: 10.1039/C0DT01163K

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