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Issue 20, 2009
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Synthesis, mesomorphism and electrochemical properties of tetrasubstituted zinc and copper phthalocyanines

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Abstract

We describe the synthesis of highly soluble, tetrasubstituted zinc and copper phthalocyanines exhibiting liquid crystalline properties. These compounds were characterized using elemental analysis, MS, 1H-NMR, FTIR and UV-Vis absorption spectroscopy. The liquid crystalline properties of phthalocyanines (Pcs) were studied by polarizing optical microscopy and differential scanning calorimetry. All of the four compounds exhibit thermotropic columnar mesophases and two of them show clear hexagonal ordering. Additionally, these Pcs display lyotropic behaviour. The clearing temperatures lie above 300 °C and on cooling down the mesophase can be “frozen” into a glassy state. The cyclic voltammetry studies of these phthalocyanines show electrochemical stability and reversible redox behaviour. The Pcs without any azo groups in the ligands exhibit both reversible oxidation and reduction, whereas those with azo groups show only reversible reduction steps. The low HOMO energy values of about 5 eV as calculated from oxidation potential make these compounds interesting as p-type organic semiconductors for electro-optical applications.

Graphical abstract: Synthesis, mesomorphism and electrochemical properties of tetrasubstituted zinc and copper phthalocyanines

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Publication details

The article was received on 27 Nov 2008, accepted on 06 Mar 2009 and first published on 01 Apr 2009


Article type: Paper
DOI: 10.1039/B821306B
J. Mater. Chem., 2009,19, 3161-3167

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    Synthesis, mesomorphism and electrochemical properties of tetrasubstituted zinc and copper phthalocyanines

    N. Zharnikova, N. Usol'tseva, E. Kudrik and M. Thelakkat, J. Mater. Chem., 2009, 19, 3161
    DOI: 10.1039/B821306B

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