Synthesis and aggregation behavior of zinc phthalocyanines substituted with bulky naphthoxy and phenylazonaphthoxy groups: An experimental and theoretical study

Ibrahim Özçeşmeci*, Adem Tekin, Ahmet Gül

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Zinc (II) phthalocyanines, bearing peripherally β-naphthol and ({1-[(Z or E)-phenylazo]-2-naphthyl}oxy) have been synthesized and characterized. Aggregation properties of these compounds were investigated in different concentration ranges. The molecular orbital properties and ultraviolet-visible spectra of these phthalocyanines were studied using density functional and time-dependent density functional theories. The computed electronic spectra are in good agreement with the experimental data. Moreover, dimerization of these phthalocyanine complexes in solvent (tetrahydrofuran) medium was investigated by counterpoise corrected interaction energy calculations employing dispersion corrected Becke's 1997 hybrid functional with valence triple-zeta basis set. These calculations revealed that aggregation in these complexes are prevented due to the strong solvent-phthalocyanine interactions and this finding was supported by our experiments.

Original languageEnglish
Pages (from-to)100-110
Number of pages11
JournalSynthetic Metals
Volume189
DOIs
Publication statusPublished - Mar 2014

Funding

This work was supported by the Research Fund of the Technical University of Istanbul . Computing resources are provided by the National Center for High Performance Computing of Turkey (UHEM) , under the Grant Number 20662009 and Informatics Institute of Istanbul Technical University . AG thanks Turkish Academy of Sciences (TUBA) for partial support.

FundersFunder number
Informatics Institute of Istanbul Technical University
Technical University of Istanbul20662009

    Keywords

    • β-Naphthol
    • Aggregation
    • Azobenzene
    • Density functional theory
    • Phthalocyanine
    • Red shifts

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