Aggregation behavior in unsymmetrically substituted metal-free phthalocyanines

Rabia Zeynep Uslu Kobak, Meral Uʇuz Ari, Adem Tekin*, Ahmet Gül

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Phthalocyanines (Pcs) generally have a strong tendency for stacking in solution to form dimer and high order oligomers owing to the π-π, metal-ligand coordination, hydrogen bonding and donor-acceptor interactions between planar rings. Large substituents in peripheral positions, solvents and their amount and the central metal affect the aggregation to a remarkable extent. In Pcs, aggregation results in lowering the solubility, bringing purification and characterization problems and decreasing the photosensitizing efficiency. The aim of this study is to determine the predominant reasons inhibiting the aggregation in an unsymmetrically substituted metal-free Pc which contains three naphthoxy units and one carboxy-1,2-dioxyphenyl in THF. Dispersion-corrected density functional theory interaction energy calculations performed at B97-D/TZVP level revealed that aggregation in these complexes are prevented due to the strong solvent-phthalocyanine interactions rather than the existence of large substituents.

Original languageEnglish
Pages (from-to)91-97
Number of pages7
JournalChemical Physics
Volume448
DOIs
Publication statusPublished - 20 Feb 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier B.V. All rights reserved.

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 1002132012, TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources) and Informatics Institute of Istanbul Technical University.

FundersFunder number
TUBITAK ULAKBIM
Istanbul Teknik Üniversitesi1002132012

    Keywords

    • Aggregation
    • B97-D
    • Density functional theory
    • Interaction energy
    • Phthalocyanine

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