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 language | English |
|---|---|
| Pages (from-to) | 91-97 |
| Number of pages | 7 |
| Journal | Chemical Physics |
| Volume | 448 |
| DOIs | |
| Publication status | Published - 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.
| Funders | Funder number |
|---|---|
| TUBITAK ULAKBIM | |
| Istanbul Teknik Üniversitesi | 1002132012 |
Keywords
- Aggregation
- B97-D
- Density functional theory
- Interaction energy
- Phthalocyanine