Issue 15, 2011

Predictive power of long-range corrected functionals on the spectroscopic properties of tetrapyrrole derivatives for photodynamic therapy

Abstract

Porphyrin and chlorin based compounds possess promising properties to be utilized as photosensitizers in photodynamic therapy (PDT). However, the photosensitizers available on the market today are not ideal for use in PDT, which has emphasized the need for new photosensitizers with improved photodynamic properties to be developed. Computational drug-design can be utilized in the search for improved pharmaceutical compounds, provided that the methods used are able to reproduce experimental data. In the present study we investigated, by the use of time-dependent density functional theory (TD-DFT), the performance of the long-range corrected functionals ωB97, ωB97X and ωB97XD on their ability to predict low-lying singlet excitations (>600 nm) of a set of well-known photosensitizing compounds. It was found that ωB97X reproduced the experimental red-most absorption band most satisfactorily. The use of either B3LYP, ωB97XD or M06 in geometry optimizations has a minor effect on the spectra in most cases. Calculated energy differences between the optimized singlet ground states and optimized first excited triplet states show consistent and overall higher triplet state energies for B3LYP, M06, and PBE0 compared with ωB97, ωB97X, and ωB97XD. The calculated triplet state energies are, however, sufficient to generate singlet oxygen in most cases.

Graphical abstract: Predictive power of long-range corrected functionals on the spectroscopic properties of tetrapyrrole derivatives for photodynamic therapy

Supplementary files

Article information

Article type
Paper
Submitted
06 Dec 2010
Accepted
22 Feb 2011
First published
15 Mar 2011

Phys. Chem. Chem. Phys., 2011,13, 7207-7217

Predictive power of long-range corrected functionals on the spectroscopic properties of tetrapyrrole derivatives for photodynamic therapy

E. S. E. Eriksson and L. A. Eriksson, Phys. Chem. Chem. Phys., 2011, 13, 7207 DOI: 10.1039/C0CP02792H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements