Exploring the Photophysics of Polyfluorinated Phthalocyanine Derivatives as Potential Theranostic Agents

Basak Koca, Esin Hamuryudan, Saron Catak, Ali Erdogmus, Antonio Monari*, Viktorya Aviyente

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)


State-of-the-art computational tools were used to investigate the photophysical properties of polyfluorinated phthalocyanines (Pc) to predict their potential use as photosensitizers in photodynamic therapy. The main factors, such as the identity of the metal ion, the effect of substituents, the environment, and solvent effects that enhance the efficiency of phthalocyanines as photosensitizers, were considered, particularly taking into account their influence on the triplet-state energy and intersystem crossing probability. The population of the triplet state ultimately determines the phthalocyanine's propensity to activate singlet oxygen, which is responsible for inducing death of the cancer cell. Time-dependent density functional theory was used to elucidate the photophysical properties of pentafluorobenzyloxy-substituted phthalocyanines (R2Pc) as well as their unsubstituted analogues. Vibrational and dynamic effects influencing the absorption and emission spectra were included by sampling the potential energy surfaces via the Wigner distribution approach. Furthermore, the intersystem crossing pathways were analyzed by using the singlet-triplet band gap and the spin-orbit coupling constant. Finally, the singlet oxygen generation capability was experimentally verified for the R2-ZnPc complex both in DMSO and in different ratios of DMSO/water mixtures. The singlet oxygen quantum yield of R2-ZnPc in DMSO was also evaluated and compared with that of the unsubstituted ZnPc.

Original languageEnglish
Pages (from-to)24417-24425
Number of pages9
JournalJournal of Physical Chemistry C
Issue number40
Publication statusPublished - 10 Oct 2019

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.


The authors acknowledge support from the University of Lorraine (Nancy) and Bogazici (Istanbul). The numerical calculations reported in this paper were partially performed at the LPCT local computing resources as well as at the TUBITAK ULAKBIM High Performance and Grid Computing Center (TRUBA resources). EH and AE thank TUBITAK (Project Number: 216S448) for support.

FundersFunder number
Université de Lorraine


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