Hydrophilic annulated dinuclear zinc(II) phthalocyanine as Type II photosensitizers for PDT: a combined experimental and (TD)-DFT investigation

Quartarolo A. D., Perusse D., DUMOULIN F., Russo N., Sicilia E.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.17, no.10, pp.980-988, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 10
  • Publication Date: 2013
  • Doi Number: 10.1142/s1088424613500569
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.980-988
  • Keywords: photodynamic therapy, annulated zinc phthalocyanine, time-dependent density functional, DENSITY-FUNCTIONAL THEORY, PHOTODYNAMIC THERAPY, ABSORPTION-SPECTRA, SINGLET OXYGEN, COMPLEXES, PORPHYRIN, SUBSTITUENTS, RETENTION
  • Acibadem Mehmet Ali Aydinlar University Affiliated: Yes

Abstract

The design, synthesis and theoretical calculations of a mononuclear and its corresponding annulated dinuclear hydrophilic zinc(II) phthalocyanines (ZnPcs) are reported here, the hydrophilic substituent being 1,3-bis((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)propan-2-ol. These novel compounds have been characterized by UV-vis spectroscopy in ethanol and ethanol: water (50: 50) solutions. The electronic spectra of the mononuclear derivatives retain the main spectral features of ZnPc with a strong Q-band absorbance at 678 nm in ethanol and a less intense B-band at 370 nm. The annulated dinuclear derivatives show a broad Q-band absorbance with main wavelength maxima between 600 and 720 nm. From time-dependent density functional (TDDFT) UV-vis spectra simulation performed on selected isomers, Q-band absorption maxima of the non-peripherally substituted forms are more red-shifted compared to those of peripheral forms.