Photophysicochemical properties and TD-DFT calculations of a novel terminal alkyne substituted metal free phthalocyanine

Yusuf Yilmaz, John Mack, Mehmet Sönmez, Tebello Nyokong

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The synthesis of a novel free base tetrakis(prop-2-ynyloxy)phthalocyanine (2) is described, along with its characterization by IR, UV-visible absorption, and 1H NMR spectroscopy and mass spectrometry. The compound exhibited good solubility in a wide range of organic solvents and no significant aggregation was observed over a wide concentration range. The values for the singlet oxygen (ΦΔ), photodegradation, fluorescence (ΦF) and triplet state quantum yields and the fluorescence and triplet state lifetimes are reported. A relatively high ΦΔ value of 0.46 was obtained in DMSO. The ability to carry out "click" chemistry at the ligand periphery enhances the potential utility of 2 for use in bioconjugates in photodynamic therapy (PDT). A moderately high ΦF value of 0.18 is observed for emission in the therapeutic window in the near-IR region, which suggests that it may also be possible to determine the level of localization of 2 in tumor cells through bioimaging.

Original languageEnglish
Pages (from-to)251-258
Number of pages8
JournalJournal of Porphyrins and Phthalocyanines
Volume18
Issue number3
DOIs
Publication statusPublished - 2014 Mar

Keywords

  • TD-DFT calculations
  • phthalocyanine
  • singlet oxygen quantum yields

ASJC Scopus subject areas

  • Chemistry(all)

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