TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: Rational design of photosensitizers for PDT and NIR region sensor applications

John MacK, Martijn Wildervanck, Tebello Nyokong

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis. Recent attempts to prepare fused-ring-expanded aza-BODIPY analogues with benzene, pyrazine, and naphthalene rings have demonstrated that the properties of aza-BODIPYs vary markedly when different fused ring systems are added to the β-carbons of the pyrrole rings. A comparison of the TD-DFT calculations demonstrates that, as has previously been postulated, trends in the optical spectra, redox properties, and electronic structures of aza-BODIPYs follow those observed for the phthalonitrile precursors and the analogous phthalocyanines despite the absence of a fully conjugated macrocyclic perimeter that obeys Hückel's rule.

Original languageEnglish
Pages (from-to)1013-1026
Number of pages14
JournalTurkish Journal of Chemistry
Volume38
Issue number6
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • Aza-BODIPYs
  • Phthalocyanines
  • TD-DFT calculations

ASJC Scopus subject areas

  • Chemistry(all)

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