Turkish Journal of Chemistry
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 \beta-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.
DOI
10.3906/kim-1406-32
Keywords
TD-DFT calculations, phthalocyanines, aza-BODIPYs
First Page
1013
Last Page
1026
Recommended Citation
MACK, J, WILDERVANCK, M, & NYOKONG, T (2014). TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications. Turkish Journal of Chemistry 38 (6): 1013-1026. https://doi.org/10.3906/kim-1406-32
