MCD spectroscopy and TD-DFT calculations of low symmetry subnaphthalocyanine analogs

• MCD spectra of subnaphthalocyanine analogs with tetrafluorobenzo moieties are reported.
• Attempts to generate stable anion radical species proved unsuccessful.
• DFT and TD-DFT calculations for a subanthracocyanine model complex are reported.
• Results suggest that the NIR region absorbing subphthalocyanine analogs can be prepared.

Magnetic circular dichroism (MCD) spectroscopy and time-dependent density functional theory (TD-DFT) calculations are used to analyze the electronic structure and optical properties of low-symmetry subnaphthalocyanine analogs with AAB and ABB structures formed during mixed condensations of tetrafluorophthalonitrile and 2,3-naphthalenedicarbonitrile. The results demonstrate that trends observed in the properties of phthalocyanine analogs can be used to fine tune the optical properties so that the Q(0,0) bands lie in the red region, in a manner that does not significantly destabilize the highest occupied molecular orbital (HOMO) energy relative to that of the parent subphthalocyanine ligand. Attempts to study the spectroscopy of anion radical species proved unsuccessful, since they proved to be unstable.

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