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A push-pull unsymmetrical subphthalocyanine dimer

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  • German Zango
  • Johannes Zirzlmeier
  • Christian G. Claessens
  • Tim Clark
  • M. Victoria Martinez-Diaz
  • Dirk M. Guldi
  • Tomas Torres
Unsymmetrical subphthalocyanine fused dimers have been prepared from appropriate ortho-dinitrile SubPc precursors. In particular, either electron-donating or electron-accepting substituents have been introduced on each SubPc constituent unit, resulting in unprecedented push-pull π-extended curved aromatic macrocycles. From flurorescence experiments in solvents of different polarity we conclude a dual fluorescence, namely a delocalized singlet excited state (1.73 eV) and a polarized charge transfer state (< 1.7 eV). Pump probe experiments corroborate the dual nature of the fluorescence. On one hand, the delocalized singlet excited state gives rise to a several nanosecond lasting intersystem crossing yielding the corresponding triplet excited state. On the other hand, the polarized charge transfer state deactivates within a few picosesonds. Visualization of the charge transfer state was accomplished by means of molecular modeling with a slight polarization of the HOMO towards the electron donor and of the LUMO towards the electron acceptor.
Original languageEnglish
JournalChemical Science
Early online date17 Jun 2015
DOIs
Publication statusPublished - 2015

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