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Keywords:

  • absorption;
  • annulenes;
  • density functional calculations;
  • dyes/pigments;
  • porphyrinoids
Thumbnail image of graphical abstract

Are you N-fused? Doubly N-fused porphyrin (see picture; Br red, F green, N blue) exhibits exceptionally long-wavelength absorption for an 18π aromatic system (in excess of 1600 nm). The HOMO–LUMO energy gap of doubly N-fused porphyrin is extremely small for an [18]annulenic compound and results from endocyclic extension of the porphyrin π system.