Abstract
The fundamental properties of azaporphyrins can be modulated over a
wide range by changing the number of meso-nitrogen atoms. Reported
herein are the first examples of
5,10,15,20-tetraaryl-5-azaporphyrinium (MTAMAP) salts, which were
prepared via metal-templated cyclization of the corresponding zinc(II)
and copper(II) complexes of
10-aryl-1-chloro-19-benzoyl-5,15-dimesityl-10-azabiladiene-ac. The
inclusion of one meso-nitrogen atom in the
5,10,15,20-tetraarylporphyrin skeleton considerably changes the redox
and optical properties as well as the degree of aromaticity of the
porphyrin ring. The present findings suggest that MTAMAP salts would
be promising scaffolds for the development of new azaporphyrin-based
ionic fluorophores and photosensitizers.