A core-expanded subphthalocyanine analogue with a significantly distorted conjugated surface and unprecedented properties

The introduction of a seven-membered-ring unit in the place of a five-membered-ring unit in the structure of subphthalocyanine resulted in significant distortion of the bowl-shaped structure of the conjugated molecule as well as the following unprecedented properties: the preferential formation of the axially fluoro substituted species, the fluttering-dynamic-motion-induced rapid exchange of P and M enantiomers, markedly split Q-band absorption, and a clear difference in the ring-current effects arising from the convex and concave surfaces. All in a flutter: Significant distortion of the bowl-shaped structure of subphthalocyanine upon the introduction of a seven-membered ring in place of two five-membered rings (see scheme) led to unusual properties and reactivity. Fluttering-dynamic-motion-induced rapid exchange of the P and M enantiomers as well as markedly split Q-band absorption and distinct ring-current effects arising from the convex and concave surfaces were observed.