Cyclophanes Containing Bowl-Shaped Aromatic Chromophores: Three Isomers of anti-[2.2](1,4)Subphthalocyaninophane

The connection of bowl-shaped aromatic boron subphthalocyanines with anti-[2.2]paracyclophane resulted in the first observation of electronic communication between convex and concave surfaces. Three isomers of anti-[2.2](1,4)subphthalocyaninophane, described as concave - concave (CC), convex - concave (CV), and convex - convex (VV) according to the orientation of the subphthalocyanine units, were synthesized and characterized by various spectroscopic techniques, including ¹H NMR, electronic absorption, fluorescence, and magnetic circular dichroism spectroscopy and X-ray crystallography, together with molecular-orbital calculations. On going from the CC system to CV and further to VV, the Q band broadened and finally split as a result of through-space expansion of the conjugated systems, which were also reproduced theoretically.