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

E-ISSN： 1521-3773|54|17|5187-5191

ISSN： 1433-7851

Source： ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.54, Iss.17, 2015-04, pp. : 5187-5191

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Abstract

AbstractThe 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.