Abstract
Vinylene-bridged hexaphyrin(2.1.2.1.2.1) was synthesized from dipyrrolyl diphenylethenes by acid-catalyzed condensation reactions. Freebase hexaphyrin(2.1.2.1.2.1) forms a distorted structure with non-aromatic characteristics. The aromaticity and molecular configuration of non-planar hexaphyrin(2.1.2.1.2.1) can be controlled by insertion of metal ions. Freebase and zinc complexes show a distorted structure without macrocyclic aromaticity, whereas copper complexes show a figure-of-eight structure with macrocyclic aromaticity. It is the first example of aromaticity conversion of a distorted expanded porphyrin involving vinylene bridges.
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