Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 3, Pages 464-465Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja067102v
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5,20-Diethynyl substituted [26]hexaphyrins(1.1.1.1.1.1) undergo a thermal or spontaneous crossbridging eaction to provide trans-vinylene-bridged [26]hexaphyrins, probably through strongly folded conformations. Facile aromatic-antiaromatic switching of vinylene-bridged hexaphyrins has been demonstrated upon two-electron redox processes. Curiously, a resonance contributor of the vinylenebridged hexaphyrins is regarded as [16]diazaannuleno[16]diazaannulene but its contribution should be minor because of the perpendicular geometry of the bridge. Vinylene-bridged hexaphyrin serves as an effective ligand that coordinates two zinc(II) ions using the central vinylene double bond in a 2-fashion along with the three pyrrolic nitrogen atoms.
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