Abstract
AbstractDoping, through oxidation or reduction, is often used to modify the properties of π‐conjugated oligomers. In most cases, the resulting charge distribution is difficult to determine. If the oligomer is cyclic and doping establishes global aromaticity or antiaromaticity, then it is certain that the charge is fully delocalized over the entire perimeter of the ring. Herein we show that reduction of a six‐porphyrin nanoring using decamethylcobaltocene results in global aromaticity (in the 6− state; [90 π]) and antiaromaticity (in the 4− state; [88 π]), consistent with the Hückel rules. Aromaticity is assigned by NMR spectroscopy and density‐functional theory calculations.
Highlights
Doping, through oxidation or reduction, is often used to modify the properties of p-conjugated oligomers
We show that reduction of a six-porphyrin nanoring using decamethylcobaltocene results in global aromaticity and antiaromaticity, consistent with the Hückel rules
Aromaticity is assigned by NMR spectroscopy and density-functional theory calculations
Summary
Through oxidation or reduction, is often used to modify the properties of p-conjugated oligomers. We show that reduction of a six-porphyrin nanoring using decamethylcobaltocene results in global aromaticity (in the 6À state; [90 p]) and antiaromaticity (in the 4À state; [88 p]), consistent with the Hückel rules. There are many macrocyclic p-conjugated rings with [4n + 2] or [4n] p-electrons that do not display global aromatic or antiaromatic ring currents.
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