A non-catalytic condensation of Ni β-aminonorcorrole with aryl aldehydes is shown to produce a family of pyrromethane dimers that undergo deaminative cyclization to yield pyridine-fused bis(norcorrole)s comprising two antiaromatic macrocycles communicating by an aromatic moiety. The new compounds were characterized by spectroscopic, structural, and electrochemical methods supported by DFT calculations, all of which revealed unexpected antiaromaticity enhancement in the fused system.
The antiaromatic ring of norcorrole, a contracted tetrapyrrolic porphyrinoid, was subjected to [2+3] dipolar cycloaddition of iminonitriles. The paratropic character of the resulting chiral chlorins was retained. The chlorins were easily dehydrogenated in the presence of air, yielding pyrazole-fused norcorroles with markedly enhanced paratropicity.
An on-catalytic condensation of Ni II b-aminonorcorrole with aryl aldehydes is shown to produce af amily of pyrromethane dimers that undergo deaminative cyclization to yield pyridine-fused bis(norcorrole)s comprising two antiaromatic macrocycles communicating by an aromatic moiety. The new compounds were characterized by spectroscopic, structural, and electrochemical methods supported by DFT calculations,a ll of which revealed unexpected antiaromaticity enhancement in the fused system.
In recent years, norcorrole has attracted extensive attention of scientific researchers, owing to its distinct paratropic ring current, high single molecule conductivity, narrow HOMO-LUMO gap, stable redox performance and unique chemical reactivity. The different synthetic methods of norcorrole in recent years are reviewed, with emphasis on the derivatization reactions in four aspects: insertion, substitution, redox and extension of π conjugated system, and the development of norcorrole is prospected.
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