Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 27, Pages 7797-7800Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511883
Keywords
aromaticity; conjugation; electron transfer; macrocycles; porphyrinoids
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Funding
- IISER Pune
- SERB, Department of Science and Technology New Delhi, India
- CSIR, New Delhi, India
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Partial core-modification of a porphyrin can be employed to synthesize the 20 pi antiaromatic isophlorin. Unlike the tetra-, tri-, and dipyrrole derivatives of a porphyrin, a monopyrrole porphyrin exhibits antiaromatic characteristics. It undergoes a two-electron reversible ring oxidation to yield the 18 pi aromatic dication. H-1 NMR analysis provides distinct evidence of the altered electronic characteristics through typical paratropic and diatropic ring current effects for the 4n and the (4n + 2) pi-electron systems, respectively.
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