Abstract
Partial core-modification of a porphyrin can be employed to synthesize the 20π 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 18π aromatic dication.1H 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) π-electron systems, respectively.
Original language | English |
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Pages (from-to) | 7797-7800 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 27 |
DOIs | |
State | Published - 27 Jun 2016 |
Externally published | Yes |
Keywords
- aromaticity
- conjugation
- electron transfer
- macrocycles
- porphyrinoids
ASJC Scopus subject areas
- Catalysis
- General Chemistry