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Issue 19, 2018
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Push–pull quinoidal porphyrins

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A family of push–pull quinoidal porphyrin monomers has been prepared from a meso-formyl porphyrin by bromination, thioacetal formation, palladium-catalyzed coupling with malononitrile and oxidation with DDQ. Attempts at extending this synthesis to a push–pull quinoidal/cumulenic porphyrin dimer were not successful. The crystal structures of the quinoidal porphyrins indicate that there is no significant contribution from singlet biradical or zwitterionic resonance forms. The crystal structure of an ethyne-linked porphyrin dimer shows that the torsion angle between the porphyrin units is only about 3°, in keeping with crystallographic results on related compounds, but contrasting with the torsion angle of about 35° predicted by computational studies. The free-base quinoidal porphyrin monomers form tightly π-stacked layer structures, despite their curved geometries and bulky aryl substituents.

Graphical abstract: Push–pull quinoidal porphyrins

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The article was received on 26 Feb 2018, accepted on 24 Apr 2018 and first published on 24 Apr 2018

Article type: Paper
DOI: 10.1039/C8OB00491A
Citation: Org. Biomol. Chem., 2018,16, 3648-3654
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    Push–pull quinoidal porphyrins

    M. J. Smith, I. M. Blake, W. Clegg and H. L. Anderson, Org. Biomol. Chem., 2018, 16, 3648
    DOI: 10.1039/C8OB00491A

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