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Issue 21, 2018
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Aromaticity control via modifications of a macrocyclic frame: 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrin

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Abstract

The incorporation of a 9,10-dimethoxyphenanthrene moiety into a porphyrin framework results in the formation of a hybrid macrocycle – 5,6-dimethoxyphenanthriporphyrin 1, fusing the structural features of polycyclic aromatic hydrocarbons and porphyrins. Simple transformations of antiaromatic 1 led to two macrocycles incorporating phenanthrene and phenanthrenequinone units: isophenanthriporphyrin and 5,6-dioxophenanthriporphyrin. The reversible protonation of 1 at the central meso-carbon atom stabilizes its constitutional isomer, i.e. the Cs-symmetric isophenanthriporphyrin in its dicationic form 1-A-H22+. The addition of an acid to nonaromatic 5,6-dioxophenanthriporphyrin 2 yielded the aromatic tricationic form protonated at the carbonyl oxygen atoms. In the presence of tetrafluoroboric acid, etherate, 2 underwent borylation at carbonyl oxygen atoms forming the aromatic BF2-derivative.

Graphical abstract: Aromaticity control via modifications of a macrocyclic frame: 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrin

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Publication details

The article was received on 23 Jul 2018, accepted on 19 Aug 2018 and first published on 20 Aug 2018


Article type: Research Article
DOI: 10.1039/C8QO00751A
Citation: Org. Chem. Front., 2018,5, 3068-3076
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    Aromaticity control via modifications of a macrocyclic frame: 5,6-dimethoxyphenanthriporphyrin and 5,6-dioxophenanthriporphyrin

    K. Kupietz, M. J. Białek, A. Białońska, B. Szyszko and L. Latos-Grażyński, Org. Chem. Front., 2018, 5, 3068
    DOI: 10.1039/C8QO00751A

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