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Short-Chained Anthracene Strapped Porphyrins and Their Endoperoxides

submitted on 04.03.2020, 19:11 and posted on 05.03.2020, 11:24 by Susan Callaghan, Keith Flanagan, John E. O'Brien, Mathias Senge
The synthesis of short-chained anthracene-strapped porphyrins and their Zn(II)complexes are reported. The key synthetic step employed was a [2+2] condensation between a dipyrromethane and 2,2'-((anthracene-9,10-diylbis(methylene))bis(oxy))dibenzaldehyde. Following exposure to polychromatic light, self-sensitized singlet oxygen and the anthracene moieties underwent [4+2] cycloaddition reactions to yield the corresponding endoperoxides. 1H NMR studies demonstrate that the endoperoxide readily formed in chloroform-d and decayed at 85 °C. X-ray crystallography and absorption spectroscopy were used to confirm macrocyclic distortion in the parent strapped porphyrins and endoperoxides. Additionally, X-ray crystallography indicated that endoperoxide formation occurred exclusively on the outside face of the anthracene moiety.


Science Foundation Ireland (IvP 13/IA/1894)

Irish Research Council (GOIPG/2016/1250)

Technische Universität München (August-Wilhelm Scheer visiting professorship)


Email Address of Submitting Author


Trinity College Dublin, The University of Dublin



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0


Read the published paper

in European Journal of Organic Chemistry

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