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Short-Chained Anthracene Strapped Porphyrins and Their Endoperoxides

preprint
submitted on 04.03.2020 and posted on 05.03.2020 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.

Funding

Science Foundation Ireland (IvP 13/IA/1894)

Irish Research Council (GOIPG/2016/1250)

Technische Universität München (August-Wilhelm Scheer visiting professorship)

History

Email Address of Submitting Author

sengem@tcd.ie

Institution

Trinity College Dublin, The University of Dublin

Country

Ireland

ORCID For Submitting Author

0000-0002-7467-1654

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0

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in European Journal of Organic Chemistry

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