Working Paper
Authors
- Susan Callaghan ,
- Keith Flanagan ,
- John E. O'Brien ,
- Mathias O.. Senge
Trinity College Dublin, The University of Dublin
Abstract
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.
Version notes
Version 1.0
Content

Supplementary material

Strapped-Por 1O2 SI Chemrvix