While our ‘breaking and mending’ of porphyrin strategy proved versatile over the last decade in the generation of a range of pyrrole-modified porphyrins containing 4-, 5-, and 6-membered heterocycles, it failed to access systems incorporating larger rings. A reversal of the strategy – first mending, then breaking – now allowed the formation of a pyrrole-modified porphyrin containing an 8‑membered 1,3,6-triazocine-2,4,8-trione heterocycle. Mike Luciano and Wes Tardie continue working on the generalization of this strategy.

Luciano, M.; Tardie, W.; Zeller, M.; Brückner, C. ‘Supersizing Pyrrole-modified Porphyrins by Reversal of the ‘Breaking and Mending’ Strategy’ Chem. Commun. 2016, 52, 10133-10136.