Porphyriynes: 18-π-Conjugated Macrocycles Incorporating a Triple Bond

Tetraphenylporphyriyne (Pynel), a novel porphyrin analogue with a C C bond incorporated into an 18-pi-conjugated system, has been created via cleavage of the N-confused pyrrolic ring in Ag(III) N-confused tetraphenylporphyrin. The structure of Pynel was confirmed by X-ray crystallography and H-1 NMR, IR, and UV-vis spectroscopy. The mechanism of cleavage of the N-confused pyrrolic ring was investigated by theoretical calculations. The successful synthesis of other Pynes indicated the generality of this protocol.

Automated summary

A novel porphyrin analogue with a C C bond incorporated into an 18-pi-conjugated system, named Tetraphenylporphyriyne (Pynel), has been synthesized via cleavage of the N-confused pyrrolic ring in Ag(III) N-confused tetraphenylporphyrin. The structure of Pynel was confirmed using various spectroscopic techniques, and the mechanism of the cleavage process was investigated using theoretical calculations. The successful synthesis of other Pynes demonstrated the generality of this methodology.