Use of Ag(II) as a removable template in porphyrin chemistry: diol cleavage products of [meso-tetraphenyl-2,3-cis-diolchlorinato]silver(II)

The use of AgII as a removable template in synthetic porphyrin chemistry is described. Mild procedures for the insertion of AgII into chlorins and the demetallation of the [chlorinato]AgII complexes are delineated. The UV–vis spectra of the novel [chlorinato]AgII complexes are discussed. The diol cleavage products of [meso-tetraphenyl-2,3-diolchlorinato]silver(II) under a number of conditions are characterized and compared to those resulting from the cleavage of the corresponding free base diol chlorin or its NiII complex, highlighting the unique templating effect of AgII. The scopes and limits of electrospray ionization mass spectrometry (ESI-MS) for the analysis of AgII chlorins is described. The use of AgII as a templating metal is superior over NiII or ZnII for the preparation of free base pyrrole-modified porphyrins along metal templated pathways.