Nucleophilic Thioglycosylation of Pentafluorophenyl-Substituted Porphyrinoids: Synthesis of Glycosylated Calix[n]phyrin and [28]Hexaphyrin Systems.

The use of carbohydrate thiolates for facile, high-yielding, regio- and stereoselective nucleophilic substitution reactions of complex pentafluorophenyl-substituted porphyrinoids is reported. The title reaction has successfully been applied to calix[4]phyrin, calix[6]phyrin, and [28]hexaphyrin substrates. The novel glycoporphyrinoid products with their extraordinary structures and unique photophysical properties are soluble in aqueous solutions and can serve as platforms for applications in biomedicine, catalysis, coordination, or redox chemistry.