Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are thiols tolerated in the self-assembly process?

Three novel thiol bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, Bronsted acid catalysis, and disulfide chemistry. One new thiosubstituted macrocycle stands out in particular, as it forms a hexameric capsule in CDCl3 capable of terpene cyclizations, dimerizes via disulfide bridges under mild oxidative conditions, and most importantly shows guest uptake of both alkyl ammonium salts and C60-fullerenes.