Catechol-based macrocyclic aromatic ether-sulfones: synthesis, characterization and ring-opening polymerization

Cyclocondensation between 4,4`-bis(4-chlorobenzenesulfonyl)biphenyl and catechol, with subsequent chromatographic separation of the reaction products, led to isolation four novel ether-sulfone macrocycles (cyclic dimer, -trimer, -tetramer -pentamer). Similarly, cyclocondensation catechol a seven-ring diketone/disulfone monomer allowed two new aromatic ether-ketone-sulfone macrocycles, cyclic dimer. Transannular shielding deshielding effects in produce substantial chemical shift differences for chemically equivalent protons 1H NMR spectra -dimer. Fluoride-initiated ring-opening polymerization trimer affords novel, high-molecular weight poly(ether-sulfone).