Kikot L. Molecular clips based on the diphenylglycoluril and benzo(dibenzo)crown ethers: synthesis, structure, properties

There were tested several methods for obtaining the molecular clips, and alternative method, based on the interaction of diphenylglycoluril bisether with benzocrown ethers in polyphosphoric acid under the Chernyak-Einhorn reaction conditions was proposed. The formation of products of 4,5-disubstitution at the benzene ring of crown ethers was proved. For the synthesis of molecular clips based on dibenzocrown ethers, bromine atoms were introduced into one of benzene rings of initial dibenzocrown ethers as protective groups. These atoms after reaction with the diphenylglycoluril bisether in polyphosphoric acid were removed with hydrogen in the presence of Pd/C and Et3N. The complexation of obtained molecular clips with cations of alkali metals, salts of aliphatic diamines and salts of substituted 4,4'-bipyridinium was studied. A comparison of the composition and structure of the complexes in solution and in crystalline state was carried out.