Synthesis, structure and complexation of biscrown-containing 1,4-distyrylbenzenes

Abstract

An improved method for the synthesis of two symmetric biscrown-containing and one model tetramethoxy-substituted 1,4-distyrylbenzenes was suggested. The structures of compounds were established by ¹H and ¹³C NMR spectroscopy and X-ray diffraction analysis. Spectrophotometric and fluorescent titration were used to determine spectral properties, stoichiometry, and stability of complexes of biscrown-containing 1,4-distyrylbenzenes with alkali and alkaline-earth metal cations. The stability of the complexes was found to depend on the metal cation size and charge, as well as on the size of the crown ether fragment. The electrochemical oxidation and reduction potentials of the biscrown-containing 1,4-distyrylbenzenes and the model compound in solution were determined and their basic differences from the corresponding characteristics of biscrown-containing stilbenes were identified.