Novel supramolecular charge-transfer systems based on bis(18-crown-6)stilbene and viologen analogues bearing two ammonioalkyl groups

Abstract

A series of new viologen analogues bearing two ammonioalkyl groups (2–4) were synthesized in order to study their complexation with bis(18-crown-6)stilbene (1b). Electronic spectroscopy and 1H NMR measurements show that in acetonitrile, bis(crown) stilbene 1b forms highly stable 1 : 1 and 2 : 1 charge-transfer (CT) complexes with π-acceptors 2–4 owing to host–guest bonding. The influence of geometric and electronic factors on the complex formation constants are discussed. The structures of the supramolecular CT complexes are analyzed on the basis of 1H and 13C NMR data obtained in solution and in the solid state. X-Ray diffraction data for 1b and for model tetramethoxystilbene are also reported.