Ion-based materials derived from positively and negatively charged chloride complexes of π-conjugated molecules

Oriented salts from planar charged species were prepared by combining positively and negatively charged receptor-anion complexes with similar geometries using dicationic and electronically neutral π-conjugated receptors. Phenylene-or pyrimidine-bridged bis(imidazolium) dicationic anion receptors formed monocationic receptor-Cl^- complexes that were accompanied by a free Cl^-. This free Cl^- was subsequently captured by pyrrole-based neutral anion receptors to form negatively charged receptor-Cl^- complexes. The ion pair of the resulting positively and negatively charged planar receptor-Cl^- complexes could produce a supramolecular octane gel, adopting a lamellar self-organized structure in its xerogel state. On the other hand, the solid-state ion pairs had hexagonal columnar mesophases, which formed via alternate stacking of the positively and negatively charged planar receptor-Cl^- complexes. By use of the flash-photolysis time-resolved microwave conductivity technique, the one-dimensional charge-carrier transporting property, with a mobility of 0.05 cm² V^-1 s^-1, was determined for the newly prepared solid-state ion pairs.