Self-assembly in helical columnar mesophases and luminescence of chiral 1H-pyrazoles

Chiral polycatenar 1H-pyrazoles self-assemble to form columnar mesophases that are stable at room temperature. X-ray diffraction and CD studies in the mesophase indicate a supramolecular helical organization consisting of stacked H-bonded dimers. The liquid-crystalline compounds reported are 3,5-bis(dialkoxyphenyl)-1H-pyrazoles that incorporate two or four dihydrocitronellyl chiral tails. It can be observed that the grafting of these branched chiral substituents onto the 3,5-diphenyl-1H-pyrazole core has a beneficial role in inducing mesomorphism, because isomeric linear-chain compounds are not liquid crystalline; this is not the usual scheme of behavior. Furthermore, the molecular chirality is transferred to the columnar mesophase, because preferential helical arrangements are observed. Films of the compounds are luminescent at room temperature and constitute an example of the self-organization of nondiscoid units into columnar liquid-crystalline assemblies in which the functional molecular unit transfers its properties to a hierarchically built superstructure.