Cocrystals and Salts of 3,5-Bis(pyridinylmethylene)piperidin-4-one with Aromatic Poly-Carboxylates and Resorcinols: Influence of Stacking Interactions on Solid-State Luminescence Properties

Abstract

Two bis-pyridyl-substituted α,β-unsaturated ketones were shown to form complexes with carboxylic acids and resorcinol derivatives. The neutral acid–acid homosynthon was observed in only one complex out of the five acid-bis-pyridyl containing complexes studied here, while the –COO−⋯HOOC– synthon was found to be dominant as it was observed in four complexes. The carboxylates self-assembled to form discrete dimeric, anionic, 1D chains and also exhibited mixed ionic hydrogen bonds. On the other hand, resorcinol derivatives displayed O–H⋯N hydrogen bonding to form tetrameric aggregates of bis-pyridyl ketone molecules and respective co-formers, while 3,5-dihydroxy benzoic acid (DHBA) molecules formed 1D chains by clipping two molecules of ketones with three DHBA molecules. Such clipping by the resorcinol derivatives promoted continuous π–π stacking interactions. Consequently, these materials emitted at higher wavelengths compared with the parent bis-pyridyl-substituted α,β-unsaturated ketones.