Substituent-Controlled Tailoring of Chalcogen-Bonded Supramolecular Nanoribbons in the Solid State

[Image: see text] In this work, we design and synthesize supramolecular 2,5-substituted chalcogenazolo[5,4-β]pyridine (CGP) synthons arranging in supramolecular ribbons at the solid state. A careful choice of the combination of substituents at the 2- and 5-positions on the CGP scaffold is outlined to accomplish supramolecular materials by means of multiple hybrid interactions, comprising both chalcogen and hydrogen bonds. Depending on the steric and electronic properties of the substituents, different solid-state arrangements have been achieved. Among the different moieties on the 5-position, an oxazole unit has been incorporated on the Se- and Te-congeners by Pd-catalyzed cross-coupling reaction and a supramolecular ribbon-like organization was consistently obtained at the solid state.