Non-covalent bridging of bithiophenes through chalcogen bonding grips

In this work, chalcogen functionalized dithiophenes, equipped on both extremities with chalcogen-bonding recognition heterocycles, have been prepared following two synthetic pathways. The insertion of the chalcogenazolo[5,4-beta]pyridine allows the control of the organization at the solid state. X-Ray diffraction analysis of the single crystals, showed that the Te-doped derivatives give the most persistant assemblies, with the molecules arranging at solid-state in wire-like polymeric structures through TeMIDLINE HORIZONTAL ELLIPSISN interactions. As expected, the introduction of the Se and Te atoms, dramatically decreases the emission properties, with the Te-bearing congeners being virtually non emissive.