Non-covalent bridging of bithiophenes through chalcogen bonding grips

D. Romito, N. Biot, F. Babudri and D. Bonifazi
New J. Chem.
, 2020,44, 6732-6738.
DOI: 10.1039/C9NJ06202E


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-β]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 Te⋯N 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.

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