Tuning carbonyl interactions in dibenzochalcogenophenes

Abstract

This study presents a series of functionalized dibenzochalcogenophenes (DBE; E: S, Se, Te) with a benzoyl moiety in the 3- and 4-position. Single crystal X-ray diffraction of all compounds was utilized to examine crystal packing and Hirshfeld analysis, focussing on chalcogen bonding. The data indicated an increasing number of chalcogen-driven contacts corresponding to the increasing size of the chalcogen within the structure, aligning with theoretical calculations and previous studies. For DBEs substituted with a benzoyl group at 4-position, conformational fixation could be induced by the carbonyl group, impeding the rotation of phenyl residues. Conversely, dibenzotellurophene with the benzoyl moiety in 3-position exhibited dimerization through chalcogen–carbonyl bonds based on its self-complementary structure, revealing a new interaction motif based on chalcogen bonding applicable for future use in supramolecular assembly.