Engineering Te‐Containing Recognition Modules for Chalcogen Bonding: Towards Supramolecular Polymeric Materials

Abstract

Aiming at the preparation of one-dimensional (1D) chalcogen-bonded supramolecular polymers at the solid state, this work describes the different syntheses which have been challenged to obtain ditopic molecular modules. At first, tellurazolopyridyl (TZP) rings have been chosen as recognition units, given their well-proven ability and persistency to self-assemble through double Te•••N chalcogen bonds (ChBs). The second synthetic strategy dealt with the preparation of pyridyl-modified ebselen Te-containing analogues. By attempting several synthetic protocols, the targeted ebselen derivatives could not be obtained, whereas an unexpected Tecontaining lactone as well as a spiro-type Te(IV)-containing derivatives were isolated, with the latter investigated by X-ray diffraction (XRD) analysis.

On-Surface Molecular Recognition Driven by Chalcogen Bonding

“…If one excludes the use of cationic heterocycles, one can note that outside a crystalline environment, the formation of such dimers is unprecedented. Indeed, even in solution, conclusive data demonstrating such self-assembly of neutral heterocycles have yet to be reported thus far. , Building on earlier studies at the solid state, in which we have shown that chalcogenazolo pyridine (CGP) moieties persistently undergo self-assembly into dimers through double Ch···N interactions, − we conjectured that the Se- and Te-bearing CGP motifs could also be exploited to govern molecular assemblies on surfaces (Figure e) . With this aim, we designed and prepared pyrene-based CGP modules that could undergo dimerization through ChB-driven molecular recognition.…”