On-Surface Molecular Recognition Driven by Chalcogen Bonding

Result of the Month

Author: L. Camilli, C. Hogan, D. Romito, L. Persichetti, A. Caporale, M.Palummo, M. Di Giovannantonio and D. Bonifazi Institute: ''University of Rome'' JACS Au
URL: https://doi.org/10.1021/jacsau.4c00325
Date: 10/2024 Instruments: INFINITY SPM Lab

Chalcogen bonding interactions have been widely employed to create ordered non-covalent assemblies in both solids and liquids. Yet, their ability to engineer molecular self-assembly on surfaces has not been demonstrated. Here, we report the first demonstration of on-surface molecular recognition solely governed by chalcogen bonding interaction. Scanning tunnelling microscopy and ab initio calculations reveal that a pyrenyl derivative can undergo non-covalent chiral dimerization on the Au(111) surface through double Ch∙∙∙N interactions involving Te- or Se-containing chalcogenazolo pyridine motifs. In contrast, reference chalcogenazole counterparts lacking the pyridyl moiety fail to form regular self-assemblies on Au, resulting in disordered assemblies.

In this paper, low-temperature scanning tunnelling microscopy images taken at constant height with a CO-functionalized tip are used to demonstrate the formation of supramolecular dimers stabilized by a pair of chalcogen bonding interactions in chalcogenazolo pyridine compounds self-assembled on metal surfaces. Moreover, charge density analysis computed within the framework of density functional calculations confirmed the attractive non-covalent nature of Ch∙∙∙N interaction when the dimers are assembled on Au(111). This study expands our comprehension of supramolecular interactions, while delving into the novel role of chalcogen bonding interactions in surface-based molecular recognition.

On-Surface Molecular Recognition Driven by Chalcogen Bonding

Result of the Month

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