On-Surface Molecular Recognition Driven by Chalcogen Bonding

Luca Camilli; Conor Hogan; Deborah Romito; Luca Persichetti; Antonio Caporale; Maurizia Palummo; Marco Di Giovannantonio; Davide Bonifazi

doi:10.1021/jacsau.4c00325

Titel

On-Surface Molecular Recognition Driven by Chalcogen Bonding

Autor*in

Luca Camilli

Department of Physics, University of Rome “Tor Vergata”

Conor Hogan

Department of Physics, University of Rome “Tor Vergata”

Deborah Romito

Institut für Organische Chemie, Fakultät für Chemie, Universität Wien

... show all

Abstract

Chalcogen bonding interactions (ChBIs) have been widely employed to create ordered noncovalent assemblies in 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 ChBIs. Scanning tunneling microscopy and ab initio calculations reveal that a pyrenyl derivative can undergo noncovalent 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.

Stichwort

chalcogenazoleschalcogen bondssurface self-assemblysupramolecular chemistryscanning tunneling microscopydensity functional theoryab initio calculations

Objekt-Typ

journal article

Sprache

Englisch [eng]

Persistent identifier

phaidra.univie.ac.at/o:2086391

DOI

10.1021/jacsau.4c00325

Erschienen in

Titel

JACS Au

Band