Symmetry-Driven Formation of Chiral Boroxine-Based Organometallic Oligomers on Ag(001)

Formation par symétrie d'oligomères organométalliques chiraux à base de boroxine sur Ag(001)

Amelia Domínguez-Celorrio (1) , Manuel Vilas-Varela (2) , Diego Peña (2) , Véronique Langlais (3) , David Serrate (1)

1 University of Zaragoza - Universidad de Zaragoza [Zaragoza]
2 Centro Singular de Investigacion en Química Bioloxica e Materiais Moleculares [Santiago de Compostela, Spain]
3 CEMES - Centre d'élaboration de matériaux et d'études structurales

Two-dimensional molecular assemblies on surfaces have opened a way to design and control chirality, featuring promising electronic and chemical properties that depend on the local handedness of the layer. Yet, the mechanisms leading to spontaneous chiral resolution are not fully understood at every reaction stage. Here, starting from achiral 10-bromoanthracene-9-boronic acid as a molecular precursor, we demonstrate enantiomeric induction in products during the stage of covalent bonding, stemming from the competing point symmetries of the Ag(001)-supporting surface and the reaction products. Upon dehalogenation and dehydration of precursors, hexagonal boroxine rings linked by organometallic anthracene dimers are formed, which undergo a strong interaction with a fourfold symmetric substrate. The prochiral structural character of the resulting oligomer and its impact over the spatial distribution of the electronic molecular states are revealed by highresolution scanning tunneling microscopy and spectroscopy.

Domaines: Chimie-Physique [physics.chem-ph]

Amelia Domínguez-Celorrio, Manuel Vilas-Varela, Diego Peña, Véronique Langlais, David Serrate. Symmetry-Driven Formation of Chiral Boroxine-Based Organometallic Oligomers on Ag(001). Journal of Physical Chemistry C, 2021, 125 (3), pp.2015 - 2021. ⟨10.1021/acs.jpcc.0c08039⟩. ⟨hal-03396644⟩