Influencing prototropy by metal ion coordination: supramolecular transformation of a dynamer into a Zn-based toroidal species

Publish Year: 2021
Publisher:  Journal of Materials Chemistry C, 2021, 9
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M. Čonková, W. Drożdż, Z. Miłosz, P. Cecot, J. Harrowfield, M. Lewandowski, A. R. Stefankiewicz
Disruption of a tautomeric equilibrium by coordination self-assembly depends upon a delicate interplay between supramolecular interactions but has not been studied for supramolecular polymers in two dimensions at the solid–liquid interface. Presented herein is the description of a functionalized molecular module which in DMSO solution generates a highly compact dynamic aggregate in its lactam (amide) form that undergoes reaction with Zn(II) ion to give a ML2-type complex in which one lactam unit on each ligand has been converted to its iminol form, enabling bidentate binding also involving pyrimidine-N. These solution measurements, as well as a study by scanning tunneling microscopy at the liquid/graphite interface, corroborated by density functional studies, have revealed how the tautomeric equilibrium can be modulated by the addition of a metal salt.

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