In the last decade, hydrogen (H-)tautomerization, that is, a reaction that involves simple intramolecular proton transfer, has been studied in single phthalocyanine, porphyrin, and porphycene derivatives as a prototypical single molecular conductance switch. Here, by means of low-temperature scanning tunneling microscopy and density functional theory calculations, we report a binary H-tautomerism and stereoisomeric conformational switch in (amino-functionalized) porphyrins assembled in molecular chains on a gold surface. We show that the formation of the chain is crucial for the binary tautomeric switch mechanism as the single molecule switches differently. Our findings suggest that the (amino-)functionalization of molecules can be exploited not only to drive the formation of molecular self-assemblies but also to steer their switching properties.

Binary Conformational Switches in a Porphyrin Chain: Tautomerization and Stereoisomerization

Feng, Zhijing;Velari, Simone;Dri, Carlo;Peressi, Maria
;
Comelli, Giovanni
2020-01-01

Abstract

In the last decade, hydrogen (H-)tautomerization, that is, a reaction that involves simple intramolecular proton transfer, has been studied in single phthalocyanine, porphyrin, and porphycene derivatives as a prototypical single molecular conductance switch. Here, by means of low-temperature scanning tunneling microscopy and density functional theory calculations, we report a binary H-tautomerism and stereoisomeric conformational switch in (amino-functionalized) porphyrins assembled in molecular chains on a gold surface. We show that the formation of the chain is crucial for the binary tautomeric switch mechanism as the single molecule switches differently. Our findings suggest that the (amino-)functionalization of molecules can be exploited not only to drive the formation of molecular self-assemblies but also to steer their switching properties.
Pubblicato
https://pubs.acs.org/doi/10.1021/acs.jpcc.0c00471
File in questo prodotto:
File Dimensione Formato  
jp-2020-00471m.R1_Proof_hi_lowres.pdf

Open Access dal 07/05/2021

Descrizione: Articolo principale
Tipologia: Bozza finale post-referaggio (post-print)
Licenza: Digital Rights Management non definito
Dimensione 434.89 kB
Formato Adobe PDF
434.89 kB Adobe PDF Visualizza/Apri
acs.jpcc.0c00471.pdf

Accesso chiuso

Descrizione: Articolo principale
Tipologia: Documento in Versione Editoriale
Licenza: Digital Rights Management non definito
Dimensione 5.17 MB
Formato Adobe PDF
5.17 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
jp0c00471_si_001.pdf

accesso aperto

Descrizione: Supporting Information The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpcc.0c00471.
Tipologia: Altro materiale allegato
Licenza: Copyright Editore
Dimensione 7.72 MB
Formato Adobe PDF
7.72 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/2966586
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 2
  • ???jsp.display-item.citation.isi??? 2
social impact