The efficiency of charge transmission in chiral compared to achiral molecular systems, of structurally related compounds, is probed via cyclic voltammetry measurements. For such a purpose five different thiols have been selected two achiral (i.e. 3-mercaptopropionic acid (MPA) and 8-mercapto-1-octanol (M8O)) and three chiral (i.e. L- and D-cysteine (Lcys, Dcys) and D-penicillamine (Dpen)). These compounds are used to form 2D self-assembled monolayers (SAM) on gold. Cyclic voltammetry (CV) measurements, by using the potassium hexacyanoferrate(III)/potassium hexacyanoferrate(II) redox couple (Fe3Fe2), are exploited to probe the charge transfer ability of the electrode|SAM|solution interface. In particular, MPA, Lcys and Dpen compounds are se- lected due to their quite similar structural and geometrical characteristics (virtually the same molecular length and terminal groups). M8O is a longer SAM forming thiol, which was selected as a reference blocking electrode compound. The comparison of the cyclic voltammetry data shows that a better ability in the charge transmission is obtained when chiral SAM are used; namely in the case of L-cysteine and D-penicillamine. This result can be related to the spin filtering ability of chiral compounds: chiral induced spin selectivity (CISS) effect. As rational- ized on the basis of theoretical values of optical rotation (OR), calculated at the CAMB3LYP/6-31G(d,p) level of the theory.

Spin dependent electrochemistry: Focus on chiral vs achiral charge transmission through 2D SAMs adsorbed on gold / Innocenti, Massimo; Passaponti, Maurizio; Giurlani, Walter; Giacomino, Agnese; Pasquali, Luca; Giovanardi, Roberto; Fontanesi, Claudio. - In: JOURNAL OF ELECTROANALYTICAL CHEMISTRY. - ISSN 1572-6657. - 856:(2020), pp. 113705-113705. [10.1016/j.jelechem.2019.113705]

Spin dependent electrochemistry: Focus on chiral vs achiral charge transmission through 2D SAMs adsorbed on gold

Innocenti, Massimo;Pasquali, Luca;Giovanardi, Roberto;Fontanesi, Claudio
2020-01-01

Abstract

The efficiency of charge transmission in chiral compared to achiral molecular systems, of structurally related compounds, is probed via cyclic voltammetry measurements. For such a purpose five different thiols have been selected two achiral (i.e. 3-mercaptopropionic acid (MPA) and 8-mercapto-1-octanol (M8O)) and three chiral (i.e. L- and D-cysteine (Lcys, Dcys) and D-penicillamine (Dpen)). These compounds are used to form 2D self-assembled monolayers (SAM) on gold. Cyclic voltammetry (CV) measurements, by using the potassium hexacyanoferrate(III)/potassium hexacyanoferrate(II) redox couple (Fe3Fe2), are exploited to probe the charge transfer ability of the electrode|SAM|solution interface. In particular, MPA, Lcys and Dpen compounds are se- lected due to their quite similar structural and geometrical characteristics (virtually the same molecular length and terminal groups). M8O is a longer SAM forming thiol, which was selected as a reference blocking electrode compound. The comparison of the cyclic voltammetry data shows that a better ability in the charge transmission is obtained when chiral SAM are used; namely in the case of L-cysteine and D-penicillamine. This result can be related to the spin filtering ability of chiral compounds: chiral induced spin selectivity (CISS) effect. As rational- ized on the basis of theoretical values of optical rotation (OR), calculated at the CAMB3LYP/6-31G(d,p) level of the theory.
2020
29-nov-2019
856
113705
113705
Spin dependent electrochemistry: Focus on chiral vs achiral charge transmission through 2D SAMs adsorbed on gold / Innocenti, Massimo; Passaponti, Maurizio; Giurlani, Walter; Giacomino, Agnese; Pasquali, Luca; Giovanardi, Roberto; Fontanesi, Claudio. - In: JOURNAL OF ELECTROANALYTICAL CHEMISTRY. - ISSN 1572-6657. - 856:(2020), pp. 113705-113705. [10.1016/j.jelechem.2019.113705]
Innocenti, Massimo; Passaponti, Maurizio; Giurlani, Walter; Giacomino, Agnese; Pasquali, Luca; Giovanardi, Roberto; Fontanesi, Claudio
File in questo prodotto:
File Dimensione Formato  
Fontanesi_JElectrochem2020.pdf

Accesso riservato

Descrizione: Articolo principale
Tipologia: Versione pubblicata dall'editore
Dimensione 681.31 kB
Formato Adobe PDF
681.31 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1185569
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 6
  • ???jsp.display-item.citation.isi??? 6
social impact