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 selected 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 rationalized 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. - ELETTRONICO. - 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;Passaponti Maurizio;Giurlani Walter;
2020

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 selected 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 rationalized on the basis of theoretical values of optical rotation (OR), calculated at the CAMB3LYP/6-31G(d,p) level of the theory.
2020
856
113705
113705
Innocenti Massimo; Passaponti Maurizio; Giurlani Walter; Giacomino Agnese; Pasquali Luca; Giovanardi Roberto; Fontanesi Claudio
File in questo prodotto:
Non ci sono file associati a questo prodotto.

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

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1182016
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 9
social impact