Glassy carbon (GC) surfaces are functionalized exploiting the electrochemical reduction of asymmetric iodonium salts of the general formula [4-Zsingle bondC6H4single bondI+single bondCtriple bond; length of mdashC(CH2)4Cl, Z = NO2, Br, F, H, or CH3]. The range of Z groups was selected aiming to examine the Carylsingle bondI bond energy as a function of the “electron withdrawing/electron donating” ability of the Z-group, with the ultimate purpose of controlling the alkynyl/aryl grafting ratio. The electroreduction mechanism and the characteristics of the grafted surface are studied by means of cyclic voltammetry and X-ray photoelectron spectroscopy. It is shown that the alkynyl/aryl grafting ratio decreases with the increasing electron withdrawing nature of Z, which induces a weakening of the Carylsingle bondI bond. Ab initio DFT vertical electron affinities (EAv) allowed to rationalize the electroreduction potentials of both the bulk and surface functionalised redox couples. Moreover, the alkynyl/aryl grafting ratio is assessed, at a molecular level, on the basis of ab initio DFT potential energy surfaces.

Electrochemically assisted grafting of asymmetric alkynyl(aryl)iodonium salts on glassy carbon with focus on the alkynyl/aryl grafting ratio / Florini, Nicola; M., Michelazzi; Parenti, Francesca; Mucci, Adele; Sola, Marco; C., Baratti; De Renzi, Valentina; K., Daasbjerg; S. U., Pedersen; Fontanesi, Claudio. - In: JOURNAL OF ELECTROANALYTICAL CHEMISTRY. - ISSN 1572-6657. - STAMPA. - 710:(2013), pp. 41-47. [10.1016/j.jelechem.2013.01.023]

Electrochemically assisted grafting of asymmetric alkynyl(aryl)iodonium salts on glassy carbon with focus on the alkynyl/aryl grafting ratio

FLORINI, Nicola;PARENTI, Francesca;MUCCI, Adele;SOLA, Marco;DE RENZI, Valentina;FONTANESI, Claudio
2013

Abstract

Glassy carbon (GC) surfaces are functionalized exploiting the electrochemical reduction of asymmetric iodonium salts of the general formula [4-Zsingle bondC6H4single bondI+single bondCtriple bond; length of mdashC(CH2)4Cl, Z = NO2, Br, F, H, or CH3]. The range of Z groups was selected aiming to examine the Carylsingle bondI bond energy as a function of the “electron withdrawing/electron donating” ability of the Z-group, with the ultimate purpose of controlling the alkynyl/aryl grafting ratio. The electroreduction mechanism and the characteristics of the grafted surface are studied by means of cyclic voltammetry and X-ray photoelectron spectroscopy. It is shown that the alkynyl/aryl grafting ratio decreases with the increasing electron withdrawing nature of Z, which induces a weakening of the Carylsingle bondI bond. Ab initio DFT vertical electron affinities (EAv) allowed to rationalize the electroreduction potentials of both the bulk and surface functionalised redox couples. Moreover, the alkynyl/aryl grafting ratio is assessed, at a molecular level, on the basis of ab initio DFT potential energy surfaces.
2013
710
41
47
Electrochemically assisted grafting of asymmetric alkynyl(aryl)iodonium salts on glassy carbon with focus on the alkynyl/aryl grafting ratio / Florini, Nicola; M., Michelazzi; Parenti, Francesca; Mucci, Adele; Sola, Marco; C., Baratti; De Renzi, Valentina; K., Daasbjerg; S. U., Pedersen; Fontanesi, Claudio. - In: JOURNAL OF ELECTROANALYTICAL CHEMISTRY. - ISSN 1572-6657. - STAMPA. - 710:(2013), pp. 41-47. [10.1016/j.jelechem.2013.01.023]
Florini, Nicola; M., Michelazzi; Parenti, Francesca; Mucci, Adele; Sola, Marco; C., Baratti; De Renzi, Valentina; K., Daasbjerg; S. U., Pedersen; Font...espandi
File in questo prodotto:
File Dimensione Formato  
JEC201341-47.pdf

Accesso riservato

Tipologia: Versione pubblicata dall'editore
Dimensione 524.21 kB
Formato Adobe PDF
524.21 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/11380/982673
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 8
  • ???jsp.display-item.citation.isi??? 8
social impact