A series of compounds, featuring an ethenylic bridge and quinoline and isoquinoline end capping units possessing systematically varied substitution patterns, were prepared as molecular materials for electrochromic applications. The different structures were optimized in order to maximize the electrochromic contrast in the visible region, mostly by achieving a completely UV-absorbing oxidized state. Density functional theory (DFT) calculations are exploited in order to rationalize the correlation between the molecular structure, the functional groups' electronic properties, and the electrochemical behavior. It is shown that the molecular planarity (i.e. ring/ring pi conjugation) plays a major role in defining the mechanism of the electrochemical charge transfer reaction, while the substituent's nature has an influence on the LUMO energy. Among the compounds here studied, the (E)-10-methyl-9-(2-(2-methylisoquinolinium1- yl)-vinyl)-1,2,3,4-tetrahydroacri-dinium trifluoromethanesulfonate derivative shows the most interesting properties as an electrochromophore.

An Integrated Theoretical/Experimental Study of Quinolinic-Isoquinolinic Derivatives Acting as Reversible Electrochromes / Sassi, Mauro; Salamone, Matteo M; Beverina, Luca; Longoni, Gianluca; Fontanesi, Claudio; Vanossi, Davide; Cigarini, Luigi; Ruffo, Riccardo. - In: MATERIALS. - ISSN 1996-1944. - 10:7(2017), pp. 802-815. [10.3390/ma10070802]

An Integrated Theoretical/Experimental Study of Quinolinic-Isoquinolinic Derivatives Acting as Reversible Electrochromes

Beverina, Luca;Fontanesi, Claudio;Vanossi, Davide;Cigarini, Luigi;
2017

Abstract

A series of compounds, featuring an ethenylic bridge and quinoline and isoquinoline end capping units possessing systematically varied substitution patterns, were prepared as molecular materials for electrochromic applications. The different structures were optimized in order to maximize the electrochromic contrast in the visible region, mostly by achieving a completely UV-absorbing oxidized state. Density functional theory (DFT) calculations are exploited in order to rationalize the correlation between the molecular structure, the functional groups' electronic properties, and the electrochemical behavior. It is shown that the molecular planarity (i.e. ring/ring pi conjugation) plays a major role in defining the mechanism of the electrochemical charge transfer reaction, while the substituent's nature has an influence on the LUMO energy. Among the compounds here studied, the (E)-10-methyl-9-(2-(2-methylisoquinolinium1- yl)-vinyl)-1,2,3,4-tetrahydroacri-dinium trifluoromethanesulfonate derivative shows the most interesting properties as an electrochromophore.
2017
10
7
802
815
An Integrated Theoretical/Experimental Study of Quinolinic-Isoquinolinic Derivatives Acting as Reversible Electrochromes / Sassi, Mauro; Salamone, Matteo M; Beverina, Luca; Longoni, Gianluca; Fontanesi, Claudio; Vanossi, Davide; Cigarini, Luigi; Ruffo, Riccardo. - In: MATERIALS. - ISSN 1996-1944. - 10:7(2017), pp. 802-815. [10.3390/ma10070802]
Sassi, Mauro; Salamone, Matteo M; Beverina, Luca; Longoni, Gianluca; Fontanesi, Claudio; Vanossi, Davide; Cigarini, Luigi; Ruffo, Riccardo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1159473
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