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Materials 2017, 10(7), 802; doi:10.3390/ma10070802

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

1
Dipartimento di Scienza dei Materiali, Università degli Studi di Milano Bicocca, via Cozzi 55, 20125 Milano, Italy
2
Dipartimento di Ingegneria Enzo Ferrari, Università degli Studi di Modena e Reggio Emilia, via Vivarelli 10, 41125 Modena, Italy
*
Author to whom correspondence should be addressed.
Received: 15 June 2017 / Revised: 11 July 2017 / Accepted: 11 July 2017 / Published: 15 July 2017
(This article belongs to the Special Issue Organic Electrochromic Materials)
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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 π 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-methylisoquinolinium-1-yl)-vinyl)-1,2,3,4-tetrahydroacri-dinium trifluoromethanesulfonate derivative shows the most interesting properties as an electrochromophore. View Full-Text
Keywords: organic electrochromic materials; violenes; quinoline; isoquinoline organic electrochromic materials; violenes; quinoline; isoquinoline
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Sassi, M.; Salamone, M.M.; Beverina, L.; Longoni, G.; Fontanesi, C.; Vanossi, D.; Cigarini, L.; Ruffo, R. An Integrated Theoretical/Experimental Study of Quinolinic–Isoquinolinic Derivatives Acting as Reversible Electrochromes. Materials 2017, 10, 802.

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