Constructing a dual-mode photochromic and intrinsically electrochromic device based on organic salts prepared by acid-base neutralization of pyromellitic diimides bearing a carboxyl group with aliphatic amines

[Display omitted] •Dual photo-electrochromic salts were prepared from acidic pyromellitic diimides and butylamine in polar organic solvent.•Amine induced single electron transfer was proposed as plausible mechanism based on theoretical and experimental investigations.•Dual photochromic and electroch...

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Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2020-02, Vol.388, p.112162, Article 112162
Main Authors: Abdinejad, Taleb, Zamanloo, Mohammad R., Esrafili, Mehdi D., Seifzadeh, Davod
Format: Article
Language:English
Subjects:
Electrochromism
Photochromism
Pyromellitic diimide
Radical anion
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Summary:[Display omitted] •Dual photo-electrochromic salts were prepared from acidic pyromellitic diimides and butylamine in polar organic solvent.•Amine induced single electron transfer was proposed as plausible mechanism based on theoretical and experimental investigations.•Dual photochromic and electrochromic device was constructed using the prepared salts. In this research, the reaction of pyromellitic diimides bearing acidic functional group(s) in the side chain with aliphatic amines was found to produce organic salts with excellent photochromic properties in polar organic solvents like dimethylformamide. Upon exposure to sunlight, the solution color changed from pale-yellow to green, showing the characteristics of pyromellitic diimide radical-anion. The study of photo-coloration mechanism using experimental and theoretical methods revealed that the acid-base reaction of the mentioned pyromellitic diimides with an aliphatic amine causes unequal increases in the HOMO and LUMO energy levels. Larger enhancement in the HOMO compared to the LUMO energy level resulted in a decrease of HOMO-LUMO energy gap. Under this condition, leading to a facilitated intramolecular electron transfer, the light-induced single electron transfer from the side chain to diimide carbonyl group produced a green radical-anion. The prepared salts could be considered as intrinsic electrochromic materials besides possessing the photochromic behavior owing to their good electrical conductivity and electrochromic properties.
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2019.112162