Heterophenoquinones: Tuning Optoelectronics and Electrochromicity.
Chemistry
; 29(37): e202203862, 2023 Jul 03.
Article
em En
| MEDLINE
| ID: mdl-36789644
ABSTRACT
We report the synthesis and optoelectronic properties of 16 thiophene-based heterophenoquinones. These compounds were accessed in a convergent and modular approach, allowing for their efficient synthesis. Tuning of the optical band gap was achieved through π-extension by annulation of a benzene or tropone moiety to the thiophene, oxidation, change of the heteroatom or by attachment of a donor substituent to the thiophene core. The resulting compounds display intense colors covering the entire visible spectrum. We identified structure-property relationships and their impact on the HOMO and LUMO levels. Additionally, these materials change color upon reduction and according to inâ
situ ultraviolet-visible-near infrared (UV-vis-NIR) and electron paramagnetic resonance (EPR) spectro-electrochemistry, they are promising electrochromes with cathodic color changes. Seven different electrochromic devices were constructed which all displayed a change in color upon reduction, demonstrating the potential of these new dyes in for example tintable glass.
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MEDLINE
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En
Ano de publicação:
2023
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Article