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Oxygen-Doped PAH Electrochromes: Difurano, Dipyrano, and Furano-Pyrano Containing Naphthalene-Cored Molecules

Fletcher-Charles, Jack, Ferreira, Rúben R., Abraham, Michael, Romito, Deborah, Oppel, Markus, González, Leticia and Bonifazi, Davide ORCID: 2022. Oxygen-Doped PAH Electrochromes: Difurano, Dipyrano, and Furano-Pyrano Containing Naphthalene-Cored Molecules. European Journal of Organic Chemistry 2 , e202101166. 10.1002/ejoc.202101166

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In this work, we report the synthesis of O-doped naphthalene-based electrochromes. Exploiting the CuO-mediated Pummerer oxidative cycloetherification reaction, a series of 1,4- and 1,5-disubstituted naphthalene-cored dipyrano, difurano, and furano-pyrano polycyclic aromatic hydrocarbons (PAHs) have been prepared. Steady-state UV-Vis absorption and emission investigations showed that the spectroscopic profile strongly depends on the O-doping topology, with the dipyrano and the difurano derivatives demonstrating the most red-shifted and blue-shifted electronic transition, respectively. Computational investigations revealed that the cycloetherification reaction raises the HOMO energy level (while the LUMO remains largely unaffected), with the dipyrano derivatives displaying the highest values. Spectroelectrochemical measurements showed that, depending on the O-topology and the type of O-ring, different electrochromic responses could be obtained with colour transitions featuring high contrasts involving yellow, pink, orange or blue colours.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License
Publisher: Wiley
ISSN: 1434-193X
Funders: EPSRC (PhD Studentship), EU MC-RISE “INFUSION” project (Project ID: 734834), H2020-RIA Decochrom project (Project ID: 760973)
Date of First Compliant Deposit: 29 November 2021
Date of Acceptance: 3 November 2021
Last Modified: 11 May 2023 11:34

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