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CC BY-NC-ND 4.0 · Organic Materials 2022; 4(04): 240-254
DOI: 10.1055/a-1976-0291
Original Article

HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

Alexandre Rossignon 
a   Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium
b   School of Chemistry of Cardiff University, Cardiff University, CF10 3 AT Cardiff, United Kingdom
,
Beatrice Berionni Berna 
c   Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria
,
A. Jorge Parola 
d   LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
,
César A. T. Laia 
d   LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
,
Davide Bonifazi 
c   Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria
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Abstract

A series of novel O-doped polycyclic aromatic hydrocarbons, bearing a different number of electron-donating alkoxy substituents, has been prepared using a novel copper-promoted anaerobic protocol for the cyclisation of highly electron rich peri-xanthenoxanthene molecular modules. The effect of the number and position of the alkoxy substituents on the optoelectronic properties has thus been investigated, unveiling p-type semiconducting properties. All molecules displayed a significant colour change upon oxidation, suggesting that these compounds can be used to devise chromogenic materials to engineer electrochromic devices.

Key words

polycyclic aromatic hydrocarbons - PXX - electrochromism - oxygen heterocycles - electrochromic devices

Supporting Information



Publication History

Received: 20 September 2022

Accepted after revision: 09 November 2022

Accepted Manuscript online:
09 November 2022

Article published online:
13 December 2022

© 2022. The authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
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