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

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
,
c   Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria
,
d   LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
,
d   LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal
,
c   Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria
› Author Affiliations


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.



Publication History

Received: 20 September 2022

Accepted after revision: 09 November 2022

Accepted Manuscript online:
09 November 2022

Article published online:
13 December 2022

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