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

Alexandre Rossignon; Beatrice Berionni Berna; A. Jorge Parola; César A. T. Laia; Davide Bonifazi

doi:10.1055/a-1976-0291

Organic Materials, Inhaltsverzeichnis

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

^aDepartment of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, 5000 Namur, Belgium

^bSchool of Chemistry of Cardiff University, Cardiff University, CF10 3 AT Cardiff, United Kingdom

,

Beatrice Berionni Berna

^cInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria

,

A. Jorge Parola

^dLAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal

,

César A. T. Laia

^dLAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, FCT NOVA, NOVA University of Lisbon, 2829-516 Caparica, Portugal

,

Davide Bonifazi

^cInstitute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria

› Institutsangaben

Abstract

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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

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Referenzen

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Zusatzmaterial

Supporting Information for this article is available online.