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HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids

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A series of novel O-doped polycyclic aromatic hydrocarbons (PAHs), 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 (PXX) 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.

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Funding Information D.B. gratefully acknowledges the EU through the MSCA-RISE (project: INFUSION, No. 734834) and MSCA-IF “ENTERPRISE” (project number: 897396) and the University of Vienna for generous financial support. B.B.B. thanks the MSCA-IF “ENTERPRISE” project for her post-doctoral fellowship. A.R. thanks the FNRS for his doctoral fellowship. The collaboration between D.B., J.P. and C.L. is supported by the MSCA-RISE INFUSION project.

Palavras-chave

Polycyclic aromatic hydrocarbons PXX Electrochromism Oxygen heterocycles Electrochromic devices

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