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

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

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Abstract

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.

Original language	English
Pages (from-to)	241-254
Number of pages	14
Journal	Organic Materials
Volume	4
DOIs	https://doi.org/10.1055/a-1976-0291
Publication status	Published - Dec 2022

Keywords

Polycyclic aromatic hydrocarbons
PXX
Electrochromism
Oxygen heterocycles
Electrochromic devices

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10.1055/a-1976-0291Licence: CC BY-NC-ND

HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids Synthesis of Electrochromic Alkoxy-Decorated XanthenoxanthenesFinal published version, 10.2 MBLicence: CC BY-NC-ND

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@article{b140c5fb2d1943108f45ab12dd46988c,

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

abstract = "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.",

keywords = "Polycyclic aromatic hydrocarbons, PXX, Electrochromism, Oxygen heterocycles, Electrochromic devices",

author = "Alexandre Rossignon and Berna, {Beatrice Berionni} and Parola, {A. Jorge} and Laia, {C{\'e}sar A. T.} and Davide Bonifazi",

note = "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.",

year = "2022",

month = dec,

doi = "10.1055/a-1976-0291",

language = "English",

volume = "4",

pages = "241--254",

journal = "Organic Materials",

}

TY - JOUR

T1 - HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids

T2 - Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

AU - Rossignon, Alexandre

AU - Berna, Beatrice Berionni

AU - Parola, A. Jorge

AU - Laia, César A. T.

AU - Bonifazi, Davide

N1 - 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.

PY - 2022/12

Y1 - 2022/12

N2 - 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.

AB - 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.

KW - Polycyclic aromatic hydrocarbons

KW - PXX

KW - Electrochromism

KW - Oxygen heterocycles

KW - Electrochromic devices

UR - https://doi.org/10.1055/a-1976-0291

U2 - 10.1055/a-1976-0291

DO - 10.1055/a-1976-0291

M3 - Article

VL - 4

SP - 241

EP - 254

JO - Organic Materials

JF - Organic Materials

ER -

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

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Keywords

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