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Dibenzannulated peri-acenoacenes from anthanthrene derivatives
A series of dibenzannulated phenyl-annulated [4,2]peri-acenoacenes have been synthesized in three straightforward steps from 4,10-dibromoanthanthrone (vat orange 3). The phenyl bisannulation of [4,2]peri-acenoacene provides extra stability by increasing the overall aromatic character of the molecule...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10530754/ https://www.ncbi.nlm.nih.gov/pubmed/37772122 http://dx.doi.org/10.1039/d3sc02898d |
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author | Lirette, Frédéric Darvish, Ali Zhou, Zheng Wei, Zheng Renn, Lukas Petrukhina, Marina A. Weitz, R. Thomas Morin, Jean-François |
author_facet | Lirette, Frédéric Darvish, Ali Zhou, Zheng Wei, Zheng Renn, Lukas Petrukhina, Marina A. Weitz, R. Thomas Morin, Jean-François |
author_sort | Lirette, Frédéric |
collection | PubMed |
description | A series of dibenzannulated phenyl-annulated [4,2]peri-acenoacenes have been synthesized in three straightforward steps from 4,10-dibromoanthanthrone (vat orange 3). The phenyl bisannulation of [4,2]peri-acenoacene provides extra stability by increasing the overall aromatic character of the molecules, and allows for a 45–80% increase of the molar extinction coefficient (ε) compared to their [5,2]peri-acenoacene isomers. Depending on the substituents attached to the π-conjugated core, some derivatives exhibit strong aggregation in the solid state with association constant (K(a)) up to 255 M(−1), resulting in a significant broadening of the absorption spectrum and a substantial decrease of the bandgap value (more than 0.3 V) from solution to the solid state. One [4,2]peri-acenoacene derivative was doubly reduced using cesium and the crystal structure of the resulting salt has been obtained. Field-effect transistors showing a temperature-dependent hole mobility have been tested. |
format | Online Article Text |
id | pubmed-10530754 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-105307542023-09-28 Dibenzannulated peri-acenoacenes from anthanthrene derivatives Lirette, Frédéric Darvish, Ali Zhou, Zheng Wei, Zheng Renn, Lukas Petrukhina, Marina A. Weitz, R. Thomas Morin, Jean-François Chem Sci Chemistry A series of dibenzannulated phenyl-annulated [4,2]peri-acenoacenes have been synthesized in three straightforward steps from 4,10-dibromoanthanthrone (vat orange 3). The phenyl bisannulation of [4,2]peri-acenoacene provides extra stability by increasing the overall aromatic character of the molecules, and allows for a 45–80% increase of the molar extinction coefficient (ε) compared to their [5,2]peri-acenoacene isomers. Depending on the substituents attached to the π-conjugated core, some derivatives exhibit strong aggregation in the solid state with association constant (K(a)) up to 255 M(−1), resulting in a significant broadening of the absorption spectrum and a substantial decrease of the bandgap value (more than 0.3 V) from solution to the solid state. One [4,2]peri-acenoacene derivative was doubly reduced using cesium and the crystal structure of the resulting salt has been obtained. Field-effect transistors showing a temperature-dependent hole mobility have been tested. The Royal Society of Chemistry 2023-08-30 /pmc/articles/PMC10530754/ /pubmed/37772122 http://dx.doi.org/10.1039/d3sc02898d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Lirette, Frédéric Darvish, Ali Zhou, Zheng Wei, Zheng Renn, Lukas Petrukhina, Marina A. Weitz, R. Thomas Morin, Jean-François Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title | Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title_full | Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title_fullStr | Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title_full_unstemmed | Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title_short | Dibenzannulated peri-acenoacenes from anthanthrene derivatives |
title_sort | dibenzannulated peri-acenoacenes from anthanthrene derivatives |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10530754/ https://www.ncbi.nlm.nih.gov/pubmed/37772122 http://dx.doi.org/10.1039/d3sc02898d |
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