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12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon

Herein we devise and execute a new synthesis of a pristine boron‐doped nanographene. Our target boron‐doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B‐doping arrangement. Our synthesis of this t...

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Autores principales: Mützel, Carina, Farrell, Jeffrey M., Shoyama, Kazutaka, Würthner, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9305547/
https://www.ncbi.nlm.nih.gov/pubmed/34914168
http://dx.doi.org/10.1002/anie.202115746
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author Mützel, Carina
Farrell, Jeffrey M.
Shoyama, Kazutaka
Würthner, Frank
author_facet Mützel, Carina
Farrell, Jeffrey M.
Shoyama, Kazutaka
Würthner, Frank
author_sort Mützel, Carina
collection PubMed
description Herein we devise and execute a new synthesis of a pristine boron‐doped nanographene. Our target boron‐doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B‐doping arrangement. Our synthesis of this target, a doubly B‐doped hexabenzopentacene (B ( 2 ) ‐HBP), employs six net C−H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr(3)/AlCl(3)/2,6‐dichloropyridine‐mediated C−H borylation steps. As predicted by our calculations, B ( 2 ) ‐HBP absorbs strongly in the visible region and emits in the NIR up to 1150  nm in o‐dichlorobenzene solutions. Furthermore, B ( 2 ) ‐HBP possesses a very low LUMO level, showing two reversible reductions at −1.00  V and −1.17  V vs. Fc(+)/Fc. Our methodology is surprisingly selective despite its implementation of unfunctionalized precursors and offers a new approach to the synthesis of pristine B‐doped polycyclic aromatic hydrocarbons.
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spelling pubmed-93055472022-07-28 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon Mützel, Carina Farrell, Jeffrey M. Shoyama, Kazutaka Würthner, Frank Angew Chem Int Ed Engl Communications Herein we devise and execute a new synthesis of a pristine boron‐doped nanographene. Our target boron‐doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B‐doping arrangement. Our synthesis of this target, a doubly B‐doped hexabenzopentacene (B ( 2 ) ‐HBP), employs six net C−H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr(3)/AlCl(3)/2,6‐dichloropyridine‐mediated C−H borylation steps. As predicted by our calculations, B ( 2 ) ‐HBP absorbs strongly in the visible region and emits in the NIR up to 1150  nm in o‐dichlorobenzene solutions. Furthermore, B ( 2 ) ‐HBP possesses a very low LUMO level, showing two reversible reductions at −1.00  V and −1.17  V vs. Fc(+)/Fc. Our methodology is surprisingly selective despite its implementation of unfunctionalized precursors and offers a new approach to the synthesis of pristine B‐doped polycyclic aromatic hydrocarbons. John Wiley and Sons Inc. 2022-01-03 2022-02-14 /pmc/articles/PMC9305547/ /pubmed/34914168 http://dx.doi.org/10.1002/anie.202115746 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Mützel, Carina
Farrell, Jeffrey M.
Shoyama, Kazutaka
Würthner, Frank
12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title_full 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title_fullStr 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title_full_unstemmed 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title_short 12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon
title_sort 12b,24b‐diborahexabenzo[a,c,fg,l,n,qr]pentacene: a low‐lumo boron‐doped polycyclic aromatic hydrocarbon
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9305547/
https://www.ncbi.nlm.nih.gov/pubmed/34914168
http://dx.doi.org/10.1002/anie.202115746
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