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A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene

A representative, low‐temperature gas‐phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C(22)H(14)) along with its benzo[a]tetracene isomer (C(22)H(14)) is unraveled by probing the elementary reaction of the 2‐tetracenyl radical (C(18)H(1...

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Autores principales: Zhao, Long, Kaiser, Ralf I., Lu, Wenchao, Ahmed, Musahid, Evseev, Mikhail M., Bashkirov, Eugene K., Azyazov, Valeriy N., Tönshoff, Christina, Reicherter, Florian, Bettinger, Holger F., Mebel, Alexander M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7383502/
https://www.ncbi.nlm.nih.gov/pubmed/32266773
http://dx.doi.org/10.1002/anie.202003402
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author Zhao, Long
Kaiser, Ralf I.
Lu, Wenchao
Ahmed, Musahid
Evseev, Mikhail M.
Bashkirov, Eugene K.
Azyazov, Valeriy N.
Tönshoff, Christina
Reicherter, Florian
Bettinger, Holger F.
Mebel, Alexander M.
author_facet Zhao, Long
Kaiser, Ralf I.
Lu, Wenchao
Ahmed, Musahid
Evseev, Mikhail M.
Bashkirov, Eugene K.
Azyazov, Valeriy N.
Tönshoff, Christina
Reicherter, Florian
Bettinger, Holger F.
Mebel, Alexander M.
author_sort Zhao, Long
collection PubMed
description A representative, low‐temperature gas‐phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C(22)H(14)) along with its benzo[a]tetracene isomer (C(22)H(14)) is unraveled by probing the elementary reaction of the 2‐tetracenyl radical (C(18)H(11) (.)) with vinylacetylene (C(4)H(4)). The pathway to pentacene—a prototype polyacene and a fundamental molecular building block in graphenes, fullerenes, and carbon nanotubes—is facilitated by a barrierless, vinylacetylene mediated gas‐phase process thus disputing conventional hypotheses that synthesis of polycyclic aromatic hydrocarbons (PAHs) solely proceeds at elevated temperatures. This low‐temperature pathway can launch isomer‐selective routes to aromatic structures through submerged reaction barriers, resonantly stabilized free‐radical intermediates, and methodical ring annulation in deep space eventually changing our perception about the chemistry of carbon in our universe.
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spelling pubmed-73835022020-07-27 A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene Zhao, Long Kaiser, Ralf I. Lu, Wenchao Ahmed, Musahid Evseev, Mikhail M. Bashkirov, Eugene K. Azyazov, Valeriy N. Tönshoff, Christina Reicherter, Florian Bettinger, Holger F. Mebel, Alexander M. Angew Chem Int Ed Engl Communications A representative, low‐temperature gas‐phase reaction mechanism synthesizing polyacenes via ring annulation exemplified by the formation of pentacene (C(22)H(14)) along with its benzo[a]tetracene isomer (C(22)H(14)) is unraveled by probing the elementary reaction of the 2‐tetracenyl radical (C(18)H(11) (.)) with vinylacetylene (C(4)H(4)). The pathway to pentacene—a prototype polyacene and a fundamental molecular building block in graphenes, fullerenes, and carbon nanotubes—is facilitated by a barrierless, vinylacetylene mediated gas‐phase process thus disputing conventional hypotheses that synthesis of polycyclic aromatic hydrocarbons (PAHs) solely proceeds at elevated temperatures. This low‐temperature pathway can launch isomer‐selective routes to aromatic structures through submerged reaction barriers, resonantly stabilized free‐radical intermediates, and methodical ring annulation in deep space eventually changing our perception about the chemistry of carbon in our universe. John Wiley and Sons Inc. 2020-05-11 2020-07-06 /pmc/articles/PMC7383502/ /pubmed/32266773 http://dx.doi.org/10.1002/anie.202003402 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Zhao, Long
Kaiser, Ralf I.
Lu, Wenchao
Ahmed, Musahid
Evseev, Mikhail M.
Bashkirov, Eugene K.
Azyazov, Valeriy N.
Tönshoff, Christina
Reicherter, Florian
Bettinger, Holger F.
Mebel, Alexander M.
A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title_full A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title_fullStr A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title_full_unstemmed A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title_short A Free‐Radical Prompted Barrierless Gas‐Phase Synthesis of Pentacene
title_sort free‐radical prompted barrierless gas‐phase synthesis of pentacene
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7383502/
https://www.ncbi.nlm.nih.gov/pubmed/32266773
http://dx.doi.org/10.1002/anie.202003402
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