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An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor

Pentacene is an organic semiconductor used in a variety of thin-film organic electronic devices. Although at least six separate syntheses of pentacene are known (two from dihydropentacenes, two from 6,13-pentacenedione and two from 6,13-dihydro-6,13-dihydroxypentacene), none is ideal and several uti...

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Detalles Bibliográficos
Autores principales: Pramanik, Chandrani, Miller, Glen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268729/
https://www.ncbi.nlm.nih.gov/pubmed/22522393
http://dx.doi.org/10.3390/molecules17044625
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author Pramanik, Chandrani
Miller, Glen P.
author_facet Pramanik, Chandrani
Miller, Glen P.
author_sort Pramanik, Chandrani
collection PubMed
description Pentacene is an organic semiconductor used in a variety of thin-film organic electronic devices. Although at least six separate syntheses of pentacene are known (two from dihydropentacenes, two from 6,13-pentacenedione and two from 6,13-dihydro-6,13-dihydroxypentacene), none is ideal and several utilize elevated temperatures that may facilitate the oxidation of pentacene as it is produced. Here, we present a fast (~2 min of reaction time), simple, high-yielding (≥90%), low temperature synthesis of pentacene from readily available 6,13-dihydro-6,13-dihydroxypentacene. Further, we discuss the mechanism of this highly efficient reaction. With this improved synthesis, researchers gain rapid, affordable access to high purity pentacene in excellent yield and without the need for a time consuming sublimation.
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spelling pubmed-62687292018-12-11 An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor Pramanik, Chandrani Miller, Glen P. Molecules Article Pentacene is an organic semiconductor used in a variety of thin-film organic electronic devices. Although at least six separate syntheses of pentacene are known (two from dihydropentacenes, two from 6,13-pentacenedione and two from 6,13-dihydro-6,13-dihydroxypentacene), none is ideal and several utilize elevated temperatures that may facilitate the oxidation of pentacene as it is produced. Here, we present a fast (~2 min of reaction time), simple, high-yielding (≥90%), low temperature synthesis of pentacene from readily available 6,13-dihydro-6,13-dihydroxypentacene. Further, we discuss the mechanism of this highly efficient reaction. With this improved synthesis, researchers gain rapid, affordable access to high purity pentacene in excellent yield and without the need for a time consuming sublimation. MDPI 2012-04-20 /pmc/articles/PMC6268729/ /pubmed/22522393 http://dx.doi.org/10.3390/molecules17044625 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Pramanik, Chandrani
Miller, Glen P.
An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title_full An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title_fullStr An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title_full_unstemmed An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title_short An Improved Synthesis of Pentacene: Rapid Access to a Benchmark Organic Semiconductor
title_sort improved synthesis of pentacene: rapid access to a benchmark organic semiconductor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268729/
https://www.ncbi.nlm.nih.gov/pubmed/22522393
http://dx.doi.org/10.3390/molecules17044625
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