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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
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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. |
format | Online Article Text |
id | pubmed-6268729 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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