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Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether
Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater t...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981047/ https://www.ncbi.nlm.nih.gov/pubmed/27547636 http://dx.doi.org/10.1002/open.201600013 |
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author | Stenger‐Smith, John D. Baldwin, Lawrence Chafin, Andrew Goodman, Paul A. |
author_facet | Stenger‐Smith, John D. Baldwin, Lawrence Chafin, Andrew Goodman, Paul A. |
author_sort | Stenger‐Smith, John D. |
collection | PubMed |
description | Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater than 99 % purity from tetrahydrofurfuryl alcohol, using (tetrahydrofuran‐2‐yl)methyl methanesulfonate as an intermediate. Additionally, we demonstrate that BTHFE can be used as a non‐volatile solvent in poly(3,4‐propylenedioxythiophene)‐based supercapacitors. Supercapacitor devices employing solutions of the ionic liquid 1‐ethyl‐3‐methyl‐imidizolium bis(trifluoromethylsulfonyl)imide in BTHFE display similar performances to those prepared by using the neat ionic liquid as an electrolyte, although solution‐based devices exhibit a somewhat higher resistance. |
format | Online Article Text |
id | pubmed-4981047 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-49810472016-08-19 Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether Stenger‐Smith, John D. Baldwin, Lawrence Chafin, Andrew Goodman, Paul A. ChemistryOpen Communications Despite the availability of a large number of alkyl tetrahydrofurfuryl ethers that have a wide range of applications, pure bis(tetrahydrofurfuryl) ether (BTHFE) has not been previously synthesized. Here, we report the synthesis of BTHFE (consisting of the RR, SS, and meso stereoisomers) at greater than 99 % purity from tetrahydrofurfuryl alcohol, using (tetrahydrofuran‐2‐yl)methyl methanesulfonate as an intermediate. Additionally, we demonstrate that BTHFE can be used as a non‐volatile solvent in poly(3,4‐propylenedioxythiophene)‐based supercapacitors. Supercapacitor devices employing solutions of the ionic liquid 1‐ethyl‐3‐methyl‐imidizolium bis(trifluoromethylsulfonyl)imide in BTHFE display similar performances to those prepared by using the neat ionic liquid as an electrolyte, although solution‐based devices exhibit a somewhat higher resistance. John Wiley and Sons Inc. 2016-05-03 /pmc/articles/PMC4981047/ /pubmed/27547636 http://dx.doi.org/10.1002/open.201600013 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (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 Stenger‐Smith, John D. Baldwin, Lawrence Chafin, Andrew Goodman, Paul A. Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title | Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title_full | Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title_fullStr | Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title_full_unstemmed | Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title_short | Synthesis and Characterization of bis(Tetrahydrofurfuryl) Ether |
title_sort | synthesis and characterization of bis(tetrahydrofurfuryl) ether |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981047/ https://www.ncbi.nlm.nih.gov/pubmed/27547636 http://dx.doi.org/10.1002/open.201600013 |
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