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New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides
Two new fluorine-containing diamine monomers were designed with the goal of reducing charge transfer complex (CTC) interactions between neighboring chains in polyimides (i.e., high transparency/low color) while hopefully maintaining the well-known thermal stability and flexibility generally associat...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574420/ https://www.ncbi.nlm.nih.gov/pubmed/37836698 http://dx.doi.org/10.3390/molecules28196855 |
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author | Hager, Cassandra J. McMillen, Colin D. Sachdeva, Rakesh Martin, Arthur W. Thrasher, Joseph S. |
author_facet | Hager, Cassandra J. McMillen, Colin D. Sachdeva, Rakesh Martin, Arthur W. Thrasher, Joseph S. |
author_sort | Hager, Cassandra J. |
collection | PubMed |
description | Two new fluorine-containing diamine monomers were designed with the goal of reducing charge transfer complex (CTC) interactions between neighboring chains in polyimides (i.e., high transparency/low color) while hopefully maintaining the well-known thermal stability and flexibility generally associated with polyimides. The proposed diamines have been prepared through (1) the functionalization of 1,3-bis[(pentafluorobenzyl)oxy]benzene with 4-aminophenol and (2) the addition of 2-chloro-5-nitrobenzotrifluoride to 4,4′-bicyclohexanol followed by reduction of the resulting dinitro compound. The new compounds have been characterized by multinuclear NMR and IR spectroscopy and high-resolution liquid chromatography-mass spectrometry as well as single-crystal X-ray diffraction on the new diamine prepared from 4,4′-bicyclohexanol. Not only was the structure of the proposed new diamine confirmed, but another interesting example of hydrogen bonding between an N-H proton and the π-system of an aromatic ring was observed and documented. Initial polymerizations have been carried out via the two-step imidization process. |
format | Online Article Text |
id | pubmed-10574420 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-105744202023-10-14 New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides Hager, Cassandra J. McMillen, Colin D. Sachdeva, Rakesh Martin, Arthur W. Thrasher, Joseph S. Molecules Article Two new fluorine-containing diamine monomers were designed with the goal of reducing charge transfer complex (CTC) interactions between neighboring chains in polyimides (i.e., high transparency/low color) while hopefully maintaining the well-known thermal stability and flexibility generally associated with polyimides. The proposed diamines have been prepared through (1) the functionalization of 1,3-bis[(pentafluorobenzyl)oxy]benzene with 4-aminophenol and (2) the addition of 2-chloro-5-nitrobenzotrifluoride to 4,4′-bicyclohexanol followed by reduction of the resulting dinitro compound. The new compounds have been characterized by multinuclear NMR and IR spectroscopy and high-resolution liquid chromatography-mass spectrometry as well as single-crystal X-ray diffraction on the new diamine prepared from 4,4′-bicyclohexanol. Not only was the structure of the proposed new diamine confirmed, but another interesting example of hydrogen bonding between an N-H proton and the π-system of an aromatic ring was observed and documented. Initial polymerizations have been carried out via the two-step imidization process. MDPI 2023-09-28 /pmc/articles/PMC10574420/ /pubmed/37836698 http://dx.doi.org/10.3390/molecules28196855 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Hager, Cassandra J. McMillen, Colin D. Sachdeva, Rakesh Martin, Arthur W. Thrasher, Joseph S. New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title | New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title_full | New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title_fullStr | New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title_full_unstemmed | New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title_short | New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides |
title_sort | new fluorine-containing diamine monomers for potentially improved polyimides |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574420/ https://www.ncbi.nlm.nih.gov/pubmed/37836698 http://dx.doi.org/10.3390/molecules28196855 |
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