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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/19/6855 |
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| author | Cassandra J. Hager Colin D. McMillen Rakesh Sachdeva Arthur W. Martin Joseph S. Thrasher |
| author_facet | Cassandra J. Hager Colin D. McMillen Rakesh Sachdeva Arthur W. Martin Joseph S. Thrasher |
| author_sort | Cassandra J. Hager |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-10T21:40:11Z |
| format | Article |
| id | doaj.art-d04597db92d74c84b80402a2a0a88a35 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:40:11Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d04597db92d74c84b80402a2a0a88a352023-11-19T14:46:30ZengMDPI AGMolecules1420-30492023-09-012819685510.3390/molecules28196855New Fluorine-Containing Diamine Monomers for Potentially Improved PolyimidesCassandra J. Hager0Colin D. McMillen1Rakesh Sachdeva2Arthur W. Martin3Joseph S. Thrasher4Advanced Materials Research Laboratory, Department of Chemistry, Clemson University, 91 Technology Drive, Anderson, SC 29625, USAHunter Laboratory, Department of Chemistry, Clemson University, 211 S. Palmetto Blvd., Clemson, SC 29634, USAHunter Laboratory, Department of Chemistry, Clemson University, 211 S. Palmetto Blvd., Clemson, SC 29634, USAR & D Technical Center, Daikin America, Inc., 2749 Hwy 20 West, Suite A, Decatur, AL 35601, USAAdvanced Materials Research Laboratory, Department of Chemistry, Clemson University, 91 Technology Drive, Anderson, SC 29625, USATwo 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.https://www.mdpi.com/1420-3049/28/19/6855diaminesfluorine-containing monomerspolyimidessynthesis and characterizationcrystallographyhydrogen bonding |
| spellingShingle | Cassandra J. Hager Colin D. McMillen Rakesh Sachdeva Arthur W. Martin Joseph S. Thrasher New Fluorine-Containing Diamine Monomers for Potentially Improved Polyimides Molecules diamines fluorine-containing monomers polyimides synthesis and characterization crystallography hydrogen bonding |
| 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 | diamines fluorine-containing monomers polyimides synthesis and characterization crystallography hydrogen bonding |
| url | https://www.mdpi.com/1420-3049/28/19/6855 |
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