Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines
Heteroaromatic polyimides (PIs) containing benzimidazole have attracted tremendous attention due to their positive impact on the properties of PIs. Some research on PIs containing 4,4′-[5,5′-bi-1<i>H</i>-benzimidazole]-2,2′-diylbis-benzenamine (<b>4-AB</b>) has been reported....
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MDPI AG
2023-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/4889 |
| _version_ | 1797591231834882048 |
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| author | Meng Lian Feng Zheng Lingbin Meng Fei Zhao Jun Liu Jimei Song Qinghua Lu |
| author_facet | Meng Lian Feng Zheng Lingbin Meng Fei Zhao Jun Liu Jimei Song Qinghua Lu |
| author_sort | Meng Lian |
| collection | DOAJ |
| description | Heteroaromatic polyimides (PIs) containing benzimidazole have attracted tremendous attention due to their positive impact on the properties of PIs. Some research on PIs containing 4,4′-[5,5′-bi-1<i>H</i>-benzimidazole]-2,2′-diylbis-benzenamine (<b>4-AB</b>) has been reported. However, reports are lacking on homo-polyimides (homo-PIs) containing 3,3′-[5,5′-bi-1<i>H</i>-benzimidazole]-2,2′-diylbis-benzenamine (<b>3-AB</b>), which is one of the isomers of <b>4-AB</b>. In this paper, the influence of amino groups’ positions on the performance of homo-PIs was investigated. It was found that the net charge of the amine N group in <b>4-AB</b> was lower than that of <b>3-AB</b>, resulting in higher reactivity of <b>4-AB</b>. Consequently, PIs containing <b>4-AB</b> displayed better mechanical performance. Molecular simulation confirmed that <b>3-AB</b> and its corresponding PI chain exhibited distorted conformation, leading to the PI films containing <b>3-AB</b> having a lighter color. In addition, the <b>3-AB</b> structure was calculated to have higher rotational energy compared to <b>4-AB</b>, resulting in a higher glass transition temperature (<i>T</i><sub>g</sub>) in PIs prepared from <b>3-AB</b>. On the other hand, PIs containing <b>4-AB</b> exhibited a higher level of molecular linearity, leading to a lower coefficient of thermal expansion (CTE) compared to PIs prepared from <b>3-AB</b>. Furthermore, all PIs showed higher thermal stability with a 5% weight loss temperature above 530 °C and <i>T</i><sub>g</sub> higher than 400 °C. |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:34:33Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c32708aa4e464aa58abe79d5881173922023-11-18T17:04:59ZengMDPI AGMolecules1420-30492023-06-012813488910.3390/molecules28134889Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole DiaminesMeng Lian0Feng Zheng1Lingbin Meng2Fei Zhao3Jun Liu4Jimei Song5Qinghua Lu6Shandong Engineering Laboratory for Clean Utilization of Chemical Resources, Weifang University of Science and Technology, Weifang 262700, ChinaSchool of Chemical Science and Engineering, Tongji University, Siping Road 1239, Shanghai 200092, ChinaShandong Engineering Laboratory for Clean Utilization of Chemical Resources, Weifang University of Science and Technology, Weifang 262700, ChinaShandong Engineering Laboratory for Clean Utilization of Chemical Resources, Weifang University of Science and Technology, Weifang 262700, ChinaShandong Engineering Laboratory for Clean Utilization of Chemical Resources, Weifang University of Science and Technology, Weifang 262700, ChinaShandong Engineering Laboratory for Clean Utilization of Chemical Resources, Weifang University of Science and Technology, Weifang 262700, ChinaShanghai Key Laboratory of Electrical Insulation and Thermal Aging, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, ChinaHeteroaromatic polyimides (PIs) containing benzimidazole have attracted tremendous attention due to their positive impact on the properties of PIs. Some research on PIs containing 4,4′-[5,5′-bi-1<i>H</i>-benzimidazole]-2,2′-diylbis-benzenamine (<b>4-AB</b>) has been reported. However, reports are lacking on homo-polyimides (homo-PIs) containing 3,3′-[5,5′-bi-1<i>H</i>-benzimidazole]-2,2′-diylbis-benzenamine (<b>3-AB</b>), which is one of the isomers of <b>4-AB</b>. In this paper, the influence of amino groups’ positions on the performance of homo-PIs was investigated. It was found that the net charge of the amine N group in <b>4-AB</b> was lower than that of <b>3-AB</b>, resulting in higher reactivity of <b>4-AB</b>. Consequently, PIs containing <b>4-AB</b> displayed better mechanical performance. Molecular simulation confirmed that <b>3-AB</b> and its corresponding PI chain exhibited distorted conformation, leading to the PI films containing <b>3-AB</b> having a lighter color. In addition, the <b>3-AB</b> structure was calculated to have higher rotational energy compared to <b>4-AB</b>, resulting in a higher glass transition temperature (<i>T</i><sub>g</sub>) in PIs prepared from <b>3-AB</b>. On the other hand, PIs containing <b>4-AB</b> exhibited a higher level of molecular linearity, leading to a lower coefficient of thermal expansion (CTE) compared to PIs prepared from <b>3-AB</b>. Furthermore, all PIs showed higher thermal stability with a 5% weight loss temperature above 530 °C and <i>T</i><sub>g</sub> higher than 400 °C.https://www.mdpi.com/1420-3049/28/13/4889heteroaromatic polyimidesisomeric diaminebis-benzimidazole |
| spellingShingle | Meng Lian Feng Zheng Lingbin Meng Fei Zhao Jun Liu Jimei Song Qinghua Lu Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines Molecules heteroaromatic polyimides isomeric diamine bis-benzimidazole |
| title | Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines |
| title_full | Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines |
| title_fullStr | Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines |
| title_full_unstemmed | Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines |
| title_short | Comparison of Homo-Polyimide Films Derived from Two Isomeric Bis-Benzimidazole Diamines |
| title_sort | comparison of homo polyimide films derived from two isomeric bis benzimidazole diamines |
| topic | heteroaromatic polyimides isomeric diamine bis-benzimidazole |
| url | https://www.mdpi.com/1420-3049/28/13/4889 |
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