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Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation
A catalyst-free Schiff base reaction was applied to synthesize two imine-linked covalent organic frameworks (COFs). The condensation reaction of 1,3,5-tris-(4-aminophenyl)triazine (TAPT) with 4,4′-biphenyldicarboxaldehyde led to the structure of HHU-COF-1 (HHU = Heinrich-Heine University). The fluor...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9031922/ https://www.ncbi.nlm.nih.gov/pubmed/35454500 http://dx.doi.org/10.3390/ma15082807 |
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author | Bügel, Stefanie Hähnel, Malte Kunde, Tom de Sousa Amadeu, Nader Sun, Yangyang Spieß, Alex Beglau, Thi Hai Yen Schmidt, Bernd M. Janiak, Christoph |
author_facet | Bügel, Stefanie Hähnel, Malte Kunde, Tom de Sousa Amadeu, Nader Sun, Yangyang Spieß, Alex Beglau, Thi Hai Yen Schmidt, Bernd M. Janiak, Christoph |
author_sort | Bügel, Stefanie |
collection | PubMed |
description | A catalyst-free Schiff base reaction was applied to synthesize two imine-linked covalent organic frameworks (COFs). The condensation reaction of 1,3,5-tris-(4-aminophenyl)triazine (TAPT) with 4,4′-biphenyldicarboxaldehyde led to the structure of HHU-COF-1 (HHU = Heinrich-Heine University). The fluorinated analog HHU-COF-2 was obtained with 2,2′,3,3′,5,5′,6,6′-octafluoro-4,4′-biphenyldicarboxaldehyde. Solid-state NMR, infrared spectroscopy, X-ray photoelectron spectroscopy, and elemental analysis confirmed the successful formation of the two network structures. The crystalline materials are characterized by high Brunauer–Emmett–Teller surface areas of 2352 m(2)/g for HHU-COF-1 and 1356 m(2)/g for HHU-COF-2. The products of a larger-scale synthesis were applied to prepare mixed-matrix membranes (MMMs) with the polymer Matrimid. CO(2)/CH(4) permeation tests revealed a moderate increase in CO(2) permeability at constant selectivity for HHU-COF-1 as a dispersed phase, whereas application of the fluorinated COF led to a CO(2)/CH(4) selectivity increase from 42 for the pure Matrimid membrane to 51 for 8 wt% of HHU-COF-2 and a permeability increase from 6.8 to 13.0 Barrer for the 24 wt% MMM. |
format | Online Article Text |
id | pubmed-9031922 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-90319222022-04-23 Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation Bügel, Stefanie Hähnel, Malte Kunde, Tom de Sousa Amadeu, Nader Sun, Yangyang Spieß, Alex Beglau, Thi Hai Yen Schmidt, Bernd M. Janiak, Christoph Materials (Basel) Article A catalyst-free Schiff base reaction was applied to synthesize two imine-linked covalent organic frameworks (COFs). The condensation reaction of 1,3,5-tris-(4-aminophenyl)triazine (TAPT) with 4,4′-biphenyldicarboxaldehyde led to the structure of HHU-COF-1 (HHU = Heinrich-Heine University). The fluorinated analog HHU-COF-2 was obtained with 2,2′,3,3′,5,5′,6,6′-octafluoro-4,4′-biphenyldicarboxaldehyde. Solid-state NMR, infrared spectroscopy, X-ray photoelectron spectroscopy, and elemental analysis confirmed the successful formation of the two network structures. The crystalline materials are characterized by high Brunauer–Emmett–Teller surface areas of 2352 m(2)/g for HHU-COF-1 and 1356 m(2)/g for HHU-COF-2. The products of a larger-scale synthesis were applied to prepare mixed-matrix membranes (MMMs) with the polymer Matrimid. CO(2)/CH(4) permeation tests revealed a moderate increase in CO(2) permeability at constant selectivity for HHU-COF-1 as a dispersed phase, whereas application of the fluorinated COF led to a CO(2)/CH(4) selectivity increase from 42 for the pure Matrimid membrane to 51 for 8 wt% of HHU-COF-2 and a permeability increase from 6.8 to 13.0 Barrer for the 24 wt% MMM. MDPI 2022-04-11 /pmc/articles/PMC9031922/ /pubmed/35454500 http://dx.doi.org/10.3390/ma15082807 Text en © 2022 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 Bügel, Stefanie Hähnel, Malte Kunde, Tom de Sousa Amadeu, Nader Sun, Yangyang Spieß, Alex Beglau, Thi Hai Yen Schmidt, Bernd M. Janiak, Christoph Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title | Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title_full | Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title_fullStr | Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title_full_unstemmed | Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title_short | Synthesis and Characterization of a Crystalline Imine-Based Covalent Organic Framework with Triazine Node and Biphenyl Linker and Its Fluorinated Derivate for CO(2)/CH(4) Separation |
title_sort | synthesis and characterization of a crystalline imine-based covalent organic framework with triazine node and biphenyl linker and its fluorinated derivate for co(2)/ch(4) separation |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9031922/ https://www.ncbi.nlm.nih.gov/pubmed/35454500 http://dx.doi.org/10.3390/ma15082807 |
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