Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution
This study reports on the synthesis and characterization of novel perfluorinated organic polymers with azo- and azomethine-based linkers using nucleophilic aromatic substitution. The polymers were synthesized via the incorporation of decafluorobiphenyl and hexafluorobenzene linkers with diphenols in...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-10-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/15/20/4191 |
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| author | Suha S. Altarawneh Hani M. El-Kaderi Alexander J. Richard Osama M. Alakayleh Ibtesam Y. Aljaafreh Mansour H. Almatarneh Taher S. Ababneh Lo’ay A. Al-Momani Rawan H. Aldalabeeh |
| author_facet | Suha S. Altarawneh Hani M. El-Kaderi Alexander J. Richard Osama M. Alakayleh Ibtesam Y. Aljaafreh Mansour H. Almatarneh Taher S. Ababneh Lo’ay A. Al-Momani Rawan H. Aldalabeeh |
| author_sort | Suha S. Altarawneh |
| collection | DOAJ |
| description | This study reports on the synthesis and characterization of novel perfluorinated organic polymers with azo- and azomethine-based linkers using nucleophilic aromatic substitution. The polymers were synthesized via the incorporation of decafluorobiphenyl and hexafluorobenzene linkers with diphenols in the basic medium. The variation in the linkers allowed the synthesis of polymers with different fluorine and nitrogen contents. The rich fluorine polymers were slightly soluble in THF and have shown molecular weights ranging from 4886 to 11,948 g/mol. All polymers exhibit thermal stability in the range of 350–500 °C, which can be attributed to their structural geometry, elemental contents, branching, and cross-linking. For instance, the cross-linked polymers with high nitrogen content, DAB-Z-1h and DAB-Z-1O, are more stable than azomethine-based polymers. The cross-linking was characterized by porosity measurements. The azo-based polymer exhibited the highest surface area of 770 m<sup>2</sup>/g with a pore volume of 0.35 cm<sup>3</sup>/g, while the open-chain azomethine-based polymer revealed the lowest surface area of 285 m<sup>2</sup>/g with a pore volume of 0.0872 cm<sup>3</sup>/g. Porous structures with varied hydrophobicities were investigated as adsorbents for separating water-benzene and water-phenol mixtures and selectively binding methane/carbon dioxide gases from the air. The most hydrophobic polymers containing the decafluorbiphenyl linker were suitable for benzene separation, while the best methane uptake values were 6.14 and 3.46 mg/g for DAB-Z-1O and DAB-A-1O, respectively. On the other hand, DAB-Z-1h, with the highest surface area and being rich in nitrogen sites, has recorded the highest CO<sub>2</sub> uptake at 298 K (17.25 mg/g). |
| first_indexed | 2024-03-10T20:57:01Z |
| format | Article |
| id | doaj.art-d3898c5e8dd24b91b0b65312b4c80c65 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T20:57:01Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-d3898c5e8dd24b91b0b65312b4c80c652023-11-19T17:52:30ZengMDPI AGPolymers2073-43602023-10-011520419110.3390/polym15204191Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic SubstitutionSuha S. Altarawneh0Hani M. El-Kaderi1Alexander J. Richard2Osama M. Alakayleh3Ibtesam Y. Aljaafreh4Mansour H. Almatarneh5Taher S. Ababneh6Lo’ay A. Al-Momani7Rawan H. Aldalabeeh8Department of Chemistry and Chemical Technology, Tafila Technical University, Tafila 66110, JordanDepartment of Chemistry, Virginia Commonwealth University, Richmond, VA 23284, USADepartment of Chemistry, Virginia Commonwealth University, Richmond, VA 23284, USADepartment of Chemistry and Chemical Technology, Tafila Technical University, Tafila 66110, JordanDepartment of Chemistry and Chemical Technology, Tafila Technical University, Tafila 66110, JordanDepartment of Chemistry, University of Jordan, Amman 11942, JordanDepartment of Chemistry, Yarmouk University, Irbid 21163, JordanDepartment of Chemistry, Faculty of Science, The Hashemite University, Zarqa 13133, JordanDepartment of Chemistry and Chemical Technology, Tafila Technical University, Tafila 66110, JordanThis study reports on the synthesis and characterization of novel perfluorinated organic polymers with azo- and azomethine-based linkers using nucleophilic aromatic substitution. The polymers were synthesized via the incorporation of decafluorobiphenyl and hexafluorobenzene linkers with diphenols in the basic medium. The variation in the linkers allowed the synthesis of polymers with different fluorine and nitrogen contents. The rich fluorine polymers were slightly soluble in THF and have shown molecular weights ranging from 4886 to 11,948 g/mol. All polymers exhibit thermal stability in the range of 350–500 °C, which can be attributed to their structural geometry, elemental contents, branching, and cross-linking. For instance, the cross-linked polymers with high nitrogen content, DAB-Z-1h and DAB-Z-1O, are more stable than azomethine-based polymers. The cross-linking was characterized by porosity measurements. The azo-based polymer exhibited the highest surface area of 770 m<sup>2</sup>/g with a pore volume of 0.35 cm<sup>3</sup>/g, while the open-chain azomethine-based polymer revealed the lowest surface area of 285 m<sup>2</sup>/g with a pore volume of 0.0872 cm<sup>3</sup>/g. Porous structures with varied hydrophobicities were investigated as adsorbents for separating water-benzene and water-phenol mixtures and selectively binding methane/carbon dioxide gases from the air. The most hydrophobic polymers containing the decafluorbiphenyl linker were suitable for benzene separation, while the best methane uptake values were 6.14 and 3.46 mg/g for DAB-Z-1O and DAB-A-1O, respectively. On the other hand, DAB-Z-1h, with the highest surface area and being rich in nitrogen sites, has recorded the highest CO<sub>2</sub> uptake at 298 K (17.25 mg/g).https://www.mdpi.com/2073-4360/15/20/4191per-fluorinated organic polymersnucleophilic aromatic substitutionazomethine-based linkersazo-based linkersporosity measurementsenvironmental applications |
| spellingShingle | Suha S. Altarawneh Hani M. El-Kaderi Alexander J. Richard Osama M. Alakayleh Ibtesam Y. Aljaafreh Mansour H. Almatarneh Taher S. Ababneh Lo’ay A. Al-Momani Rawan H. Aldalabeeh Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution Polymers per-fluorinated organic polymers nucleophilic aromatic substitution azomethine-based linkers azo-based linkers porosity measurements environmental applications |
| title | Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution |
| title_full | Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution |
| title_fullStr | Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution |
| title_full_unstemmed | Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution |
| title_short | Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution |
| title_sort | synthesis characterization and environmental applications of novel per fluorinated organic polymers with azo and azomethine based linkers via nucleophilic aromatic substitution |
| topic | per-fluorinated organic polymers nucleophilic aromatic substitution azomethine-based linkers azo-based linkers porosity measurements environmental applications |
| url | https://www.mdpi.com/2073-4360/15/20/4191 |
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