A CO2-switchable amidine monomer: synthesis and characterization
Smart system employed CO2 gas as new trigger has been attracting enormous attention in recent years, but few monomers that are capable of switching their hydrophobicity/hydrophility upon CO2 stimulation have been reported. A novel CO2 responsive monomer, 4-vinylbenzyl amidine, is designed and synthe...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Taylor & Francis Group
2017-01-01
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| Series: | Designed Monomers and Polymers |
| Subjects: | |
| Online Access: | http://dx.doi.org/10.1080/15685551.2016.1270027 |
| _version_ | 1818158946752397312 |
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| author | Hanbin Liu Hongyao Yin Yujun Feng |
| author_facet | Hanbin Liu Hongyao Yin Yujun Feng |
| author_sort | Hanbin Liu |
| collection | DOAJ |
| description | Smart system employed CO2 gas as new trigger has been attracting enormous attention in recent years, but few monomers that are capable of switching their hydrophobicity/hydrophility upon CO2 stimulation have been reported. A novel CO2 responsive monomer, 4-vinylbenzyl amidine, is designed and synthesized in this work with N,N-dimethylacetamide dimethyl acetal and 4-vinylbenzyl amine that is prepared through the Gabriel reaction. In bi-phase solvent of n-hexane and water, the monomer dissolves in n-hexane first and then transforms into water upon the CO2 treatment, indicating a hydrophobic to hydrophilic transition. This transformation is demonstrated as reversible by monitoring the conductivity variation of its wet dimethyl formamide solution during alternate bubbling/removing CO2. The protonation of 4-vinylbenzyl amidine upon CO2 treatment is demonstrated by 1H NMR which also accounts for the dissolubility change. The reversible addition-fragmentation chain-transfer polymerization of this monomer is also performed, finding the reaction only occurs in glacial acetic acid. The reason can be ascribed to the different radical structure produced in different solvent. |
| first_indexed | 2024-12-11T15:38:10Z |
| format | Article |
| id | doaj.art-b491ed3d68c141eb80aa76d68785d9b8 |
| institution | Directory Open Access Journal |
| issn | 1568-5551 |
| language | English |
| last_indexed | 2024-12-11T15:38:10Z |
| publishDate | 2017-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Designed Monomers and Polymers |
| spelling | doaj.art-b491ed3d68c141eb80aa76d68785d9b82022-12-22T00:59:53ZengTaylor & Francis GroupDesigned Monomers and Polymers1568-55512017-01-0120136336710.1080/15685551.2016.12700271270027A CO2-switchable amidine monomer: synthesis and characterizationHanbin Liu0Hongyao Yin1Yujun Feng2Chinese Academy of SciencesPolymer Research Institute, Sichuan UniversityChinese Academy of SciencesSmart system employed CO2 gas as new trigger has been attracting enormous attention in recent years, but few monomers that are capable of switching their hydrophobicity/hydrophility upon CO2 stimulation have been reported. A novel CO2 responsive monomer, 4-vinylbenzyl amidine, is designed and synthesized in this work with N,N-dimethylacetamide dimethyl acetal and 4-vinylbenzyl amine that is prepared through the Gabriel reaction. In bi-phase solvent of n-hexane and water, the monomer dissolves in n-hexane first and then transforms into water upon the CO2 treatment, indicating a hydrophobic to hydrophilic transition. This transformation is demonstrated as reversible by monitoring the conductivity variation of its wet dimethyl formamide solution during alternate bubbling/removing CO2. The protonation of 4-vinylbenzyl amidine upon CO2 treatment is demonstrated by 1H NMR which also accounts for the dissolubility change. The reversible addition-fragmentation chain-transfer polymerization of this monomer is also performed, finding the reaction only occurs in glacial acetic acid. The reason can be ascribed to the different radical structure produced in different solvent.http://dx.doi.org/10.1080/15685551.2016.1270027CO2-switchablesmart polymermonomersynthesisstimuli-responsive |
| spellingShingle | Hanbin Liu Hongyao Yin Yujun Feng A CO2-switchable amidine monomer: synthesis and characterization Designed Monomers and Polymers CO2-switchable smart polymer monomer synthesis stimuli-responsive |
| title | A CO2-switchable amidine monomer: synthesis and characterization |
| title_full | A CO2-switchable amidine monomer: synthesis and characterization |
| title_fullStr | A CO2-switchable amidine monomer: synthesis and characterization |
| title_full_unstemmed | A CO2-switchable amidine monomer: synthesis and characterization |
| title_short | A CO2-switchable amidine monomer: synthesis and characterization |
| title_sort | co2 switchable amidine monomer synthesis and characterization |
| topic | CO2-switchable smart polymer monomer synthesis stimuli-responsive |
| url | http://dx.doi.org/10.1080/15685551.2016.1270027 |
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