Oxygen and carbon dioxide dual gas-responsive homopolymers and diblock copolymers synthesized via RAFT polymerization
The monomer, 2,2,2-trifluoroethyl 3-( N -(2-(diethylamino)ethyl)acrylamido)propanoate (TF-DEAE-AM), which contains both O 2 and CO 2 -responsive functionalities, was first synthesized from commercially available N , N -diethylethylenediamine, 2,2,2-trifluoroethyl acrylate, and acryloyl chloride. Sub...
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Veröffentlicht in: | Polymer chemistry 2017-02, Vol.8 (7), p.1163-1176 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The monomer, 2,2,2-trifluoroethyl 3-(
N
-(2-(diethylamino)ethyl)acrylamido)propanoate (TF-DEAE-AM), which contains both O
2
and CO
2
-responsive functionalities, was first synthesized from commercially available
N
,
N
-diethylethylenediamine, 2,2,2-trifluoroethyl acrylate, and acryloyl chloride. Subsequently, a series of dual-gas responsive polymers, poly(2,2,2-trifluoroethyl 3-(
N
-(2-(diethylamino)ethyl)acrylamido)propanoate) (poly(TF-DEAE-AM)) and poly(ethylene glycol)-
b
-poly(2,2,2-trifluoroethyl 3-(
N
-(2-(diethylamino)ethyl)acrylamido)propanoate) (PEG-
b
-poly(TF-DEAE-AM)), were synthesized by employing reversible addition–fragmentation chain transfer (RAFT) polymerization. Due to the protonation between CO
2
and DEAE groups, and the specific van der Waals interactions between O
2
and C–F bonds, micelles consisting of poly(TF-DEAE-AM) or PEG-
b
-poly(TF-DEAE-AM) display distinct CO
2
and O
2
responsiveness in aqueous media. Pyrene, which is a model hydrophobic drug, is able to be effectively encapsulated in the micelles based on PEG-
b
-poly(TF-DEAE-AM). It is found that the release of pyrene sharply increases after bubbling CO
2
or O
2
compared to N
2
, and the release rate of the solution bubbling with CO
2
is the fastest. Since both CO
2
and O
2
are key gases for the human body, the CO
2
- and O
2
-induced release property of poly(TF-DEAE-AM) may open opportunities for the preparation of functional materials with special CO
2
and O
2
responsiveness for potential applications in biomedicine. |
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ISSN: | 1759-9954 1759-9962 |
DOI: | 10.1039/C6PY02004F |