Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction
Abstract
:1. Introduction
2. Experimental
2.1. Materials
2.2. Measurements
2.3. Synthesis of Intermediates and Monomers (Scheme 1)
2.3.1. Synthesis of 3,6-Dibromo-9-(4-vinylbenzyl)-9H-carbazole (1)
2.3.2. Synthesis of 4’-(3,5-Dibromophenyl)-2,2’:6’,2’’-terpyridine (3)
2.3.3. Synthesis of 4′-(4,4″-Divinyl-[1,1′:3′,1″-terphenyl]-5′-yl)-2,2′:6′,2″-terpyridine (4)
2.4. Synthesis of Polymers (Scheme 2)
2.4.1. Synthesis of Carbazole-Functionalized Polymer (PC2Br) Using the RAFT Method
2.4.2. Synthesis of Carbazole-Functionalized Copolymer (PCaT) Using the Heck Method
2.5. Fluorescent Titration with Metal Ions
2.6. Preparation of Micellar Aggregates
3. Results and Discussion
3.1. Synthesis of Intermediates and Monomers
3.2. Synthesis and Thermal Properties of Polymers
3.3. Optical Properties of Polymers
3.4. Ion Sensing Properties
3.5. Self-Assembly of Polymer in THF Solution
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Polymer | Yield (%) | Mw (×103) a | PDI a | Tg (°C) b | Td (°C) c | Molar ratio (x:y) d |
---|---|---|---|---|---|---|
PC2Br | 18.4 | 6.78 | 1.12 | 186.6 | 314.3 | ― |
PCaT | 10.3 | 7.92 | 1.14 | 198.3 | 343.0 | 94:6 |
PCT | 35.6 | 12.2 | 1.65 | 159.8 | 268.7 | 55:45 |
Polymer | UV-vis λmax sol’n (nm) a | UV-vis λmax film (nm) a | PL λmax sol’n (nm) b | PL λmax film (nm) b | Stokes shift c | ΦPL d |
---|---|---|---|---|---|---|
PCaT | 271, 346s | 293, 350s | 381 | 394 | 110 | 0.062 |
PCT | 232, 275s | 297 | 391 | 428, 529s | 159 | 0.51 |
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Yang, P.-C.; Li, S.-Q.; Chien, Y.-H.; Tao, T.-L.; Huang, R.-Y.; Chen, H.-Y. Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction. Polymers 2017, 9, 427. https://doi.org/10.3390/polym9090427
Yang P-C, Li S-Q, Chien Y-H, Tao T-L, Huang R-Y, Chen H-Y. Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction. Polymers. 2017; 9(9):427. https://doi.org/10.3390/polym9090427
Chicago/Turabian StyleYang, Po-Chih, Si-Qiao Li, Yueh-Han Chien, Ta-Lun Tao, Ruo-Yun Huang, and Hsueh-Yu Chen. 2017. "Synthesis, Chemosensory Properties, and Self-Assembly of Terpyridine-Containing Conjugated Polycarbazole through RAFT Polymerization and Heck Coupling Reaction" Polymers 9, no. 9: 427. https://doi.org/10.3390/polym9090427