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- Title
Efficient and Regioselectivity-Tunable Metal-Free Polycycloaddition of Activated Azide and Alkynes.
- Authors
Wu, Yongwei; He, Benzhao; Wang, Jia; Hu, Rongrong; Zhao, Zujin; Huang, Fei; Qin, Anjun; Tang, Ben Zhong
- Abstract
The transition-metal catalyzed and metal-free click polymerizations have been developed as powerful tools for the construction of functional polymers with linear and hyperbranched structures. The latter provides a thorough solution for the completely removing metallic residues from the products encountered in the former. Compared to the activated alkyne-azide metal-free click polymerization, the activated azide-alkyne one is rarely studied. In this Communication, a perfluorophenyl-activated azide of hexane-1,6-diyl-bis(4-azido-2,3,5,6-tetrafluorobenzoate) is rationally designed and facilely prepared. Through systematical optimization of the reaction conditions, an efficient metal-free perfluorophenylazide-alkyne polycycloaddition is established, and polytriazoles with high molecular weights (up to 166 000) and excellent solubility are obtained in excellent yields (up to 93%) under mild reaction conditions. Interestingly, the regioselectivity of the reaction could be fine-tuned by the solvents and diyne monomers. Therefore, this work provides not only a powerful tool for the preparation of functional polytriazoles, but also an attractive method for fine-tuning their regioregularity.
- Subjects
REGIOSELECTIVITY (Chemistry); STEREOCHEMISTRY; HEXANE; ALIPHATIC hydrocarbons; POLYTRICHACEAE
- Publication
Macromolecular Rapid Communications, 2017, Vol 38, Issue 4, pn/a
- ISSN
1022-1336
- Publication type
Article
- DOI
10.1002/marc.201600620