Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 1860-1867Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2024448
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Funding
- National Natural Science Foundation of China [20875094, 21072197, 20972161, 21121004, 21132005]
- Ministry of Sciences and Technology [2011CB932501, 2007CB808005]
- Chinese Academy of Sciences
- Tsinghua University
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Novel macrocyclic anion receptors based on the principle of anion-pi interactions were reported. By means of both post-macrocyclization modification protocol and the stepwise fragment coupling approach, functionalized oxacalix[2]arene[2]triazines bearing two other electron-deficient (hetero)aromatic rings on the lower rim were efficiently synthesized. The resulting oxacalix[2]arene[2]triazine macrocycles adopt 1,3-alternate conformation, yielding therefore an expanded electron-deficient cavity or space consisting of two triazine rings and two appending aromatic rings. Spectroscopic titration study showed the selective interaction of the pentafluorophenyl-substituted oxacalix[2]arene[2]triazine with azide and fluoride in solution with the binding constants (K-1:1) ranging from 1.33 x 10(3) to 3.52 x 10(3) M-1.
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