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Synthesis of i ‐Corona[6]arenes for Selective Anion Binding: Interdependent and Synergistic Anion–π and Hydrogen‐Bond Interactions
Author(s) -
Zhuang ShengYi,
Cheng Ying,
Zhang Qian,
Tong Shuo,
Wang MeiXiang
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008997
Subject(s) - tetrazine , chemistry , resorcinol , hydrogen bond , nucleophile , ion , medicinal chemistry , nucleophilic aromatic substitution , nucleophilic substitution , aryl , stereochemistry , crystallography , molecule , organic chemistry , alkyl , catalysis
i‐Corona[3]arene[3]tetrazines were synthesized from the nucleophilic aromatic substitution reaction of resorcinol and its derivatives with 3,6‐dichlorotetrazine in a one‐pot fashion under mild conditions. All of the resulting macrocycles adopted 1,3,5‐alternate conformation irrespective of the nature of the substituents on both upper‐ and lower‐rims. i‐Corona[3]arene[3]tetrazine was found to self‐regulate its macrocyclic conformation and cavity to recognize anions with binding constants spanning from 26 M −1 to 2.2×10 3 M −1 depending on the structure of the anions. The selective binding resulted from a significant interdependent and synergistic effect between multiple tetrazine π/anion and C aryl –H/anion hydrogen bond interactions. Taking advantage of synergistic effect revealed, a cyanobenzene‐embedded i‐corona[3]arene[3]tetrazine was designedly synthesized and highly selective and very strong affinity toward nitrate with a binding constant of 2.2×10 5 M −1 was achieved.