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Diversity‐Oriented Construction and Interconversion of Multicavity Supermacrocycles for Cooperative Anion–π Binding
Author(s) -
Luo Jian,
Ao YuFei,
Wang QiQiang,
Wang DeXian
Publication year - 2018
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.201810836
Subject(s) - triazine , chemistry , ion , base (topology) , stereochemistry , crystallography , combinatorial chemistry , polymer chemistry , organic chemistry , mathematics , mathematical analysis
A one‐pot strategy for the diverse construction of a series of supermacrocycles was realized using rationally designed macrocyclic precursors. The base was found to have a significant effect not only on the size distribution but also on the structure of the supermacrocycles formed. While the use of less CsF (<4.0 equiv) afforded regular supermacrocycles containing up to four macrocyclic precursor subunits, the use of more CsF (>8.0 equiv) resulted in structurally reorganized supermacrocyles featuring oxacalix[2]arene[2]triazine motifs. Base‐mediated supermacrocycle‐to‐supermacrocycle transformations were also revealed. With large cavities and many electron‐deficient triazine moieties, the supermacrocyles can accommodate large organic anions via multiple anion–π interactions as demonstrated for two supermacrocycles, which can host 2‐carboxyacetate and represent the first crystallographic examples of sandwich‐like structures with anion–π interactions.