Synthetic macrocyclic host molecules always play an essential role in the establishment and development of supramolecular chemistry. Along with the continuous interests in the study of classical macrocycles, recent decades have witnessed the emergence and rapid development of the chemistry and supramolecular chemistry of novel and functional macrocycles. Owing to their easy availability, a self-tunable V-shaped cavity resulted from 1,3-alternate conformation, and diversified electronic features steered by the interplay between heteroatom linkages and aromatic rings, heteracalixaromatics act as a type of versatile and powerful macrocyclic hosts in molecular recognition and fabrication of supramolecular systems. Very recently, by means of engineering the bond connectivity or the recombination of chemical bonds within heteracalixaromatics, we have devised coronarenes, a new generation of macrocycles. In this concise review, macrocyclic and supramolecular chemistry of coronarenes are summarized in the order of their syntheses, structural features, molecular recognition and self-assembly properties. In the last part of this article, personal perspectives on the study of macrocyclic and supramolecular chemistry will also be discussed.
the National Natural Science Foundation of China(21732004,21421064,91427301,21132005)
Tsinghua University.
This work was supported by the National Natural Science Foundation of China (21732004, 21421064, 91427301, 21132005) and Tsinghua University. I am indebted to talented research students and postdoctoral fellows, whose names can be found in references, for their great contributions to the project of macrocyclic and supramolecular chemistry.
The author declares no conflict of interest.
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Figure 1
General structure of heteracalixaromatics (color online).
Figure 2
General structure of coronarenes (color online).
Figure 3
The one-pot reaction method for the synthesis of oxygen and sulfur linked corona
Figure 4
Synthesis of corona[4]arene[2]tetrazines from one-pot reaction (color online).
Figure 5
One-pot three-component reaction for the synthesis corona[3]arene[2]tetrazines (color online).
Figure 6
The fragment coupling approach to corona[4]arene[2]tetrazines (color online).
Figure 7
Synthesis of corona[5]arenes from corona[6]arenes through macrocycle-to-macrocycle transformation (color online).
Figure 8
Synthesis of corona[3]arene[3]pyridazines from inverse electron demand Diels-Alder reaction of corona[3]arene[3]tetrazines (color online).
Figure 9
Synthesis of sulfone and sulphide linked corona[4]arene[2]pyridazines from selective oxidation of sulphide (color online).
Figure 10
Synthesis of functionalized coronarenes via functional group transformations (color online).
Figure 11
Some representative X-ray molecular structures of corona[6]arenes with top and side views. Substituents are hidden for clarity (color online).
Figure 12
X-ray molecular structures of corona[5]arenes with top and side views (color online).
Figure 13
Partial variable temperature 1H NMR (a) and 13C NMR (b, c (expanded)) spectra of
Figure 14
X-ray molecular structure of the complex between coronarene
Figure 15
X-ray molecular structure of complex between coronarene
Figure 16
X-ray molecular structure of complex between coronarene and 1,4-dibenzyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium hexafluorophosphate. Cation and solvent molecules are omitted for clarity (color online).
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