期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 16, 期 1, 页码 49-55出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202001154
关键词
supramolecular chemistry; host-guest systems; molecular recognition; helicate; chirality
资金
- JSPS KAKENHI [JP17H05375, JP19H04585, JP17H05159]
- Adaptable and Seamless Technology transfer Program through Target-driven R&D (A-STEP) from Japan Science and Technology Agency (JST)
- Ogasawara Foundation for the Promotion of Science Engineering
- Nippon Sheet Glass Foundation
- Iketani Science and Technology Foundation
- Takahashi Industrial and Economic Research Foundation
- Fukuoka Naohiko Memorial Foundation
In this study, a triple-stranded metallohelicate was formed by self-assembly of 5,17-difunctionalized calix[4]arenes and metal cations, showing good encapsulation properties and selectivity. CD spectroscopy confirmed the preference of the metallohelicate for guest molecules. NMR, UV-vis experiments, and molecular mechanics calculations revealed the interaction mechanism between the metallohelicate and guest molecules.
The title complex is a triple-stranded metallohelicate organized by the self-assembly of 5,17-difunctionalized calix[4]arenes and metal cations with octahedral coordination geometry. Due to hydrophilic triethylene glycol chains on the lower rim of the calix[4]arene, the metallohelicate can encapsulate cationic guests in water. NMR and UV-vis titration experiments reveal that the metallohelicate captures a pyridinium guest with an alanine derivative to form a host-guest complex with a host-guest ratio of 1 : 1. CD spectroscopy confirms the bias of the P- and M-helical sense of the metallohelicate by the captured guest. The metallohelicate captures two molecules of dicationic N,N'-dimethyl-DABCO and monocationic N-methyl quinuclidine, exhibiting a positive allosteric effect. H-1 NMR titration experiments indicate that the bound guests are in close proximately to the aromatic rings of the ligands. Molecular mechanics calculations based on the UV-vis and NMR observations suggest that the first guest preorganizes the conformation of the metallohelicate to facilitate access of the second guest to the cavity.
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