Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 38, Pages 11360-11364Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703357
Keywords
acridinium; dynamic motions; host-guest complexes; macrocycles; pH-responsive molecules
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Funding
- JSPS KAKENHI [JP25104011/JP26288033/JP17H05359]
- Support for Tokyotech Advanced Researchers (STAR)
- Grants-in-Aid for Scientific Research [16K13947, 25104011] Funding Source: KAKEN
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In spite of wide-ranging previous studies on synthetic macrocycles, the installation of open-close functions into the frameworks remains a challenge. We present a new polyaromatic macrocycle capable of switching between open and closed forms in response to external stimuli, namely, base and acid. The macrocycle, which is prepared in three steps, has a well-defined hydrophobic cavity with a length of around 1 nm, surrounded by four pH-responsive acridinium panels. The open and closed structures were confirmed by single-crystal X-ray analysis. The cylindrical cavity can bind long hydrophilic molecules up to 2.7 nm in length in neutral water and then release the bound guests through a reversible open-to-closed structural change upon simple addition of base.
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