Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 34, Pages 9849-9852Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503489
Keywords
alkanes; crystals; host-guest chemistry; macrocyclic compound; pillar[n]arenes
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Funding
- JSPS KAKENHI [15H00990]
- Kanazawa University CHOZEN Project
- Grants-in-Aid for Scientific Research [15H00990, 26810050, 26620097, 25708022] Funding Source: KAKEN
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Activated perethylated pillar[5]arene crystals show an unexpected alkane-shape-and -length-selective gate-opening behavior. Activated crystals were obtained upon removing solvents from perethylated pillar[5]arene crystals by heating. The activated crystals could quantitatively take up n-alkanes with carbon chains containing more than five carbon atoms as a consequence of their gate-opening pressure. As the chain length of the n-alkanes increased, the gate pressure decreased. A transformation into a herringbone structure was induced when n-hexane was used as a guest. By contrast, cyclic and branched alkanes were not taken up and could not induce a crystal transformation because they were too large to fit in the cavities of the pillar[5]arene. Alkane-shape-selective molecular recognition of pillar[5]arenes in the solution state was translated into the vapor/crystal state.
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