Host–Guest Complexation of Perethylated Pillararene with Alkanes in the Crystal State

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 wit...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-08, Vol.54 (34), p.9849-9852
Main Authors: Ogoshi, Tomoki, Sueto, Ryuta, Yoshikoshi, Kumiko, Sakata, Yoko, Akine, Shigehisa, Tada‐aki Yamagishi
Format: Article
Language:English
Subjects:
Activated carbon
Alkanes
Aromatic compounds
Crystals
Hexanes
Molecular chains
Shape recognition
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201503489