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Modulating the Binding of Polycyclic Aromatic Hydrocarbons Inside a Hexacationic Cage by Anion-π Interactions.
- Source :
-
Angewandte Chemie International Edition . Jan2015, Vol. 54 Issue 2, p456-461. 6p. - Publication Year :
- 2015
-
Abstract
- We report the template-directed synthesis of BlueCage6+, a macrobicyclic cyclophane composed of six pyridinium rings fused with two central triazines and bridged by three paraxylylene units. These moieties endow the cage with a remarkably electron-poor cavity, which makes it a powerful receptor for polycyclic aromatic hydrocarbons (PAHs). Upon forming a 1:1 complex with pyrene in acetonitrile, however, BlueCage⋅6 PF6 exhibits a lower association constant Ka than its progenitor ExCage⋅6 PF6. A close inspection reveals that the six PF6− counterions of BlueCage6+ occupy the cavity in a fleeting manner as a consequence of anion-π interactions and, as a result, compete with the PAH guests. This conclusion is supported by a one order of magnitude increase in the Ka value for pyrene in BlueCage6+ when the PF6− counterions are replaced by much bulkier anions. The presence of anion-π interactions is supported by X-ray crystallography, and confirms the presence of a PF6− counterion inside its cavity. [ABSTRACT FROM AUTHOR]
- Subjects :
- *AROMATIC compounds
*MOLECULAR interactions
*TRIAZENES
*ACETONITRILE
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 54
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 100238118
- Full Text :
- https://doi.org/10.1002/anie.201408400