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- Publisher Website: 10.1002/anie.201408400
- Scopus: eid_2-s2.0-84922721154
- WOS: WOS:000347238800009
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Article: Modulating the binding of polycyclic aromatic hydrocarbons inside a hexacationic cage by anion-π interactions
Title | Modulating the binding of polycyclic aromatic hydrocarbons inside a hexacationic cage by anion-π interactions |
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Authors | |
Keywords | Cage compounds Cyclophanes Host-guest complexes Supramolecular chemistry |
Issue Date | 2015 |
Citation | Angewandte Chemie - International Edition, 2015, v. 54, n. 2, p. 456-461 How to Cite? |
Abstract | We report the template-directed synthesis of Blue-Cage6+, 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·6PF6 exhibits a lower association constant Ka than its progenitor ExCage·6PF6. 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. |
Persistent Identifier | http://hdl.handle.net/10722/333104 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Hafezi, Nema | - |
dc.contributor.author | Holcroft, James M. | - |
dc.contributor.author | Hartlieb, Karel J. | - |
dc.contributor.author | Dale, Edward J. | - |
dc.contributor.author | Vermeulen, Nicolaas A. | - |
dc.contributor.author | Stern, Charlotte L. | - |
dc.contributor.author | Sarjeant, Amy A. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:16:46Z | - |
dc.date.available | 2023-10-06T05:16:46Z | - |
dc.date.issued | 2015 | - |
dc.identifier.citation | Angewandte Chemie - International Edition, 2015, v. 54, n. 2, p. 456-461 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10722/333104 | - |
dc.description.abstract | We report the template-directed synthesis of Blue-Cage6+, 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·6PF6 exhibits a lower association constant Ka than its progenitor ExCage·6PF6. 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. | - |
dc.language | eng | - |
dc.relation.ispartof | Angewandte Chemie - International Edition | - |
dc.subject | Cage compounds | - |
dc.subject | Cyclophanes | - |
dc.subject | Host-guest complexes | - |
dc.subject | Supramolecular chemistry | - |
dc.title | Modulating the binding of polycyclic aromatic hydrocarbons inside a hexacationic cage by anion-π interactions | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/anie.201408400 | - |
dc.identifier.scopus | eid_2-s2.0-84922721154 | - |
dc.identifier.volume | 54 | - |
dc.identifier.issue | 2 | - |
dc.identifier.spage | 456 | - |
dc.identifier.epage | 461 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:000347238800009 | - |