Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 윤주영 | * |
dc.date.accessioned | 2016-08-28T12:08:18Z | - |
dc.date.available | 2016-08-28T12:08:18Z | - |
dc.date.issued | 2011 | * |
dc.identifier.issn | 0947-6539 | * |
dc.identifier.other | OAK-7347 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/221423 | - |
dc.description.abstract | Intermolecular interactions that involve aromatic rings are key processes in both chemical and biological recognition. It is common knowledge that the existence of anion-π interactions between anions and electron-deficient (π-acidic) aromatics indicates that electron-rich (π-basic) aromatics are expected to be repulsive to anions due to their electron-donating character. Here we report the first concrete theoretical and experimental evidence of the anion-π interaction between electron-rich alkylbenzene rings and a fluoride ion in CH 3CN. The cyclophane cavity bridged with three naphthoimidazolium groups selectively complexes a fluoride ion by means of a combination of anion-π interactions and (CH) +⋯F --type ionic hydrogen bonds. 1H NMR, 19F NMR, and fluorescence spectra of 1 and 2 with fluoride ions are examined to show that only 2 can host a fluoride ion in the cavity between two alkylbenzene rings to form a sandwich complex. In addition, the cage compounds can serve as highly selective and ratiometric fluorescent sensors for a fluoride ion. With the addition of 1 equiv of F -, a strongly increased fluorescence emission centered at 385 nm appears at the expense of the fluorescence emission of 2 centered at 474 nm. Finally, isothermal titration calorimetry (ITC) experiments were performed to obtain the binding constants of the compounds 1 and 2 with F - as well as Gibbs free energy. The 2-F - complex is more stable than the 1-F - complex by 1.87 kcal mol -1, which is attributable to the stronger anion-π interaction between F - and triethylbenzene. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | * |
dc.language | English | * |
dc.title | Induction-driven stabilization of the anion-π interaction in electron-rich aromatics as the key to fluoride inclusion in imidazolium-cage receptors | * |
dc.type | Article | * |
dc.relation.issue | 4 | * |
dc.relation.volume | 17 | * |
dc.relation.index | SCI | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 1163 | * |
dc.relation.lastpage | 1170 | * |
dc.relation.journaltitle | Chemistry - A European Journal | * |
dc.identifier.doi | 10.1002/chem.201002105 | * |
dc.identifier.wosid | WOS:000287562300013 | * |
dc.identifier.scopusid | 2-s2.0-78751629926 | * |
dc.author.google | Xu Z. | * |
dc.author.google | Singh N.J. | * |
dc.author.google | Kim S.K. | * |
dc.author.google | Spring D.R. | * |
dc.author.google | Kim K.S. | * |
dc.author.google | Yoon J. | * |
dc.contributor.scopusid | 윤주영(7403587371) | * |
dc.date.modifydate | 20240118162450 | * |