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dc.contributor.authorHo, I-Tingen_US
dc.contributor.authorChu, Jean-Hoen_US
dc.contributor.authorChung, Wen-Shengen_US
dc.date.accessioned2014-12-08T15:12:02Z-
dc.date.available2014-12-08T15:12:02Z-
dc.date.issued2011-03-01en_US
dc.identifier.issn1434-193Xen_US
dc.identifier.urihttp://dx.doi.org/10.1002/ejoc.201001169en_US
dc.identifier.urihttp://hdl.handle.net/11536/9228-
dc.description.abstractWe report herein the synthesis of a fluorescence turn-on chemosensor, 25,27-bis{N-[1-(4-{[4-amino-4-(1-naphthyl)-2oxo- 3-butenyl]oxy}phenyl)aminocarbonyl]methoxy}-26,28-dihydroxycalix[4]arene (3b), which is highly selective toward Cu(2+). The fluorescence intensity of 3b was enhanced upon adding [Cu(ClO(4))(2)], which reached a maximum with approximately 4 equiv. of Cu(2+) but then started to decrease in intensity at higher Cu(2+) concentrations. Job plot experiments revealed a 1:2 binding stoichiometry of 3b with Cu(2+). Based on (1)H NMR titration results, we infer that there are two possible binding sites for Cu(2+) in 3b: one at the lower-rim phenolic-OH and amide groups, and the second at the beta-amino alpha,beta-unsaturated ketone groups. It is important to note that during the complexation of 3b with [Cu(ClO(4))(2)], the Cu(2+) ions were reduced to Cu(+) by both the phenolic OH and the amines of the beta-amino alpha,beta-unsaturated ketones. Furthermore, control compounds 6 and 9b were synthesized to clarify the possible binding sites of Cu(2+) in 3b. By comparing the binding constants of 3b, 6, and 9b with Cu(2+), we found that 3b exhibited a positive allosteric behavior toward the coordination of two Cu(2+) ions.en_US
dc.language.isoen_USen_US
dc.subjectFluorescenceen_US
dc.subjectIonophoresen_US
dc.subjectSensorsen_US
dc.subjectSupramolecular chemistryen_US
dc.subjectCopperen_US
dc.subjectUVen_US
dc.subjectVis spectroscopyen_US
dc.titleCalix[4]arene with Lower-Rim beta-Amino alpha,beta-Unsaturated Ketones Containing Bis-Chelating Sites as a Highly Selective Fluorescence Turn-On Chemosensor for Two Copper(II) Ionsen_US
dc.typeArticleen_US
dc.identifier.doi10.1002/ejoc.201001169en_US
dc.identifier.journalEUROPEAN JOURNAL OF ORGANIC CHEMISTRYen_US
dc.citation.volumeen_US
dc.citation.issue8en_US
dc.citation.spage1472en_US
dc.citation.epage1481en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000288129100010-
dc.citation.woscount11-
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