Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 45, Pages 10749-10752Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201702354
Keywords
aldehydes; BINOL; chiral amines; enantioselectivity; fluorescence; fluorous phase
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Funding
- US National Science Foundation [CHE-1565627]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1565627] Funding Source: National Science Foundation
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A 1,1'-bi-2-naphthol (BINOL)-based aldehyde containing four perfluoroalkyl groups has been designed and synthesized. It shows enantioselective fluorescence enhancement at 420 nm when treated with the enantiomers of trans-1,2-diaminocyclohexane in an organic/fluorous biphasic system. The enantiomeric excess of the diamine in methanol can be linearly correlated with the emission intensity of of the aldehyde in perfluorohexane (FC-72). This is the first example to determine the enantiomeric composition of a chiral molecule by using a fluorescent sensor in a fluorous/organic biphasic system. The mechanism of the reaction was investigated by NMR spectroscopy and mass spectrometry.
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