%AWang, Chao [Department of Chemistry University of Virginia Charlottesville VA 22904 USA]%AWang, Chao [Department of Chemistry; University of Virginia; Charlottesville VA 22904 USA]%AWu, Xuedan [Department of Chemistry University of Virginia Charlottesville VA 22904 USA]%AWu, Xuedan [Department of Chemistry; University of Virginia; Charlottesville VA 22904 USA]%APu, Lin [Department of Chemistry University of Virginia Charlottesville VA 22904 USA]%APu, Lin [Department of Chemistry; University of Virginia; Charlottesville VA 22904 USA]%BJournal Name: Chemistry – A European Journal; Journal Volume: 23; Journal Issue: 45; Related Information: CHORUS Timestamp: 2023-09-14 01:48:05 %D2017%IWiley Blackwell (John Wiley & Sons) %JJournal Name: Chemistry – A European Journal; Journal Volume: 23; Journal Issue: 45; Related Information: CHORUS Timestamp: 2023-09-14 01:48:05 %K %MOSTI ID: 10032402 %PMedium: X %TA Highly Fluorinated Chiral Aldehyde for Enantioselective Fluorescent Recognition in a Biphasic System %XAbstract

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 oftrans‐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.

%0Journal Article