期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 17, 页码 5963-5968出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504686
关键词
BINOL; chiral amine; chiral recognition; fluorescence sensor; imine
资金
- National Science Foundation of China [21502127, 21321061, J1103315, J1310008]
- National Program on Key Basic Research Project of China(973 Program) [2013CB328905]
An aldehyde that is not fluorescent responsive toward a chiral diamine has been converted to a sensitive fluorescence enhancement sensor through incorporation of an additional hydrogen bonding unit to increase the structural rigidity of the reaction product of the aldehyde with the diamine. This new chiral aldehyde is synthesized in one step from the reaction of (S)-3-formylBINOL with salicyl chloride. When treated with trans-1,2-cyclohexanediamine in ethanol, it shows greatly enhanced fluorescence at =410nm with good enantioselectivity. NMR and mass spectroscopic methods are used to investigate the reaction of the chiral aldehyde with the diamine. This study has revealed a two-stage reaction mechanism including a fast imine formation and a slow ester cleavage.
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