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Greatly Enhanced Fluorescence by Increasing the Structural Rigidity of an Imine: Enantioselective Recognition of 1,2‐Cyclohexanediamine by a Chiral Aldehyde
Author(s) -
Xu Yimang,
Yu Shanshan,
Chen Qi,
Chen Xuemin,
Xiao Meng,
Chen Liming,
Yu Xiaoqi,
Xu Yong,
Pu Lin
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504686
Subject(s) - aldehyde , diamine , imine , enantioselective synthesis , chemistry , acryloyl chloride , fluorescence , chelation , combinatorial chemistry , organic chemistry , catalysis , polymer , copolymer , physics , quantum mechanics , acrylate
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 λ =410 nm 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.