Greatly Enhanced Fluorescence by Increasing the Structural Rigidity of an Imine: Enantioselective Recognition of 1,2-Cyclohexanediamine by a Chiral Aldehyde

Yimang Xu; Shanshan Yu; Qi Chen; Xuemin Chen; Meng Xiao; Liming Chen; Xiaoqi Yu; Yong Xu; Lin Pu

doi:10.1002/chem.201504686

Greatly Enhanced Fluorescence by Increasing the Structural Rigidity of an Imine: Enantioselective Recognition of 1,2-Cyclohexanediamine by a Chiral Aldehyde

Chemistry. 2016 Apr 18;22(17):5963-8. doi: 10.1002/chem.201504686. Epub 2016 Mar 16.

Authors

Yimang Xu¹, Shanshan Yu², Qi Chen¹, Xuemin Chen¹, Meng Xiao¹, Liming Chen¹, Xiaoqi Yu³, Yong Xu⁴, Lin Pu^{5

6}

Affiliations

¹ Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
² Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. yushanshan@scu.edu.cn.
³ Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. xqyu@scu.edu.cn.
⁴ Humanwell Healthcare (Group) Co., LTD., 666 Gaoxin Road, East High-Tech Development Zone, Wuhan, Hubei, 430075, P. R. China.
⁵ Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China. lp6n@virginia.edu.
⁶ Department of Chemistry, University of Virginia, McCormick Rd, Charlottesville, VA, 22904, USA. lp6n@virginia.edu.

PMID: 26991951
DOI: 10.1002/chem.201504686

Abstract

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.

Keywords: BINOL; chiral amine; chiral recognition; fluorescence sensor; imine.

Publication types

Research Support, Non-U.S. Gov't