Enhanced Enantioselectivity in the Fluorescent Recognition of a Chiral Diamine by Using a Bisbinaphthyl Dialdehyde

Chaoyuan Zeng; Xiaoling Zhang; Lin Pu

doi:10.1021/acsomega.8b01870

Enhanced Enantioselectivity in the Fluorescent Recognition of a Chiral Diamine by Using a Bisbinaphthyl Dialdehyde

Chaoyuan Zeng, Xiaoling Zhang^*, Lin Pu

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A bisbinaphthyl dialdehyde shows greatly enhanced enantioselective fluorescent response (ef = 10.0) in the fluorescent recognition of a chiral diamine, 1,2-diphenylethylenediamine, over a previously reported monobinaphthyl dialdehyde (ef = 1.1). This compound can be used to determine the enantiomeric composition of the diamine by fluorescence measurement. The NMR and mass spectroscopic studies have demonstrated that the chirality matched reaction of the bisbinaphthyl dialdehyde with the diamine in the presence of Zn(OAc)₂ favors the formation of a macrocyclic product more than the chirality mismatched. This enantioselective cyclocondensation should contribute to the observed highly enantioselective fluorescent response because the macrocyclic Zn(II) complex is proposed to give much greater fluorescence enhancement than the acyclic ones.

Original language	English
Pages (from-to)	12545-12548
Number of pages	4
Journal	ACS Omega
Volume	3
Issue number	10
DOIs	https://doi.org/10.1021/acsomega.8b01870
Publication status	Published - 31 Oct 2018

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title = "Enhanced Enantioselectivity in the Fluorescent Recognition of a Chiral Diamine by Using a Bisbinaphthyl Dialdehyde",

abstract = "A bisbinaphthyl dialdehyde shows greatly enhanced enantioselective fluorescent response (ef = 10.0) in the fluorescent recognition of a chiral diamine, 1,2-diphenylethylenediamine, over a previously reported monobinaphthyl dialdehyde (ef = 1.1). This compound can be used to determine the enantiomeric composition of the diamine by fluorescence measurement. The NMR and mass spectroscopic studies have demonstrated that the chirality matched reaction of the bisbinaphthyl dialdehyde with the diamine in the presence of Zn(OAc)2 favors the formation of a macrocyclic product more than the chirality mismatched. This enantioselective cyclocondensation should contribute to the observed highly enantioselective fluorescent response because the macrocyclic Zn(II) complex is proposed to give much greater fluorescence enhancement than the acyclic ones.",

author = "Chaoyuan Zeng and Xiaoling Zhang and Lin Pu",

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T1 - Enhanced Enantioselectivity in the Fluorescent Recognition of a Chiral Diamine by Using a Bisbinaphthyl Dialdehyde

AU - Zeng, Chaoyuan

AU - Zhang, Xiaoling

AU - Pu, Lin

PY - 2018/10/31

Y1 - 2018/10/31

N2 - A bisbinaphthyl dialdehyde shows greatly enhanced enantioselective fluorescent response (ef = 10.0) in the fluorescent recognition of a chiral diamine, 1,2-diphenylethylenediamine, over a previously reported monobinaphthyl dialdehyde (ef = 1.1). This compound can be used to determine the enantiomeric composition of the diamine by fluorescence measurement. The NMR and mass spectroscopic studies have demonstrated that the chirality matched reaction of the bisbinaphthyl dialdehyde with the diamine in the presence of Zn(OAc)2 favors the formation of a macrocyclic product more than the chirality mismatched. This enantioselective cyclocondensation should contribute to the observed highly enantioselective fluorescent response because the macrocyclic Zn(II) complex is proposed to give much greater fluorescence enhancement than the acyclic ones.

AB - A bisbinaphthyl dialdehyde shows greatly enhanced enantioselective fluorescent response (ef = 10.0) in the fluorescent recognition of a chiral diamine, 1,2-diphenylethylenediamine, over a previously reported monobinaphthyl dialdehyde (ef = 1.1). This compound can be used to determine the enantiomeric composition of the diamine by fluorescence measurement. The NMR and mass spectroscopic studies have demonstrated that the chirality matched reaction of the bisbinaphthyl dialdehyde with the diamine in the presence of Zn(OAc)2 favors the formation of a macrocyclic product more than the chirality mismatched. This enantioselective cyclocondensation should contribute to the observed highly enantioselective fluorescent response because the macrocyclic Zn(II) complex is proposed to give much greater fluorescence enhancement than the acyclic ones.

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Enhanced Enantioselectivity in the Fluorescent Recognition of a Chiral Diamine by Using a Bisbinaphthyl Dialdehyde

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