Study of the Zn<sup>II</sup>Complexes of 1,1′‐Binaphthyl‐Based Schiff Bases: Fluorescent Detection of Thiocyanate

Zhao, Haihang; Cao, Yuan; Zhang, Yanjing; Zhou, Yangyang; Zhao, Gang; Pu, Lin

doi:10.1002/ejic.201800479

Cited by 7 publications

(2 citation statements)

References 24 publications

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“…These dynamic amine exchange reactions have been used to afford an attractive way to develop enantioselective fluorescent recognition systems for chiral amines. In addition to these dynamic amine exchange reaction-based chiral recognition systems, other enantioselective fluorescent recognition systems have also been established by using chiral 1,1′-bi-2-naphthol-3-al or its derivatives to react with enantiomeric amines to create imines that enantioselectively coordinate with introduced Zn 2+ ions, resulting in enantiomeric discrimination in the fluorescence response. − Similar to reported dynamic amine exchange reaction-based fluorescent chiral recognition systems, the difference in the fluorescence response of these three-component systems − likely originates from different coordination stability constants of Zn 2+ –chiral imine complexes, or different modes of coordination between the Zn 2+ / d -configuration of imine and the Zn 2+ / l -configuration of imine, yet it is not easy to clarify the enantioselective fluorescence response mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Dynamic Exchange Reactions of Imines

Liu

Shen

2021

J. Org. Chem.

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Although dynamic reactions of imines have been extensively studied, the dynamic behaviors manipulated by chirality remain nearly unexplored. In this work, enantioselective amine exchange reactions were demonstrated as a first example via the reaction of enantiomeric chiral amines such as natural amino acids with a series of innovative axially chiral 1,1′-binaphthyl-2,2′-diamine (BNDA)-based imines that were prepared from the condensation reactions between BNDA and salicylaldehyde (SA) or its derivatives. This enantioselective dynamic behavior can be directly indicated by the degree of the fluorescence response of the R-configuration of imines to the D-enantiomer of chiral amine, because the released BNDA can serve as the fluorescence signal output when the amine exchange reaction occurs, which is far higher than the response to its L-enantiomer under identical experimental conditions. For the S-configuration of chiral imines, the fluorescence response is the opposite. The enantioselective exchange reaction can be tuned by altering the electron-withdrawing or electron-donating capability of the substituent at position 4 or 5 of the SA part of chiral imines. Not only o-OH groups in SA-based imines but also protic solvents used as reaction media were found to be important to the dynamic behavior at high rates.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Dynamic Exchange Reactions of Imines

Liu

Shen

2021

J. Org. Chem.

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“…Probes that form complexes with Zn(II) are used for the detection of other substances [27,[30][31][32][33]; 2. The probe directly recognizes Zn(II), leading to a change in fluorescence [34][35][36][37]. The probe we designed contains the BINAM structure and therefore may also have a certain recognition effect on Zn(II), potentially leading to an enhancement in fluorescence.…”

Section: The Effect Of Metal Ionsmentioning

confidence: 99%

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

Wu,

Lu,

Cai

et al. 2024

Preprint

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Lysine plays a crucial role in promoting development, enhancing immune function, and improving the function of central nervous system tissues. The two configurational isomers of amino acids have significantly different effects. Currently, methods for chiral recognition of lysine all have drawbacks such as expensive equipment and complicated detection processes, whereas fluorescence analysis boasts high sensitivity, strong selectivity, and simple operation. In this study, we synthesized four novel Binaphthyl-Amine (BINAM)-based fluorescent probes capable of specifically identifying the L-configuration of lysine among the twenty amino acids constituting human proteins. The enantiomeric fluorescence enhancement ratio (ef or ΔIL/ΔID) reached up to 15.29, demonstrating high enantioselectivity. We also evaluated the probe's recognition ability under different pH, reaction times, and metal ion conditions, as well as the Limit of Detection of the probe. Our findings indicate that this probe is a highly stable tool for detecting chiral lysine.

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Highly sensitive and selective colorimetric sensor for thiocyanate based on electrochemical oxidation-assisted complexation reaction with Gold nanostars etching

Cui

Wei

Hao

et al. 2020

Journal of Hazardous Materials

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Study of the Zn^IIComplexes of 1,1′‐Binaphthyl‐Based Schiff Bases: Fluorescent Detection of Thiocyanate

Cited by 7 publications

References 24 publications

Enantioselective Dynamic Exchange Reactions of Imines

Enantioselective Dynamic Exchange Reactions of Imines

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

Highly sensitive and selective colorimetric sensor for thiocyanate based on electrochemical oxidation-assisted complexation reaction with Gold nanostars etching

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Study of the ZnIIComplexes of 1,1′‐Binaphthyl‐Based Schiff Bases: Fluorescent Detection of Thiocyanate

Cited by 7 publications

References 24 publications

Enantioselective Dynamic Exchange Reactions of Imines

Enantioselective Dynamic Exchange Reactions of Imines

Spectroscopic Study of a Novel Binaphthyl Amine Fluorescent Probe for Chiral Recognition of DL-Lysine

Highly sensitive and selective colorimetric sensor for thiocyanate based on electrochemical oxidation-assisted complexation reaction with Gold nanostars etching

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Study of the Zn^IIComplexes of 1,1′‐Binaphthyl‐Based Schiff Bases: Fluorescent Detection of Thiocyanate