Synthesis and Spectroscopic Investigation of a Novel Sensitive and Selective Fluorescent Chemosensor for Ag Based on a BINOL-glucose Derivative

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 11

PMID 35540164

Authors

Yu Hu

Huayin Shen

Xiaohan Zhang

Yang Liu

Xiaoxia Sun

Affiliations

Soon will be listed here.

Abstract

Based on a versatile 2,2'-binaphthol (BINOL) backbone, a novel BINOL-glucose derivative fluorescent sensor was synthesized using a click reaction. The fluorescence responses of the BINOL-glucose derivative (,β-d)-1 conclude that it can be used as a specific fluorescent chemical sensor for Ag in the presence of a large number of competing metal ions without any obvious interference from other metal ions. Mass spectrometric and NMR spectroscopic data were used to study the mechanism, and implied the formation of a 1 + 1 complex between BINOL-glucose 1 and Ag. Both the oxygen atoms of -BINOL and two nitrogen atoms of triazole were involved in coordinating the silver ion.

Citing Articles

Self-Assembled Nanotubes Based on Chiral H-BINOL Modified with 1,2,3-Triazole to Recognize Bi Efficiently by ICT Mechanism.

Tao J, Guo F, Sun Y, Sun X, Hu Y Micromachines (Basel). 2024; 15(1).

PMID: 38276862 PMC: 10821062. DOI: 10.3390/mi15010163.

Preparation of novel 1,2,3-triazole furocoumarin derivatives click chemistry and their anti-vitiligo activity.

Niu C, Lu X, Aisa H RSC Adv. 2022; 9(3):1671-1678.

PMID: 35518056 PMC: 9059643. DOI: 10.1039/c8ra09755k.

A Sensitive Near-Infrared Fluorescent Probe for Detecting Heavy Metal Ag⁺ in Water Samples.

Zhang Y, Ye A, Yao Y, Yao C Sensors (Basel). 2019; 19(2).

PMID: 30634622 PMC: 6358871. DOI: 10.3390/s19020247.

References

Lau Y, Rutledge P, Watkinson M, Todd M . Chemical sensors that incorporate click-derived triazoles. Chem Soc Rev. 2011; 40(5):2848-66. DOI: 10.1039/c0cs00143k. View

Pu L . 1,1'-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials. Chem Rev. 2002; 98(7):2405-2494. DOI: 10.1021/cr970463w. View

Nolan E, Lippard S . A "turn-on" fluorescent sensor for the selective detection of mercuric ion in aqueous media. J Am Chem Soc. 2003; 125(47):14270-1. DOI: 10.1021/ja037995g. View

Xu M, Lin J, Hu Q, Pu L . Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching. J Am Chem Soc. 2002; 124(47):14239-46. DOI: 10.1021/ja020989k. View

Xie J, Menand M, Maisonneuve S, Metivier R . Synthesis of bispyrenyl sugar-aza-crown ethers as new fluorescent molecular sensors for Cu(II). J Org Chem. 2007; 72(16):5980-5. DOI: 10.1021/jo070315y. View

Pu L . Simultaneous Determination of Concentration and Enantiomeric Composition in Fluorescent Sensing. Acc Chem Res. 2017; 50(4):1032-1040. DOI: 10.1021/acs.accounts.7b00036. View

Pu L . Enantioselective fluorescent sensors: a tale of BINOL. Acc Chem Res. 2011; 45(2):150-63. DOI: 10.1021/ar200048d. View

Song Z, He X, Li C, Gao L, Wang Z, Tang Y . Preparation of triazole-linked glycosylated α-ketocarboxylic acid derivatives as new PTP1B inhibitors. Carbohydr Res. 2010; 346(1):140-5. DOI: 10.1016/j.carres.2010.10.023. View

Wang C, Zeng C, Zhang X, Pu L . Enantioselective Fluorescent Recognition of Amino Acids by Amide Formation: An Unusual Concentration Effect. J Org Chem. 2017; 82(23):12669-12673. DOI: 10.1021/acs.joc.7b02456. View

10.

Tornoe C, Christensen C, Meldal M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9):3057-64. DOI: 10.1021/jo011148j. View

11.

Li Z, Lin J, Pu L . A cyclohexyl-1,2-diamine-derived bis(binaphthyl) macrocycle: enhanced sensitivity and enantioselectivity in the fluorescent recognition of mandelic acid. Angew Chem Int Ed Engl. 2005; 44(11):1690-3. DOI: 10.1002/anie.200462471. View

12.

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

13.

Wan A, Conyers R, Coombs C, MASTERTON J . Determination of silver in blood, urine, and tissues of volunteers and burn patients. Clin Chem. 1991; 37(10 Pt 1):1683-7. View

14.

Lin J, Hu Q, Xu M, Pu L . A practical enantioselective fluorescent sensor for mandelic acid. J Am Chem Soc. 2002; 124(10):2088-9. DOI: 10.1021/ja011971x. View

15.

Yu S, Pu L . Pseudoenantiomeric fluorescent sensors in a chiral assay. J Am Chem Soc. 2010; 132(50):17698-700. DOI: 10.1021/ja1086408. View

16.

Yuan M, Zhou W, Liu X, Zhu M, Li J, Yin X . A multianalyte chemosensor on a single molecule: promising structure for an integrated logic gate. J Org Chem. 2008; 73(13):5008-14. DOI: 10.1021/jo8005683. View

17.

Liu H, Hou X, Pu L . Enantioselective precipitation and solid-state fluorescence enhancement in the recognition of alpha-hydroxycarboxylic acids. Angew Chem Int Ed Engl. 2008; 48(2):382-5. DOI: 10.1002/anie.200804538. View

18.

Song T, Cao Y, Zhao G, Pu L . Fluorescent Recognition of Zn by Two Diastereomeric Salicylaldimines: Dramatically Different Responses and Spectroscopic Investigation. Inorg Chem. 2017; 56(8):4395-4399. DOI: 10.1021/acs.inorgchem.6b03062. View

19.

Zhu M, Zhou Y, Yang L, Li L, Qi D, Bai M . Synergistic coupling of fluorescent "turn-off" with spectral overlap modulated FRET for ratiometric Ag+ sensor. Inorg Chem. 2014; 53(22):12186-90. DOI: 10.1021/ic502141q. View

20.

Chen X, Huang Z, Chen S, Li K, Yu X, Pu L . Enantioselective gel collapsing: a new means of visual chiral sensing. J Am Chem Soc. 2010; 132(21):7297-9. DOI: 10.1021/ja102480t. View