Hui-zhen WANG, Song-song XUE, Xia ZHOU, et al. Synthesis of Highly Selective Copper Ion Probe and Its Application in Adsorption. [J]. Chinese Journal of Luminescence 42(9):1427-1435(2021)
DOI:
Hui-zhen WANG, Song-song XUE, Xia ZHOU, et al. Synthesis of Highly Selective Copper Ion Probe and Its Application in Adsorption. [J]. Chinese Journal of Luminescence 42(9):1427-1435(2021) DOI: 10.37188/CJL.20210134.
Synthesis of Highly Selective Copper Ion Probe and Its Application in Adsorption增强出版
A novel Schiff base fluorescent probe (N'-(4-(diphenylamino)benzylidene)-3-hydroxy-2-Naphtho-hydrazide)(L) was designed and synthesized using 3-hydroxy-2-naphthoic acid hydrazide and 4-diphenylaminobenzaldehyde as raw materials. The structure of L was characterized through
1
H NMR
13
C NMR
HR-MS
IR and X-ray. The study found that probe L showed high sensitivity and selectivity response to copper ions(Cu
2+
) in H
2
O/DMSO(
V
∶
V
=3∶7
pH=7) solution. The possible mechanism of coordination between L and Cu
2+
was studied by HR-MS
1
H NMR and DFT calculation. PAML was prepared by the method of doping L into polyacrylamide(PAM). PAML had high adsorption of Cu
2+
and the removal rate of Cu
2+
by PAML in water reached 96.99%
in addition
the color change could be distinguished by naked eyes under UV lamp. The microscopic morphology of PAML before and after adsorption of Cu
YAN F Y, SUN X D, ZHANG R Q, et al. Enhanced fluorescence probes based on Schiff base for recognizing Cu2+ and effect of different substituents on spectra [J].Spectrochim. Acta Part A: Mol. Biomol. Spectrosc., 2019, 222:117222.
THANGARAJ A, BHARDWAJ V, SAHOO S K. A multi-analyte selective dansyl derivative for the fluorescence detection of Cu(ii) and cysteine [J].Photochem. Photobiol. Sci., 2019, 18(6):1533-1539.
DENG J, ZHOU Y, PAN X T, et al. Synthesis and properties of a new turn-on Zn2+ fluorescence probe [J].J. Hubei Norm. Univ. (Nat. Sci.), 2021, 41(2):34-37. (in Chinese)
WAN X J, KE H Q, TANG J N, et al. Acid environment-improved fluorescence sensing performance:a quinoline Schiff base-containing sensor for Cd2+ with high sensitivity and selectivity [J].Talanta, 2019, 199:8-13.
TEKURI V, SAHOO S K, TRIVEDI D R. Hg2+ induced hydrolysis of thiazole amine based Schiff base:colorimetric and fluorogenic chemodosimeter for Hg2+ ions in an aqueous medium [J].Spectrochim. Acta Part A:Mol. Biomol. Spectrosc., 2019, 218:19-26.
HALDER S, HAZRA A, ROY P. Colorimetric and fluorescence sensing of pH with a Schiff-base molecule [J].J. Lumin., 2018, 195:326-333.
XIE J L, PENG H N, HU X, et al. A fluorescence probe for Ni2+ based on isonicotinoyl and 2-hydroxy-1-naphthaldehyde hydrazone [J].Chin. J. Anal. Lab., 2018, 37(8):954-958. (in Chinese)
XIAO N, ZHANG C. Selective monitoring of Cu(Ⅱ) with a fluorescence-on naphthalene-based probe in aqueous solution [J].Inorg. Chem. Commun., 2019, 107:107467.
WU H M, GUO Y, CAO J F, et al. Synthesis and spectral properties of zinc ion-enhanced fluorescence probe based on naphthoyl acylhydrazone [J].Chin. J. Lumin., 2018, 39(5):621-626. (in Chinese)
WANG Z G, WANG Y, DING X J, et al. A highly selective colorimetric and fluorescent probe for quantitative detection of Cu2+/Co2+:the unique ON-OFF-ON fluorimetric detection strategy and applications in living cells/zebrafish [J].Spectrochim. Acta Part A:Mol. Biomol. Spectrosc., 2020, 228:117763.
SUN X J, LIU T T, Li N N, et al. A novel dual-function probe for recognition of Zn2+ and Al3+ and its application in real samples [J].Spectrochim. Acta Part A:Mol. Biomol. Spectrosc., 2020, 228:117786.
SAHOO P R, KUMAR A, KUMAR A, et al. Synthesis and optical properties of copper(Ⅱ) and nickel(Ⅱ) complexes of a highly fluorescent morpholine-derivative [J].Polyhedron., 2019, 171:559-570.
PARK G J, LEE M M, YOU G R, et al. A turn-on and reversible fluorescence sensor with high affinity to Zn2+ in aqueous solution [J].Tetrahedron. Lett., 2014, 55(15):2517-2522.
LIU Z Z, XU H J, SHENG L Q, et al. A highly selective colorimetric and fluorescent chemosensor for Al(Ⅲ) based-on simple naphthol in aqueous solution [J].Spectrochim. Acta Part A:Mol. Biomol. Spectrosc., 2016, 157:6-10.
LEE S, JUNG K Y, PARK J, et al. Synthesis of potent chemical inhibitors of dynamin GTPase [J].Bioorg. Med. Chem. Lett., 2010, 20(16):4858-4864.
SHAO Y Y, YAN T, WANG K, et al. Soil heavy metal lead pollution and its stabilization remediation technology [J].Energy Rep., 2020, 6 Suppl 8:122-127.
CHEN S H, CHEN Q, LUO S H, et al. Progress in design, synthesis and application of triphenylamine-based fluorescent probes [J].Chin. J. Org. Chem., 2021, 41(3):919-933. (in Chinese)
QIN G W, NIU Z D, YU J D, et al. Soil heavy metal pollution and food safety in China:effects, sources and removing technology [J].Chemosphere., 2021, 267:129205.
YE F, LIANG X M, WU N, et al. A new perylene-based fluorescent pH chemosensor for strongly acidic condition [J].Spectrochim. Acta Part A:Mol. Biomol. Spectrosc., 2019, 216:359-364.
WANG B, YU C. Aptamer induced assembly of fluorescent nitrogen-doped carbon dots on gold nanoparticles for sensitive detection of AFB1 [J].Angew. Chem., 2010, 49(8):1485-1488.
LI J F, WU Y Z, SONG F Y, et al. A highly selective and sensitive polymer-based OFF-ON fluorescent sensor for Hg2+ detection incorporating salen and perylenyl moieties [J].J. Mater. Chem., 2012, 22(2):478-482.
LANGHALS H, HOFER A. Chromophores arranged as “magnetic meta atoms”:building blocks for molecular metamaterials [J].J. Org. Chem., 2013, 78(12):5889-5897.
GÖRL D, ZHANG X, WÜRTHNER F. Molecular assemblies of perylene bisimide dyes in water [J].Angew. Chem. Int. Ed., 2012, 51(26):6328-6348.
FENG X L, AN Y X, YAO Z Y, et al. A turn-on fluorescent sensor for pyrophosphate based on the disassembly of Cu2+-mediated perylene diimide aggregates [J].ACS Appl. Mater. Interfaces., 2012, 4(2):614-618.
D'AMBROSIO D, REICHENBACH P, MICHELI E, et al. Specific binding of telomeric G-quadruplexes by hydrosoluble perylene derivatives inhibits repeat addition processivity of human telomerase [J].Biochimie., 2012, 94(3):854-863.
YANG X, LIU L H, TAN W F, et al. Remediation of heavy metal contaminated soils by organic acid extraction and electrochemical adsorption [J].Environ. Pollut., 2020, 264:114745.
PENG W J, LI H Q, LIU Y Y, et al. A review on heavy metal ions adsorption from water by graphene oxide and its composites [J].J. Mol. Liq., 2017, 230:496-504.
KOBYA M, DEMIRBAS E, SENTURK E, et al. Adsorption of heavy metal ions from aqueous solutions by activated carbon prepared from apricot stone [J].Bioresour. Technol., 2005, 96(13):1518-1521.
CHEN J H, XING H T, SUN X, et al. Highly effective removal of Cu(Ⅱ) by triethylenetetramine-magnetic reduced graphene oxide composite [J].Appl. Surf. Sci., 2015, 356:355-363.
ZHANG C L, SUN Y D, WANG J, et al. Synthesis and application of quinolinone derivative fluorescent probe for high selective detection of Hg2+ [J].Chem. J. Chin. Univ., 2020, 41(8):1785-1791. (in Chinese)
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