Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg（Ⅱ） Ion and Its Application in Adsorption

doi:10.19894/j.issn.1000-0518.210107

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (5): 760-768.DOI: 10.19894/j.issn.1000-0518.210107

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Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg（Ⅱ） Ion and Its Application in Adsorption

Song-Song XUE¹, Zheng-Feng XIE¹^,²(), Jia-Wei HE¹, Tian-Yi ZHANG¹, Bao-Ping XIA¹, Yu-Qin LI¹

^1.Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province，College of Chemistry and Chemical Engineering，Southwest Petroleum University，Chengdu 610500，China
^2.Research Institute of Industrial Hazardous Waste Disposal and Resource Utilization，Southwest Petroleum University，Chengdu 610500，China

Received:2021-03-10 Accepted:2021-06-26 Published:2022-05-01 Online:2022-05-24
Contact: Zheng-Feng XIE
About author:xiezhf@swpu.edu.cn
Supported by:
Sichuan Youth Science and Technology Innovation Research Team Project(2020JDTD0018)

1. Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg(II).pdf(288KB)

Abstract

Abstract:

A simple fluorescent probe （Z）-N'-（pyrene-1-ylmethylene） benzenesulfonylhydrazone （BSB） was designed and synthesized by using benzenesulfonylhydrazine and 1-pyrene-formaldehyde as materials， and its structure was characterized by hydrogen nuclear magnetic resonance spectroscopy （¹H NMR）. BSB shows high selectivity， specificity and rapid response to Hg²⁺. The detection limit is 2.07×10^-7 mol/L， and the response time is only 15 s. The optimal response mechanism is explored through job's curve， ¹H NMR titration experiment and high resolution mass spectrometry （HRMS）. BSB could detect Hg²⁺ in different water samples. Interestingly， a novel polymer material （PAM?BSB） with high Hg²⁺ removal performance is prepared by doping BSB with polyacrylamide （PAM）. The removal rate is 99.63%， and the micro-morphology of PAM-BSB before and after adsorption is observed by scanning electron microscopy （SEM）.

Key words: Fluorescent probe, Mercury ions, Doping, Adsorption

CLC Number:

O621

Song-Song XUE, Zheng-Feng XIE, Jia-Wei HE, Tian-Yi ZHANG, Bao-Ping XIA, Yu-Qin LI. Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg（Ⅱ） Ion and Its Application in Adsorption[J]. Chinese Journal of Applied Chemistry, 2022, 39(5): 760-768.

Figures/Tables 11

Fig.1 （A） Various cations （1.0×10-4 mol/L） are added to BSB （1.0×10-5 mol/L） DMSO/H2O （volume ratio 1∶1，pH=7） and （B） fluorescence emission spectra （excitation wavelength 387 nm， slit width 5 nm × 5 nm）

Fig.2 Competitive diagram of Hg2+ （1.0×10-4 mol/L） in the presence of various cations （1.0×10-4 mol/L） in DMSO/H2O （V∶V = 1∶1，pH = 7） solution of BSB （excitation wavelength 387 nm， slit width 5 nm × 5 nm）

Fig.3 （A） Fluorescence spectra of BSB （1×10-5 mol/L） in DMSO/H2O （volume ratio1∶1，pH=7） for Hg2+ of different concentrations and （b） fluorescence dot graphs of BSB （1×10-5 mol/L） for Hg2+ of different concentrations

Fig.4 Time response of BSB （1.0×10-5 mol/L） to Hg2+ （1.0×10-4 mol/L） in DMSO/H2O （volume ratio 1∶1，pH=7）solution （excitation wavelength 387 nm， slit width 5 nm × 5 nm）

Fig.5 1H NMR titration with BSB （1×10-5 mol/L） and different concentrations of Hg2+

Fig.6 Possible binding mechanism of BSBand Hg2+

Table 1 Determination of Hg2+ in different water samples

样品 Sample	加入 Added/（mol·L^-1）	测定 Found/（mol·L^-1）	回收率 Recovery/%
自来水 Tape water	1.0×10^-6	0.97×10^-6	97
	5.0×10^-6	5.13×10^-6	102.6
	1.0×10^-5	1.12×10^-5	112
	5.0×10^-5	4.89×10^-5	97.8
矿泉水 Mineral water	1.0×10^-6	1.02×10^-6	102
	5.0×10^-6	5.17×10^-6	103.4
	1.0×10^-5	0.98×10^-5	98
	5.0×10^-5	4.82×10^-5	96.4
河水 River water	1.0×10^-6	1.26×10^-6	126
	5.0×10^-6	5.62×10^-6	112.4
	1.0×10^-5	0.93×10^-5	93
	5.0×10^-5	5.21×10^-5	104.2

Fig.7 （A） and （B） are the pictures of PAM?BSB under natural light and ultraviolet light before adsorption respectively；（C） and （D） are the pictures of PAM-BSB under natural light and ultraviolet light after adsorption， respectively

Fig.8 The adsorption performance of PAM and PAM?BSB on different metal ions （0.1 mol/L）（Mixed： shows the adsorption performance of PAM and PAM-BSB on mercury ions when other ions coexist）

Fig.9 （A） SEM and （B） EDS micrographs before PAM?BSB adsorption of Hg2+；（C） SEM and （D） EDS micrographs after PAM-BSB adsorption of Hg2+

References 32

1	CARTER K P， YOUNG A M， PALMER A E. Fluorescent sensors for measuring metal ions in living systems［J］. Chem Rev， 2014， 114（8）： 4564-4601.
2	PARAMANIK B， BAIN D， PATRA A. Making and breaking of DNA-metal base pairs： Hg²⁺ and Au nanocluster based off/on probe［J］. Indian J Chem A， 2016， 120（30）： 17127-17135.
3	MAHATO P， SAHA S， SURESH E， et al. Ratiometric detection of Cr³⁺ and Hg²⁺ by a naphthalimide-rhodamine based fluorescent probe［J］. Inorg Chem， 2012， 51： 1769-1777.
4	ZHAO Y， LI Y， LONG Y， et al. Highly selective fluorescence turn-on determination of fluoride ions via chromogenic aggregation of a silyloxy-functionalized salicylaldehyde azine［J］. Tetrahedron Lett， 2017， 58（13）： 1351-1355.
5	WANG Y， LIN L， LIU J， et al. Ferric ion induced enhancement of ultraviolet vapour generation coupled with atomic fluorescence spectrometry for the determination of ultratrace inorganic arsenic in surface water［J］. The Analyst， 2016， 141（4）： 1530-1536.
6	YANG L， SU Y， GENG Y， et al. A red-emitting fluorescent probe for the detection of Hg²⁺ in aqueous medium， living cells and organisms with a large Stokes shift［J］. Org Biomol Chem， 2018， 16（27）： 5036-5042.
7	胡明明，樊江莉，李宏林，等．荧光探针可视化检测水溶液中铜离子［J］．分析化学， 2011， 39（8）： 1195-1200．
	HU M M， FAN J L， LI H L， et al.A sensitive probe for determination of Cu²⁺ with optical detection in aqueous solution［J］. Chinese J Anal Chem， 2011， 39（8）： 1195-1200．
8	戚少龙，杜建时，李容杭，等. 水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测［J］. 分析化学， 2020， 48（3）： 347-354.
	QI S L， DU J S， LI R H， et al. Synthesis of water-soluble fluorescent probe for dual detection of HSO₃ and pH value［J］. Chinese J Anal Chem， 2020， 48（3）： 347-354.
9	XU J， WANG Z， LIU C， et al. A highly selective colorimetric and long-wavelength fluorescent probe for the detection of Hg²⁺［J］. Luminescence， 2018， 33（6）： 1122-1127.
10	李迪，孙建强，许丙嵩，等. 基于查尔酮衍生物的铜离子探针的设计合成［J］. 应用化学， 2020， 37（11）： 1268-1275.
	LI D， SUN J Q， XU B S， et al. Design and synthesis of chalcone－based derivative for sensing Cu²⁺ ion［J］. Chinese J Appl Chem， 2020， 37（11）： 1268-1275.
11	陈丽娟，刘仁勇，赵丹，等. 聚乙烯亚胺修饰的碳点荧光探针用于检测汞离子［J］. 分析化学， 2020， 48（8）： 1067-1074.
	CHEN L J， LIU R Y， ZHAO D， et al. A novel fluorescent probe for mercury ion detection based on polyethyleneimine modified carbon dots ［J］. Chinese J Anal Chem， 2020， 48（8）： 1067-1074.
12	HUO F J， ZHANG Y Q， KANG J， et al. A novel alkyne compound as a Pd（Ⅱ） fluorescent probe in aqueous medium and its bioimaging［J］. Sens Actuators B： Chem， 2017， 243： 429-434.
13	ZHANG H F， YIN C X， LIU T， et al. Selective “off-on” detection of magnesium （Ⅱ） ions using a naphthalimide-derived fluorescent probe［J］. Dyes Pigm， 2017， 146： 344-351.
14	ZHU Z F， DING H C， WANG Y S， et al. A ratiometric and colorimetric fluorescent probe for the detection of mercury ion based on rhodamine and quinoline‑benzothiazole conjugated dyad［J］. J Photochem Photobiol A， 2020， 400： 112657-112666.
15	REENA V R， SMRITILEKHA B， PRASENJIT M， et al. Mechanochemical synthesis of a fluorescein-based sensor for the selective detection and removal of Hg²⁺ ions in industrial effluents［J］. ACS Omega， 2020， 5（10）： 4982-4990.
16	PAVEL A P， YURI V F， OLGA A F. Selective fluorometric sensing of Hg²⁺ in aqueous solution by the inhibition of PET from dithia-15-crown-5 ether receptor conjugated to 4-amino-1，8-naphthalimide fluorophore［J］. J Photochem Photobiol A， 2018，364： 124-129.
17	ZHANG H F， LIU T， YIN C X， et al. A novel ratiometric fluorescent probe based on 1，8-naphthalimide for the detection of Ho³⁺and its bioimaging［J］. Spectrochim Acta A， 2017， 174： 230-235.
18	ZHANG H F， YIN C X， LIU T， et al. “Turn-on” fluorescent probe detection of Ca²⁺ ions and applications to bioimaging［J］. Spectrochim Acta A， 2017， 180： 211-216.
19	PANG X， GAO L， FENG H， et al. A peptide-based multifunctional fluorescent probe for Cu²⁺， Hg²⁺ and biothiols［J］. New J Chem， 2018， 42（12）： 15770-15777.
20	CUI T， YU S， CHEN Z， et al. Rational design of fluorescent probe for Hg²⁺ by changing the chemical bond type［J］. RSC Adv， 2018， 8： 12276-12281.
21	HUANG X， LU Z， WANG Z， et al. A colorimetric and turn-on fluorescent chemosensor for selectively sensing Hg²⁺ and its resultant complex for fast detection of I^- over S^2-［J］. Dyes Pigm， 2016， 128： 33-40.
22	GE Y， XING X， LIU A， et al. A novel imidazo［1，5-a］pyridine-rhodamine FRET system as an efficient ratiometric fluorescent probe for Hg²⁺ in living cells［J］. Dyes Pigm， 2017， 146： 136-142.
23	ZHANG L， SHI Y， SHENG Z， et al. Bioluminescence imaging of selenocysteine in vivo with a highly sensitive probe［J］. ACS Sens， 2019， 4（12）： 1234-1242.
24	MIN K S， MANIVANNAN R， SON Y A. Rhodamine-fluorene based dual channel probe for the detection of Hg²⁺ ions and its application in digital printing［J］. Sens Actuators B： Chem， 2018， 261： 545-552.
25	ZHANG Y， LENG J. Theoretical studies on two-photon fluorescent Hg²⁺ probes based on the coumarin-rhodamine system［J］. Sensors-Basel， 2017， 17（7）： 346-258.
26	JESUS S， IXONE E， BINGEN G M， et al. Phase-selective staining of model and cell membranes， lipid droplets and lipoproteins with ﬂuorescent solvatochromic pyrene probes［J］. BBA-Biomembranes， 2021， 1863（1）： 183470-183479.
27	YUE Y Y， XIE Z F， CHU Y C， et al. A novel fluorescent probe based on spiro［chromeno［2，3-c］pyrazole-4，1-［2］benzofuran］-3-one for detecting copper（Ⅱ） ions in aqueous solution［J］. Russ J Org Chem， 2019， 55（6）： 866-873.
28	CHU Y C， XIE Z F， YUE Y Y， et al. New fast， highly selective probe with both aggregation-induced emission enhancement and intramolecular charge-transfer characteristics for homocysteine detection［J］. ACS Omega， 2019， 4（3）： 5367-5373.
29	REN X D， XIE Z F， WU H， et al. Multiple-responsive organogels with self-colorimetric chemo sensing responsiveness towards Hg²⁺ ions［J］. Colloid Surf A， 2019， 583： 124003-124008.
30	薛松松，解正峰，褚义成，等. 高选择性快速检测Hg²⁺的磺酰腙型探针的合成及在吸附和HeLa细胞中的应用［J］. 有机化学， 2021， 41（3）： 1138-1145.
	XUE S S， XIE Z F， CHU Y C， et al. Synthesis of sulfonylhydrazone type probe with high selectivity for rapid detection of mercury and its application in adsorption and HeLa cells［J］. Chinese J Org Chem， 2021， 41（3）： 1138-1145.
31	XIE Z F， KONG X J， FENG L， et al. A novel highly selective probe with both aggregation-induced emission enhancement and intramolecular charge transfer characteristics for CN^- detection［J］. Sens Actuators B： Chem， 2018， 257： 154-165.
32	LI Y Q， SHI W， MA J C， et al. A novel optical probe for Hg²⁺ in aqueous media based on mono-thiosemicarbazone Schiff base［J］. Spectrochim Acta A， 2017， 338： 1-7.

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Synthesis of Sulfonylhydrazone Probe with High Selectivity and Rapid Identification of Hg（Ⅱ） Ion and Its Application in Adsorption

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