Preparation of magnetic metal-organic frameworks-polydopamine for extraction and detection of cationic dyes from water samples in a fishery

doi:10.3724/SP.J.1123.2019.05045

Abstract

Abstract:

The catechol group of dopamine (DA) can chelate with the metal ion in the crystal of molecular organic frameworks (MOFs). Based on this principle, a magnetic metal polydopamine (PDA) framework (Fe₃O₄@Z67D) was prepared using ZIF-67 as the template, which was etched by DA, followed by polymerization of the DA monomers to form a PDA coating with a porous structure. The morphology, structure, and properties of the material were determined by various characterization methods. Fe₃O₄@Z67D was used as an adsorbent, and a magnetic solid-phase extraction/high-performance liquid chromatography method for the determination of two cationic dyes, methylene blue (MB) and crystal violet (CV), was established. Under the optimized extraction and detection conditions, the linear ranges for MB and CV were 0.5-200 μg/L and 0.01-50 μg/L, respectively, and the corresponding detection limits were 0.04 μg/L and 0.008 μg/L. The experimental results showed that the enrichment factors of Fe₃O₄@Z67D for the two dyes were 777 and 688, respectively. The extraction performance was largely unaffected even after the new material was reused 10 times. The method was applied successfully for the adsorption and detection of the above mentioned two dyes in fishpond water. The spiking recoveries of the two cationic dyes ranged from 82.0% to 109.0%, and the RSD was lower than 2.9%.

Key words: metal-organic frameworks (MOFs), polydopamine, magnetic solid-phase extraction (MSPE), high-performance liquid chromatography (HPLC), cationic dyes

YANG Xiaohan, WU Wenqian, WANG Bin, LIN Feng, WU Xiaohai, LU Xin. Preparation of magnetic metal-organic frameworks-polydopamine for extraction and detection of cationic dyes from water samples in a fishery[J]. Chinese Journal of Chromatography, 2020, 38(2): 195-205.

Figures/Tables 13

Fig. 1 Schemes of (a) synthesis of Fe3O4@Z67D and (b) MSPE process PEG: polyethylene glycol; EG: ethylene glycol; PDA: polydopamine; MSPE: magnetic solid-phase extraction.

Fig. 2 (a) X-ray diffraction spectra and (b) infrared spectra of Fe3O4, ZIF-67, Fe3O4@ZIF-67 and Fe3O4@Z67D

Fig. 3 Scanning electron microscope images of (a) Fe3O4, (b) Fe3O4@ZIF-67, (c) Fe3O4@Z67D and transmission electron microscopy images of (d) Fe3O4@ZIF-67 and (e, f) Fe3O4@Z67D

Fig. 4 Energy dispersive X-ray spectra of (a) Fe3O4@ZIF-67 and (b) Fe3O4@Z67D

Fig. 5 X-ray photoelectron spectroscopy full-scan analysis of (a) Fe3O4@Z67D and high resolution X-ray photoelectron spectroscopy analysis of (b) Fe 2p, (c) Co 2p, (d) O 1s, (e)C 1s and (f) N 1s

Fig. 6 (a)N2 adsorption-desorption isotherm and (b) pore size distribution of Fe3O4@ZIF-67 and Fe3O4@Z67D

Fig. 7 Hysteresis loops of Fe3O4, Fe3O4@ZIF-67 and Fe3O4@Z67D

Fig. 8 Effects of (a) the amount of Fe3O4@Z67D, (b) the extraction time, (c) the volume and (d) pH of sample solution, and (e) the type and (e) volume of the eluent solvents on the recoveries of the two dyes (n=3) MeOH: methanol; ACN: acetonitrile; HAc: acetic acid.

Fig. 9 Recoveries obtained on Fe3O4@Z67D after reuse(n=3)

Table 1 Analytical performance data of the MSPE-HPLC method for the determination of the two dyes

Analyte	Regression equation	Linear range/(μg/L)	R²	LOD/(μg/L)	RSD/%(n=5)	Enrichment factor
Y: peak area; X: mass concentrition, μg/L.
MB	Y=6.0×10⁴X-2.8×10⁴	0.5-200	0.9999	0.04	1.2	777
CV	Y=1.0×10⁵X+6.2×10³	0.01-50	0.9998	0.008	3.6	688

Table 2 Analytical results of MB and CV in fishpond water samples and the spiked recoveries (n=5)

Analyte	Added/(μg/L)	Found/(μg/L)	Recovery/%	RSD/%
-: not applicable.
MB	0	0.7	--
	1	0.9	88.6	2.3
	10	9.0	90.3	2.9
CV	0	0.2	--
	5	5.5	109.0	2.2
	50	41.0	82.0	1.4

Fig. 10 Chromatograms obtained from fishpond water samples treated after MSPE a. blank sample; b. sample spiked with 10 μg/L MB and 5 μg/L CV.Conditions: SpursilTM C18 column(250 mm×4.6 mm, 5 μm); mobile phase, methanol-0.0125 mol/L ammonium acetate buffer solution (85:15, v/v)(pH adjusted to 4.5 by acetic acid); flow rate, 1.0 mL/min; detection wavelength, 580 nm; injection volume, 20 μL; column temperature, 35 ℃.

Table 3 Comparison of this method with reported methods

Method	Matrix	Linear range/(μg/L)		LOD/(μg/L)		Recovery/%	RSD/%	Reference
Method	Matrix	MB	CV	MB	CV	Recovery/%	RSD/%	Reference
PLS-1: partial least squares method; NACE: non-aqueous capillary electrophoresis; ED: electrochemical detection; -: not available; *: μg/kg.
SPE-UPLC-MS-MS	silver carp	5.0-200	2.5-100	0.30^*	0.15^*	75.4-87.8	4.33-10.4	[53]
SPE-UV/PLS-1	stream water	150-8000	120-8000	48	28	79.8-83.6	2.3-4.2	[54]
SPE-NACE-ED	river and lake water	100-700	100-700	0.13	0.11	43-98	-	[55]
MSPE-HPLC-UV	fishpond water	0.5-200	0.01-50	0.04	0.008	82.0-109.0	1.4-2.9	this work

References

1	Moawed E A , El-Hagrasy M A , Senan A E A . Int J Environ Sci Te, 2019 16
2	Zhao J , Wei D Q , Yang Y L . J Sep Sci, 2016, 39 (12): 2347
3	Sarma G K , Sen Gupta S S , Bhattacharyya K G . J Environ Manage, 2016, 171: 1
4	?afaík I , ?afa íková M . Water Res, 2002, 36 (1): 196
5	Dowling G , Mulder P P , Duffy C , et al. Anal Chim Acta, 2007, 586 (1/2): 411
6	Andersen W C , Turnipseed S B , Karbiwnyk C M , et al. Anal Chim Acta, 2009, 637 (1/2): 279
7	Hameed B H , Ahmad A L , Latiff K N A . Dyes Pigments, 2007, 75 (1): 143
8	?afaíková M , ?afaík I . J Magn Magn Mater, 1999, 194 (1/2/3): 108
9	Herrero-Latorre C , Barciela-Garcia J , Garcia-Martin S , et al. Anal Chim Acta, 2015, 892: 10
10	Han Q , Wang Z H , Xia J F , et al. Talanta, 2012, 101: 388
11	Wierucka M , Biziuk M . TrAC-Trends Anal Chem, 2014, 59: 50
12	Maddah B , Shamsi J . J Chromatogr A, 2012, 1256: 40
13	Gao Q , Zheng H B , Luo D , et al. Anal Chim Acta, 2012, 720: 57
14	Liu Q J , Sun N R , Deng C H . TrAC-Trends Anal Chem, 2019, 110: 66
15	Zhou J W , Wang B . Chem Soc Rev, 2017, 46 (22): 6927
16	Furukawa H , Cordova K E , O'Keeffe M , et al. Science, 2013, 341 (6149): 1230444
17	Zhu Q L , Xu Q . Chem Soc Rev, 2014, 43 (16): 5468
18	Sohrabi M R , Matbouie Z , Asgharinezhad A A , et al. Microchim Acta, 2013, 180 (7/8): 589
19	Barreto A S , Da Silva R L , Dos Santos Silva S C G , et al. J Sep Sci, 2010, 33 (23/24): 3811
20	Hao L , Liu X L , Wang J T , et al. Talanta, 2015, 142: 104
21	Lirio S , Liu W L , Lin C L , et al. J Chromatogr A, 2016, 1428: 236
22	Rocio-Bautista P , Pino V , Ayala J H , et al. J Chromatogr A, 2016, 1436: 42
23	Rocio-Bautista P , Pino V , Pasan J , et al. Talanta, 2018, 179: 775
24	Yang X Q , Yang C X , Yan X P . J Chromatogr A, 2013, 1304: 28
25	Zhang S L , Du Z , Li G K . Talanta, 2013, 115: 32
26	Maya F , Cabello C P , Frizzarin R M , et al. TrAC-Trends Anal Chem, 2017, 90: 142
27	Chen X F , Ding N , Zang H , et al. J Chromatogr A, 2013, 1304: 241
28	Patil N , Jerome C , Detrembleur C . Prog Polym Sci, 2018, 82: 34
29	Rahim M A , Kristufek S L , Pan S , et al. Angew Chem Int Ed Engl, 2019, 58 (7): 1904
30	Hofman A H , van Hees I A , Yang J , et al. Adv Mater, 2018, 30 (19): e1704640
31	Long Y K , Xiao L , Cao Q H , et al. Chem Commun, 2017, 53 (78): 10831
32	Hu M , Ju Y , Liang K , et al. Adv Funct Mater, 2016, 26 (32): 5827
33	Wang H , Zhu W , Ping Y , et al. ACS Appl Mater Interfaces, 2017, 9 (16): 14258
34	Zhu W , Xiang G L , Shang J , et al. Adv Funct Mater, 2018, 28 (16
35	Liu Y L , Ai K L , Lu L H . Chem Rev, 2014, 114 (9): 5057
36	Ravikumar A , Panneerselvam P , Morad N . ACS Appl Mater Interfaces, 2018, 10 (24): 20550
37	Lee H , Dellatore S M , Miller W M , et al. Science, 2007, 318 (5849): 426
38	Liang Y , Wei J , Hu Y X , et al. Nanoscale, 2017, 9 (16): 5323
39	Che D D , Cheng J , Ji Z Y , et al. TrAC-Trends Anal Chem, 2017, 97: 1
40	Huang Z , Lee H K . J Chromatogr A, 2015, 1414: 41
41	McCullum C , Tchounwou P , Ding L S , et al. J Agric Food Chem, 2014, 62 (19): 4261
42	Li J Y , Long X Y , Yin H X , et al. J Sep Sci, 2016, 39 (13): 2562
43	Wang Y X , Wang S H , Niu H Y , et al. J Chromatogr A, 2013, 1283: 20
44	Guan W H , Gao X C , Ji G F , et al. J Solid State Chem, 2017, 255: 150
45	Liang Y , Wei J , Hu Y X , et al. Nanoscale, 2017, 9 (16): 5323
46	Zhang M , Zhang X H , He X W , et al. Nanoscale, 2012, 4 (10): 3141
47	Wang Y , Yu L , Lou X W . Angew Chem Int Ed, 2016, 55 (47): 14668
48	Lu W S , Shen Y H , Xie A J , et al. J Magn Magn Mater, 2010, 322 (13): 1828
49	Christus A A B , Panneerselvam P , Ravikumar A , et al. J Photochem Photobiol A:Chem, 2018, 364: 715
50	Qin J N , Wang S B , Wang X C . Appl Catal B:Environ, 2017, 209: 476
51	Sun D T , Peng L , Reeder W S , et al. ACS Cent Sci, 2018, 4 (3): 349
52	Mrowczynski R , Turcu R , Leostean C , et al. Mater Chem Phys, 2013, 138 (1): 295
53	Xu Y J , Tian X H , Zhang X Z , et al. J Chromatogr Sci, 2012, 50 (7): 591
54	Al-Degs Y S , Sweileh J A . Arabian J Chem, 2012, 5 (2): 219
55	Peláez-Cid A A , Blasco-Sancho S , Matysik F M . Talanta, 2008, 75 (5): 1362

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