Received: 19 March 2019 Revised: 5 May 2019 Accepted: 13 May 2019

FU L L PAP ER

DOI: 10.1002/aoc.5021

Highly sensitive and selective detect of p‐arsanilic acid witha new water‐stable europium metal–organic framework

Chao‐Yang Wang | Huifen Fu | Peng Wang | Chong‐Chen Wang

Beijing Key Laboratory of FunctionalMaterials for Building Structure andEnvironment Remediation/BeijingAdvanced Innovation Centre for FutureUrban Design, Beijing University of CivilEngineering and Architecture, Beijing100044, China

CorrespondenceChong‐Chen Wang, Beijing KeyLaboratory of Functional Materials forBuilding Structure and EnvironmentRemediation/Beijing AdvancedInnovation Centre for Future UrbanDesign, Beijing University of CivilEngineering and Architecture. Beijing100044, China.Email: wangchongchen@bucea.edu.cn

Funding informationBUCEA Post Graduate Innovation Project,Grant/Award Number: PG2019036; Bei-jing Advanced Innovation Centre forFuture Urban Design, National NaturalScience Foundation of China, Grant/Award Number: 21806008; Beijing TalentProject, Grant/Award Number: 2018A35;Project of Construction of InnovationTeams and Teacher Career Developmentfor Universities and Colleges Under Bei-jing Municipality, Grant/Award Number:IDHT20170508; Beijing Municipality Uni-versities, Grant/Award Number:CIT&TCD20180323

Appl Organometal Chem. 2019;e5021.

https://doi.org/10.1002/aoc.5021

The p‐arsanilic acid (p‐ASA), as an aromatic organoarsenic compounds, had

received considerable concerns for their potential toxicity and carcinogenic

properties. It was essential to detect p‐ASA with a facile method. In this paper,

an europium based fluorescent metal–organic framework (MOF)

[Eu2(clhex)·2H2O)]·H2O (BUC‐69) was successfully prepared under hydrother-

mal conditions with 1,2,3,4,5,6‐cyclohexanehexacarboxylic acid (H6clhex) as

organic linker. BUC‐69 displayed superior fluorescence capability to achieve

selective and sensitive detection toward p‐ASA in water, which presented the

first example of a MOF‐based sensor to detect p‐ASA. BUC‐69 showed excel-

lent chemical stability in solutions under pH ranging from 4 to 12, which

makes it be a potential sensor both in acidity and alkalinity condition. Signifi-

cantly, BUC‐69 performed well in fluorescent sensing of p‐ASA at a low con-

centration (10−6 M) in the simulated wastewater prepared with real lake

water, and the results were comparable to the values detected by Inductively

Coupled Plasma Optical Emission Spectrometer (ICP‐OES). The corresponding

mechanism of fluorescent sensing toward p‐ASA with BUC‐69 was proposed

and affirmed.

KEYWORDS

fluorescence, metal–organic framework, p‐arsanilic acid, sensing, water stability

1 | INTRODUCTION

Arsenic compounds were widely presented in differentenvironments like soil, rivers, lakes, oceans and evenair, which poses various severe problems to ecologicalsystem.[1] As one of organoarsenic compounds or aro-matic organoarsenicals, p‐arsanilic acid (p‐ASA) is widelypresented in water along with soil, and it has been con-sidered to be an emerging micropollutant.[1–4] In the pastdecades, p‐ASA was heavily used as feeds additives for

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poultry and swine to promote growth, prevent/treat dys-entery and control intestinal parasites,[5] which aroseconcerns about public health.[4] It was reported that p‐ASA were metabolized by animals and discharged viaurine and manure in the unchanged form, and the p‐ASA would be degraded into highly toxic inorganic arse-nic species (such as arsenate) in 30 d, which exerted aserious threat to the safety of soil and groundwater.[1,4]

Generally, the p‐ASA in environment was concen-trated and quantitatively determined by HPLC‐ICP‐

© 2019 John Wiley & Sons, Ltd./journal/aoc 1 of 8

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MS.[4,6,7] However, HPLC‐ICP‐MS is high‐cost, non‐portable and time consuming, which limited the real‐time monitoring of p‐ASA. Therefore, a rapid and visualsensor for selectively detect of p‐ASA is essential forreal‐time monitoring, as the rapid and visual fluorescentsensors have been increasingly popular for their high sen-sitivity, rapid response, simple operation, and low cost.[8]

In last two decades, metal–organic frameworks(MOFs) arose increasing interests from researchers fortheir diverse structure characters like large surface area,nanoscale channels, topological diversities.[9,10] and theirpotential applications like gas adsorption/separation,[11–14] photocatalysis,[15–20] gas storage,[21–23] drug deliv-ery,[24,25] and sensor.[26–30] Lanthanide MOFs (Ln‐MOF)as fluorescent probes for sensing pollutants have receivedparticular attentions owing to their higher quantumyield, excellent optical properties, easy miniaturizationand non‐invasive properties.[28,31,32] Up to now, fluores-cent Ln‐MOFs were used to detect different heavy metalions,[29] nitroaromatic explosives,[33] volatile organiccompounds (VOCs),[34,35] pH,[28] uric acid (2,6,8‐trihydroxypurine, UA),[36] and biogenic amines (BAs)[37]

in organic solvents, aqueous solutions and evenatmosphere.[28,29,37,38]

According to previous reports, detections of inorganicarsenic like As (III) with the aid of fluorescent MOFhad been reported.[39] However, to the best of ourknowledge, there was no report concerning the fluores-cent sensing p‐ASA in MOFs. With this paper, a newthree‐dimensional Eu‐MOF BUC‐69 was synthesizedand then used as fluorescent sensor to selectively detectp‐ASA in aqueous solution. The results revealed thatBUC‐69 exhibits excellent p‐ASA determination activitywith high sensitivity and selectivity in presence of differ-ent co‐existing metal ions in aqueous solution. Also,BUC‐69 displayed excellent outstanding stability underpH values ranging from 4.0 to 12.0 and remarkablewater stability (40 days in water), which makes it poten-tially useful for practical samples. Finally, the corre-sponding mechanism of fluorescent detect toward p‐ASA was proposed.

2 | EXPERIMENTAL

2.1 | Synthesis

[Eu2(clhex)·2H2O)]·H2O (BUC‐69) was hydrothermallysynthesized by mixing EuCl3·6H2O (0.3 mmol, 0.1099 g),H6clhex (0.3 mmol, 0.1045 g), deionized water (7 ml)and DMF (7 ml) with a molar ratio of 1:1:1296:1296, thenthe solution was sealed in a 25 ml Teflon‐lined stainlesssteel reactor, heated at 140 °C for 72 hr. After the

hydrothermal reaction, slowly cooled down to room tem-perature. White block‐like crystals of BUC‐69 were pro-duced with the yield of 88% based on EuCl3·6H2O, thenthe crystals were washed by deionized water and ethanol.Anal. Calc. for BUC‐69, C12H12Eu2O15, C, 20.57%; H,1.71%; O, 34.28%. Found: C, 20.55%; H, 1.72%; O,34.29%. IR (KBr)/cm‐1: 3390, 1594, 1417, 1334, 1304,1264, 930, 824, 706, 618, 509, 451.

2.2 | Stability

BUC‐69 (4.0 mg) were suspended into 4 ml of water solu-tion with different pH values and oscillated for 10 s, thenfluorescence spectra were recorded after 5 min equilibra-tion in the cuvettes. The pH of water solution wasadjusted by using HCl or NaOH (10−2 M), respectively.Also, the BUC‐69 powder was collected after being fil-tered from the solution and being dried under air to con-duct PXRD determination.

2.3 | Fluorescent determination oforganic solvents with BUC‐69

BUC‐69 (4.0 mg) were suspended into 4 ml of organic sol-vents (ethanol, methanol, acetonitrile, tetrahydrofuran,trichloromethane, N,N‐dimethylformamide (DMF), andacetone) and oscillated for 10 s, then fluorescence spectrawere recorded after 5 min equilibration time in thecuvettes.

2.4 | Fluorescent determination of metalions with BUC‐69

In order to identify the sensing ability of BUC‐69 towardvarious metal ions, 4 mg BUC‐69 were simply soaked inaqueous solutions containing 10−3 M MClx (M = Na+,K+, Mg2+, Ca2+, Ba2+, Cr3+, Mn2+, Co2+, Ni2+, Cu2+,Ag+, Zn2+, Cd2+, Al3+, Fe2+ and Pb2+. After being oscil-lated for 10 s and standing for 5 min to achieve equilibra-tion, the fluorescence emission spectra of BUC‐69 wererecorded at λex = 250 nm.

2.5 | Fluorescent determination of p‐ASAwith BUC‐69

BUC‐69 (4.0 mg) were suspended into 4.0 ml of aqueoussolutions with different p‐ASA concentrations, respec-tively. The mixtures were oscillated for 10 s and equili-brated in the cuvettes for 5 min, then the fluorescencespectra were recorded at λex = 250 nm.

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3 | RESULTS AND DISCUSSIONS

3.1 | Crystal structure description

The asymmetric unit of 3D BUC‐69 consists of one Eu3+

cation, one full deprotonated cyclohexane‐1,2,3,4,5,6‐hexacarboxylate anion (clhex6−), three aqua ligandsand one lattice water molecules. As illustrated inFigure 1, the protonated clhex6− anions adopt the e,e,e,e,e,e‐conformation (Scheme S1 (a)), in which the cen-tral ring exhibits the chair‐shaped configuration andthe six carboxylate groups are located at the equatorialpositions. The protonated cyclohexane‐1,2,3,4,5,6‐hexacarboxylate anions exhibit a μ6‐L

II coordinationmode (Scheme S1). In detail, the carboxyl groups ofclhex6− anions are engaged in coordination to theEu3+ ions, which displayed three different coordinationmodes: (1) the O3‐C2‐O4 carboxylate group chelatingone Eu3+ ion; (2) the O5‐C3‐O6 carboxylate groupmonoatomically bonded to one Eu3+ ion; (3) the O1‐C1‐O2 carboxylate group bridging two Eu3+ ions.[40]

The Eu3+ atoms are nine‐coordinated by six oxygen

FIGURE 1 (a) Highlight of the coordination polyhedron for the Eu

network of BUC‐69; (d) The 3D structure of BUC‐69

atoms from four clhex6− anions and three oxygen atomsfrom three different ligands to complete a distortedtricapped trigonal prism. The Eu‐O distances to the cap-ping oxygen atoms fall in the range of 2.486(10)‐2.501(9)Å, and those to the prism corners in the region of2.379(9)‐2.547(10) Å. In BUC‐69, Eu3+ centers are inter-connected by the μ6‐L

II clhex6− anions (Scheme S1 (b)),leading to a 2D metal–organic layers (Figure 1 (c)),which extended two infinitely parallel to a (0 1 0) and(1 1 0), respectively. The two layers are perpendiculareach other to construct three‐dimensional framework,in which its two adjacent Eu atoms connected bybidentate bridging carboxylates group can be consideredas [Eu2(H2O)2] dimers. The Eu3+ atoms in the adjacentlayers are joined by two deprotonated clhex6− ligandsin monodentate mode and one coordination water mol-ecule along the (0 1 0) and (1 1 0) direction to accom-plish a three‐dimensional framework (Figure 1 (d)). Inaddition, the 3D structure of BUC‐69 was further stabi-lized by the hydrogen bonding interactions (O6‐H6C···O2, O6‐H6D···O3 and O6‐H6D···O1) between themonodentate carboxylic O‐atom(O6) and the chelating

(III) atom; (b) The secondary building unit of EuO9; (c) The 2D

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carboxylic O‐atom (O1, O3) attached on the carboxylategroup of clhex6‐ ligand (Table S3).

3.2 | Fluorescence properties

As expected, BUC‐69 demonstrated distinct red fluores-cence under UV‐light excitation (Figure 2), which isascribed to “antenna effect” of H6clhex ligand.[40,41] Theexcitation spectrum of BUC‐69 was measured at theemission of 616 nm, which was dominated by severalbroad bands centered at about 318 nm, 326 nm,361 nm, 366 nm, 375 nm, 380 nm and 394 nm. The emis-sion spectrum of BUC‐69 (solid‐state) were performed inthe range of 200–800 nm (Ex = 394 nm) at ambient tem-perature (298 K), in which the five sharp peaks character-istic of Eu3+ ions cantered at 580, 591, 616, 651, and700 nm are assigned to the 5D0 → 7F0,

5D0 → 7F1,5D0 →

7F2,5D0 →

7F3, and5D0 →

7F4 transitions, respec-tively.[41] The weak peak at 580 nm and 651 nm areregarded as both strictly forbidden in magnetic‐dipole(MD) and electric dipole (ED) schemes.[42] The stronger5D0 →

7F1 transition is attributed to a MD‐allowed transi-tion. The transitions of 5D0 →

7F0 and5D0 →

7F3 are for-bidden both in magnetic and electric dipole schemes,which also make the emission bands at 580 and 651 nmare weaker.[43] As shown in Figure 2, the emission inten-sity at 616 nm is strongest, which should mostly belong tothe electric dipole (ED) transition.[43] A highly polariz-able chemical environment around the Eu3+ ions aremade by the strong transitions of 5D0 → 7F2.

[44] Hence,a light red emission of BUC‐69 appeared under the exci-tation of 394 nm.

FIGURE 2 Emission spectrum of BUC‐69 in solid state at room

temperature (Ex = 394 nm, the inset shows the excitation

spectrum of BUC‐69)

3.3 | Selective sensing detection activity ofBUC‐69 toward p‐ASA

The obtained powder X‐ray diffraction patterns of BUC‐69 matched well with the simulated patterns from thesingle‐crystal X‐ray diffraction data, indicating thatBUC‐69 was in high purity (Figure S1). The structure ofBUC‐69 is water‐stable, as evidenced by PXRD of thesample dispersed for 40 d in water (Figure S1). BUC‐69displayed excellent pH stability in water at different pH,confirmed by PXRD (Figure S5). As illustrated in FigureS6, the fluorescence of BUC‐69 exhibited minor pH inde-pendent in the pH range of 4.0–12.0, which indicated thatthe fluorescence of BUC‐69 was free of the pH influence.In addition, the fluorescence effected by solvents was fur-ther studied, the results (Figure S7) showed that mostorganic solvents have little effect on the emission inten-sity of BUC‐69 except acetone and DMF. As shown inFigure S8, the fluorescence intensity of the suspensionsignificantly decreased with the addition of acetone andDMF. Based on the Stern‐Volmer model equation fittingand calculation, it was found that the LOD of BUC‐69toward acetone and DMF are 0.06% and 0.87% (vol%),respectively, which were further translated to molar con-centration are 79.49 mM and 0.11 M.

In order to investigate the quenching mechanism ofacetone and DMF, the PXRD of BUC‐69 were measured(Figure S9). The results showed that the frameworkremains intact in acetone and DMF, and the quenchingeffect is not caused by structure collapsed. To furtherinvestigate the mechanism for the quenching effect ofacetone and DMF, the UV–vis spectra and excitationspectrum were recorded (Figure S10). The resultsrevealed that the excitation spectrum of the BUC‐69was almost be overlapped by the absorption spectra ofacetone and DMF, while the similar overlap at wave-length range of 200 nm ‐ 300 nm can't be found betweenBUC‐69 and other solvents. In other words, both acetoneand DMF adsorb the excitation energy of BUC‐69 todecrease the energy transfer efficiency from the H6lhexto the Eu3+ ions, resulting into the fluorescencequenching.[45–47]

On the basis of the aforementioned fluorescence stabil-ity studies in broad pH regions and solvents effect onemission spectra of BUC‐69, the effects of different metalions were further investigated (Figure 3). It is observedthat, most of metal ions have minor or no fluorescencevariations effect on the emission intensity of BUC‐69.To further investigate the fluorescence quenchingeffected by p‐ASA, concentration‐dependent studies wereperformed by the gradual addition of p‐ASA to a deion-ized water suspension of BUC‐69. As shown in Figure 4(a), the emission intensity of BUC‐69 suspension declines

FIGURE 3 (a) Emission spectra of BUC‐69 treated with different metal ions (10−3 M), and (b) Emission intensity of BUC‐69 at 615 nm in

aqueous solutions

FIGURE 4 (a) Emission spectra and intensities for BUC‐69 dispersed in a series of concentration solution of p‐ASA (H2O) (inset: the inset

shows the fluorescence intensities for BUC‐69 at 615 nm (Ex = 250 nm), (b) The excitation spectrum of BUC‐69 and UV–vis absorption

spectrum of p‐ASA

WANG ET AL. 5 of 8

gradually with the increase of p‐ASA concentration from0 to 40 μM, and the fluorescence quenching efficiencywas quantitatively analysed by using the Stern‐Volmerequation (1):[48,49]

I0I¼ 1þ Ksv Q½ � (1)

Where, Ksv is the quenching constant, [Q] is the p‐ASAconcentration, and the values I0 and I are the fluorescenceintensity of theBUC‐69 suspension without andwith addi-tion of p‐ASA, respectively. As shown in Figure 4 (a), thelinear correlation coefficient (R2) of Ksv curve is 0.9985,suggesting that the quenching effect of p‐ASA on the fluo-rescence of BUC‐69 fits the Stern‐Volmer model well, andBUC‐69 can be potentially used as sensor to achieve thequantitative determination of p‐ASA. The calculated Ksv

value is 0.0122, implying an effective quenching effect of

p‐ASA on theBUC‐69 fluorescence.[50,51] As well, the limitof detection (LOD) can be calculated from the ratio of 3δ/S,in which S is the slope of the fitting line and δ is standarddeviation for 11 replicating fluorescence measurements ofblank solutions. In this study, Ksv is 0.0122 and δ is0.0073, therefore, the LOD ofBUC‐69 toward p‐ASA is cal-culated as 1.81 μM,[46,52] implying that BUC‐69 can bepotentially used to detect p‐ASA in real wastewater. Con-sidering that the different forms of p‐ASA were presented(2.0 < pH < 4.1 neutral p‐ASA, 4.1 < pH < 9.2 anionicASA−, pH > 9.2 anionic ASA2−) under different pH condi-tions,[53,54] further experiments were conducted in acidicand alkalinous environment (pH= 4.0 and 12.0) to investi-gate the sensing performances towards p‐ASA. As shownin Figure S11, p‐ASA can be detected effectively by BUC‐69 under both acidic and alkalinous conditions. The results

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exhibited that BUC‐69 is sensitive to p‐ASA under bothconditions of pH = 4 and pH = 12.

Considering that the co‐existing metal ions in realsamples are potential interfering factors to influence thefluorescent sensing of MOFs,[47] it is necessary to investi-gate whether BUC‐69 can act as a highly selective sensortoward p‐ASA in presence of different co‐existing metalions like K+, Na+, Ag+, Mg2+, Ca2+, Mn2+, Co2+, Ni2+,Cu2+, Cd2+, Zn2+, Fe2+, Al3+, Cr3+, Ba2+, Ag+ and Pb2+

(10−3 M). As shown in Figure 3(b), the fluorescenceintensity of BUC‐69 exhibited minor quenching effect inthe presence of selected co‐existing metal ions, while itexhibited significant quenching effect in the presence ofp‐ASA in the system, which confirmed that BUC‐69could be used as a selective sensor for p‐ASA detectionin aqueous solution. Considering that the co‐existenceof As (III) and p‐ASA in the water environment, thedetection effect of As (III) with BUC‐69 has been com-pared to p‐ASA. The results (Figure S12) revealed thatBUC‐69 exhibited imperceptible quenching effect in thepresence of As (III) (10−3 M). In contrast, the fluores-cence of BUC‐69 was completely quenched toward p‐ASA solution with the identical concentration. It exhib-ited the high selectivity of BUC‐69 toward p‐ASA inaqueous solution.

To further evaluate the possibility of using BUC‐69 assensor to detect the p‐ASA in real wastewater, the surfacewater (Minghu lake in Daxing campus, Beijing Universityof Civil Engineering and Architecture, the common ionsin the lake water and their concentrations were listed inTable S4) was used to prepare the simulated wastewaterwith different p‐ASA concentrations. As listed in TableS5, all measured results matched perfectly with theestablished p‐ASA concentrations, which can be compa-rable with the measured concentration by ICP‐OES(ICP‐500, Focused Photonics Inc) detection results,

FIGURE 5 (a) Emission spectra of BUC‐69 in recycling experimen

Fluorescence intensity of BUC‐69 in recycling experiments for detecting

indicating that BUC‐69 can be practically used to quanti-tatively detect p‐ASA in real wastewater samples.

The recyclability and reusability ofBUC‐69 as a fluores-cent sensor was further explored. As shown in Figure 5,when dispersed in 10−3 M of p‐ASA for suspension, BUC‐69 exhibited the same degree of fluorescence quenchingeffect after each cycle. Also, the fluorescence intensitycan be recovered to the identical level when the systemwas changed to deionized water. The framework of BUC‐69 is still well maintained after 5 runs' use, which can beaffirmed by the PXRD (Figure S13). Based on the aboveresults, BUC‐69 has a great potential as a sensitively andselectively fluorescent sensor toward p‐ASA.

3.4 | Mechanism

It is well‐known that the mechanisms for the fluorescencequenching behavior of MOFs induced by analyte throughthe following three interactions: long range, short range,and complex/collision‐driven.[45] Radiative energy trans-fer is long range (and range‐independent) interactions, inwhich the emission energy from the probe material andexcitation energy can be competitive absorption by analytespecies (photo‐competitive effect), resulting apparentemission quenching of the fluorescent materials.[45,55] För-ster resonance energy transfer (FRET, short range interac-tions), and Dexter electron exchange (DEE,overlap/collision interactions) and Photoinduced electrontransfer (PET, overlap/collision interactions) are alsowidely used in exploring the quenching behavior of fluo-rescent MOFs.[12,45]

The BUC‐69 treated with p‐ASA aqueous solution(10−3 M) has the same PXRD pattern with the simulatedand pristine BUC‐69 (Figure S10), indicating that the fluo-rescence quenching is not induced by its framework

ts employing it as a fluorescence sensor for detecting p‐ASA; (b)

p‐ASA

FIGURE 6 The UV–vis spectra of BUC‐69, BUC‐69 & p‐ASA,

ASA (inset: the inset shows the UV–vis spectrum for BUC‐69

WANG ET AL. 7 of 8

collapse.[28] As shown in Figure 4b, the strong UV–visabsorption band of p‐ASA ranging from 200 nm to300 nm was overlapped with the excitation spectrum ofthe BUC‐69 (Em = 615 nm), which indicates that thistransduction mechanisms may be the reason of radiativeenergy transfer quenching emission. The UV–vis absorp-tion band of p‐ASA has none overlap band with the emis-sion characteristic band of BUC‐69 at 580, 591, 616, 651,and 700 nm (Figure 4b), demonstrating that there wasnone Förster resonance energy transfer (FRET) existingin the quenching emission process. No obvious red shiftor blue shift were found the UV–vis absorption peak ofBUC‐69 when contact with p‐ASA in the suspension(Figure 6a), implying that there is no PET or DEE interac-tions in the system.[56,57] All these findings further con-firmed that the sensing mechanism could be assigned tothe radiative energy transfer process. The fluorescentdecay curves of the BUC‐69 suspensions with and withoutp‐ASA (10−4M)were investigated. As shown in Figure S14,the similar excited‐state lifetime of two different analystsindicated that the quenching process of p‐ASA wasascribed to static quenching mechanism.[58,59]

4 | CONCLUSIONS

In summary, a new water stable Eu‐MOF comprisingflexible H6clhex ligand have been successfully synthe-sized. BUC‐69 exhibited strong guest‐dependent fluores-cent behavior for small molecules, particularly foracetone and DMF. It exhibited high selectivity and sensi-tivity for sensing p‐ASA with a LOD of 1.81 μM, and itcould be reused at least five times without any

interference in its sensing activity. Further, BUC‐69 per-formed well in sensing p‐ASA in natural aqueous solutionwith various co‐existing ions. The excellent performanceon selective detection of p‐ASA and other small mole-cules make it be an effective real time sensor in thefuture. Further studies should be conducted to modify,composite and morphological control, which mayenhance their stability and sensitivity.

ACKNOWLEDGEMENTS

This work was supported by Great Wall Scholars TrainingProgram Project of Beijing Municipality Universities(CIT&TCD20180323), Project of Construction of Innova-tion Teams and Teacher Career Development for Univer-sities and Colleges Under Beijing Municipality(IDHT20170508), Beijing Talent Project (2018A35), Bei-jing Advanced Innovation Centre for Future UrbanDesign, National Natural Science Foundation of China(21806008), BUCEA Post Graduate InnovationProject(PG2019036).

ORCID

Chong‐Chen Wang https://orcid.org/0000-0001-6033-7076

REFERENCES

[1] X. Liu, W. Zhang, Y. Hu, E. Hu, X. Xie, L. Wang, H. Cheng,Chemosphere 2015, 119, 273.

[2] J. C. Saha, A. K. Dikshit, M. Bandyopadhyay, K. C. Saha, Rev.Env. Sci. Tec. 1999, 29, 281.

[3] F. T. Jones, Poult. Sci. 2007, 86, 2.

[4] L. Wang, H. Cheng, Environ. Sci. Technol. 2015, 49, 3473.

[5] B. P. Jackson, J. C. Seaman, P. M. Bertsch, Chemosphere 2006,65, 2028.

[6] X. Liu, W. Zhang, Y. Hu, H. Cheng,Microchem. J. 2013, 108, 38.

[7] J. J. Sloth, E. H. Larsen, K. Julshamn, J. Anal. Atom. Spectrom.2003, 18, 452.

[8] J. Xie, Y.Wang,W. Liu, X. Yin, L. Chen, Y. Zou, J. Diwu, Z. Chai,T. E. Albrecht‐Schmitt, G. Liu, Angew. Chem. 2017, 129, 7608.

[9] H. Furukawa, N. Ko, Y. B. Go, N. Aratani, S. B. Choi, E. Choi,A. O. Yazaydin, R. Q. Snurr, M. O'Keeffe, J. Kim, Science 2010,329, 424.

[10] C. C. Wang, Y. S. Ho, Forensic Sci. 2016, 109, 1.

[11] Z. Kang, J. Ding, L. Fan, X. Ming, D. Zhang, L. Gao, S. Qiu,Inorg. Chem. Commun. 2013, 30, 74.

[12] J. J. Li, C. C. Wang, H. F. Fu, J. R. Cui, P. Xu, J. Guo, J. R. Li,Dalton Trans. 2017, 46, 10197.

[13] M. S. Denny, S. M. Cohen, Angew. Chem. 2015, 127, 9157.

[14] X. Y. Xu, C. Chu, H. Fu, X. D. Du, P. Wang, W. Zheng, C. C.Wang, Chem. Eng. J. 2018, 350, 436.

8 of 8 WANG ET AL.

[15] C. C. Wang, J. R. Li, X. L. Lv, Y. Q. Zhang, G. Guo, Energ. Envi-ron. Sci. 2014, 7, 2831.

[16] A. D. Z. Kang y, A. M. Asiri, H. García, Angew. Chem. 2016, 55,5414.

[17] L. Rui, S. Lijuan, R. Zhuyun, W. Weiming, T. Yanxi, F. Hongru,Z. Jian, W. Ling, Chem. Commun. 2014, 50, 8533.

[18] C. C. Wang, X. D. Du, J. Li, X. X. Guo, P. Wang, J. Zhang, Appl.Catal. B‐Environ. 2016, 193, 198.

[19] X. Du, X. Yi, P. Wang, J. Deng, C. C. Wang, Chinese J. Catal.2019, 40, 70.

[20] X. D. Du, X.‐H. Yi, P. Wang, W. Zheng, J.‐G. Deng, C.‐C. Wang,Chem. Eng. J. 2019, 356, 393.

[21] S. Nandi, L. P. De, T. D. Daff, J. Rother, M. Liu, W. Buchanan,A. I. Hawari, T. K. Woo, R. Vaidhyanathan, Sci. Adv. 2015, 1,e1500421.

[22] E. C. Spencer, J. Eckert, O. M. Yaghi, Science 2005, 309, 1350.

[23] N. L. Rosi, J. Eckert, M. Eddaoudi, D. T. Vodak, J. Kim, M.O'keeffe, O. M. Yaghi, Science 2003, 300, 1127.

[24] P. Szuromi, Science 2016, 353, 883.

[25] H. Patricia, C. Tamim, S. Christian, G. Brigitte, S. Catherine, B.Tarek, J. F. Eubank, H. Daniela, C. Pascal, K. Christine, Nat.Mater. 2010, 9, 172.

[26] M. Pan, Y. X. Zhu, K. Wu, L. Chen, Y. J. Hou, S. Y.Yin, H. P. Wang, Y. N. Fan, C. Y. Su, Angew. Chem. 2017,129, 14774.

[27] S. N. Zhao, L. J. Li, X. Z. Song, Z. Min, Z. M. Hao, M. Xing, L.L. Wu, F. Jing, S. Y. Song, W. Cheng, Adv. Funct. Mater. 2015,25, 1463.

[28] X. Z. Song, S. Y. Song, S. N. Zhao, Z. M. Hao, Z. Min, M. Xing,L. L. Wu, H. J. Zhang, Adv. Funct. Mater. 2014, 24, 4034.

[29] R. I. Khan, A. Ramu, K. Pitchumani, Sensors Actuat. B‐Chem.2018, 266, 429.

[30] H. Fu, X. Wang, P. Wang, Z. Wang, H. Ren, C. C. Wang, DaltonTrans. 2018, 47, 9014.

[31] X. Chen, T. Pradhan, F. Wang, J. S. Kim, J. Yoon, Chem. Rev.2012, 112, 1910.

[32] L. E. Kreno, K. Leong, O. K. Farha, M. Allendorf, R. P. V.Duyne, J. T. Hupp, Chem. Rev. 2012, 112, 1105.

[33] S. S. Nagarkar, B. Joarder, A. K. Chaudhari, S. Mukherjee, S. K.Ghosh, Angew. Chem. Int. Ed. 2013, 52, 2881.

[34] Y. Zhou, B. Yan, Chem. Commun. 2016, 52, 2265.

[35] J. N. Hao, B. Yan, Nanoscale 2016, 8, 12047.

[36] X. Lian, B. Yan, Inorg. Chem. 2017, 56, 6802.

[37] X. Y. Xu, X. Lian, J. N. Hao, C. Zhang, B. Yan, Adv. Funct.Mater. 2017, 29, 1702298.

[38] S. S. Zhao, J. Yang, Y. Y. Liu, J. F. Ma, Inorg. Chem. 2016, 55,2261.

[39] S. K. Vaishanav, J. Korram, P. Pradhan, K. Chandraker, R.Nagwanshi, K. K. Ghosh, M. L. Satnami, J. Fluoresc. 2017, 27,781.

[40] C. Y. Wang, B. Yu, H. Fu, P. Wang, C. C. Wang, Polyhedron2019, 59, 298.

[41] S. Zhang, Y. Yang, Z. Q. Xia, X. Y. Liu, Q. Yang, Q. Wei, G. Xie,S. P. Chen, S. L. Gao, Inorg. Chem. 2014, 53, 10952.

[42] D. R. Ambili, S. Biju, M. L. Reddy, Inorg. Chem. 2008, 47, 8091.

[43] M. H. V. Werts, R. T. F. Jukes, J. W. Verhoeven, Phys. Chem.Chem. Phys. 2002, 4, 1542.

[44] Z. Hao, X. Song, Z. Min, M. Xing, S. Zhao, S. Su, W. Yang, S.Song, H. Zhang, J. Mater. Chem. A 2013, 1, 11043.

[45] W. P. Lustig, S. Mukherjee, N. D. Rudd, A. V. Desai, J. Li, S. K.Ghosh, Chem. Soc. Rev. 2017, 46, 3242.

[46] J. Liu, G. Ji, J. Xiao, Z. Liu, Inorg. Chem. 2017, 56, 4197.

[47] H. Weng, B. Yan, Anal. Chim. Acta 2017, 988, 89.

[48] S. M. Aly, M. R. Parida, A. Erkki, O. F. Mohammed, Chem.Commun. 2014, 50, 10452.

[49] A. A. O. El‐Ballouli, A. Erkki, B. Marco, S. M. Aly, A. P.Lagrow, O. M. Bakr, O. F. Mohammed, J. Am. Chem. Soc.2014, 136, 6952.

[50] A. Nitzan, J. Jortner, J. Kommandeur, E. Drent, Chem. Phys.Lett. 1971, 9, 273.

[51] C. Liu, B. Yan, Photochem. Photobiol. Sci. 2015, 14, 1644.

[52] H. Ji‐Na, Y. Bing, Chem. Commun. 2015, 51, 7737.

[53] W.‐R. Chen, C.‐H. Huang, J. Hazard. Mater. 2012, 227, 378.

[54] S. Zheng, Y. Cai, K. E. O'Shea, J. Photoch. Photobio. A 2010,210, 61.

[55] C. Guo, Q. Jin, Y. Wang, B. Ding, Y. Li, J. Huo, X. Zhao, SensorActuators B: Chem. 2016, 234, 184.

[56] H. Y. Li, Y. L. Wei, X. Y. Dong, S. Q. Zang, T. C. W. Mak, Chem.Mater. 2015, 27, 1327.

[57] J. J. Liu, Y. B. Shan, C. R. Fan, M. J. Lin, C. C. Huang, W. X.Dai, Inorg. Chem. 2016, 55, 3680.

[58] C. Guo, Q. Jin, Y. Wang, B. Ding, Y. Li, J. Huo, X. Zhao, Sen-sors Actuat. B‐Chem 2016, 234, 184.

[59] H. A. Azab, G. M. Khairy, R. M. Kamel, Spectrochim. Acta A2015, 148, 114.

SUPPORTING INFORMATION

Additional supporting information may be found onlinein the Supporting Information section at the end of thearticle.

How to cite this article: Wang C‐Y, Fu H, WangP, Wang C‐C. Highly sensitive and selective detectof p‐arsanilic acid with a new water‐stableeuropium metal–organic framework. ApplOrganometal Chem. 2019;e5021. https://doi.org/10.1002/aoc.5021