An Exceptionally Stable TbIII-Based Metal–Organic Framework for

Article Cite This: Inorg. Chem. 2019, 58, 7746−7753

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An Exceptionally Stable TbIII-Based Metal−Organic Framework for Selectively and Sensitively Detecting Antibiotics in Aqueous Solution Qian-Qian Zhu,† Hongming He,*,† Ying Yan,† Jing Yuan,† Di-Qiu Lu,† De-Yu Zhang,† Fuxing Sun,*,‡ and Guangshan Zhu*,§

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†

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, MOE Key Laboratory of Inorganic−Organic Hybrid Functional Material Chemistry, College of Chemistry, Tianjin Normal University, Tianjin 300387, People’s Republic of China ‡ State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, People’s Republic of China § Faculty of Chemistry, Northeast Normal University, Changchun 130024, People’s Republic of China S Supporting Information *

ABSTRACT: An exceptionally stable metal−organic framework based on one-dimensional (1D) TbIII chains with significant green emission under excitation energy, {[Tb(TATMA)(H2O)·2H2O}n (namely, 1), has been fabricated successfully under hydrothermal conditions. By virtue of the spectral overlap between the absorbance spectra of nitrofurans (NFAs) and the excitation spectrum of MOF 1, the resultant sample exhibits outstandingly sensitive and selective luminescence detectability for NFT (Ksv = 3.35 × 104 M−1) and NFZ (Ksv = 3.00 × 104 M−1) by quenching phenomenon. More importantly, it can detect NFAs in water from bovine serum samples. The portable MOF film can be easily prepared and used with excellent stability and recursitivity.

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INTRODUCTION Nitrofurans (NFAs), as a common class of antibiotics with 5nitrofuran rings, have been universally employed to cure bacterial infections and protozoan in humans and animals, especially nitrofurantoin (NFT) and nitrofurazone (NFZ).1,2 Meanwhile, they are also extensively implemented as feed additives for poultry, livestock, and aquaculture to heal bacterial infections (for instance, gastrointestinal enteritis caused by Escherichia coli and Salmonella spp).3,4 Although NFAs have a wide range of applications and splendid therapeutic effects, heavy and uncontrolled misuse of them in humans and animals still aggravates a suite of thorny problems, because of encouragement of the spread of antibiotic resistance of pathogenic bacteria.5−7 Hence, many countries, particularly developed countries, have adopted a total ban on the use of antibiotics, including The United States, Korea, and other nations.3,4 Unfortunately, NFAs are still detected and found in many agricultural products, drinking water, and groundwater, which can infiltrate into human body through the food chains and lead to dozens of diseases.8 Hence, it is extremely important to explore and develop a high-efficiency method or material to accurately detect such antibiotics in water. Many detection techniques have been developed and applied to detect NFAs in recent decades, including gas chromatography coupled with mass spectrometry (GC-MS), liquid chromatography coupled with mass spectrometry (LC© 2019 American Chemical Society

MS), luminescence, and micellar electrokinetic capillary chromatography.9−11 Among all methods, luminescence sensing has attracted significant attention and interest of scientists to consider it as a promising analysis technique in practice, which is mainly attributed to simple operation, celerity, and high sensitivity.12−19 Among various materials, metal−organic frameworks (MOFs), as burgeoning porous inorganic−organic hybrid crystalline materials, are attractive to many scientists in fields of materials science and chemistry, because of their fascinating configurations and widespread applications.20−31 Particularly, lanthanide-based MOFs (Ln-MOFs) have been already used as high-sensitive luminescent solid materials to monitor targeted analytes through luminescent signal response, including spectral shift and intensity change. Compared with other materials, Ln-MOFs reveal various outstanding advantages, such as high color purity, ocular visible color, large Stokes shift, and long luminescent lifetime.32−35 To date, many Ln-MOFs have been successfully prepared and applied to detect small molecules, organic vapor, heavy metal ions, and biomedicine.36−40 However, many Ln-MOFs are still unstable in water, similar to that observed with other MOFs, which is mainly attributed to the weak coordinated bond in the coordinated Received: January 16, 2019 Published: May 29, 2019 7746

DOI: 10.1021/acs.inorgchem.9b00147 Inorg. Chem. 2019, 58, 7746−7753

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Inorganic Chemistry

Cary Eclipse fluorescence spectrophotometer. The morphologies and detailed structure of the ground samples were recorded using a fieldemission scanning electron microscopy (SEM) system (JEOL, Model JSM-6700F). Synthesis of {[Tb(TATMA)(H2O)·2H2O}n (1). Tb(NO3)3·6H2O (20.0 mg, 0.044 mmol) and H3TATMA (10 mg, 0.02 mmol) were both mixed in a 23.0 mL Teflon-lined autoclave with distilled H2O (3 mL) and aqueous NaOH solution (0.01 M, 50 μL). The resultant mixture was subjected to ultrasonic vibration for 10 min at room temperature, then placed in a heating oven at 170 °C for 3 days. The light-yellow block-shaped crystals were generated and collected after cooling to room temperature; these crystals could be directly washed by distilled water and collected for single-crystal X-ray data analysis. The yield is ∼71%, based on H3TATMA. FT-IR (KBr as pellets): 3432 (br), 1627 (s), 1580 (s), 1552 (s), 1525 (s), 1412 (s), 1351 (s), 1305 (s), 1244 (s), 1124 (s), 997 (s), 893 (s), 758 (s), 680 (s), 597 (s), 410 (s) (see Figure S1 in the Supporting Information). Anal. Calcd for C24H21O9N6Tb: C 41.38, H 3.02, N 12.07%; found: C 41.35, H 3.01, N 12.05%. Luminescence Sensing Experiments. Prior to the sensing experiments, the as-synthesized samples were dried in air and further milled using a mortar for ∼5 min. The resultant crystal dispersions of 1 (0.1 mg mL−1) were achieved by placing 3 mg of ground 1 into 30.0 mL of distilled H2O as a stock mixed dispersion, which was subjected to further ultrasonic agitation for 15 min before it was divided into 3mL dispersions. The luminescent intensity can be respectively measured in the absence or presence of different analytes including common antibiotics in aqueous solution (1.0 mM), including nitrofurazone (NFZ), nitrofurantoin (NFT), metronidazole (MDZ), dimetridazole (DTZ), sulfamethazine (SMZ), chloramphenicol (CAP), thiamphenicol (THI), and penicillin (PCL). The structures of these antibiotics are provided in Figure S2 in the Supporting Information. The resultant mixture was further stirred for ∼2 min prior to the luminescence measurement, then the emission spectra intensity was detected immediately. Luminescence titration experiments were measured by collecting the emission intensity of 1 in aqueous solutions at different concentrations of NFZ and NFT, respectively. Recyclable Luminescence Experiments. The reproducibility of MOF 1 for NFZ and NFT was measured in aqueous solution. After the initial quenching experiment, the test material of 1 was recollected by centrifugation and washed with distilled water, which was used in the successive quenching experiment. Single-Crystal X-ray Crystallography. Diffraction intensities for the single-crystal 1 were gathered on a Bruker APEX-II CCD diffractometer with Cu Kα radiation (1.54184 Å) by using a ϕ−ω scan approach. The SADABS program was implemented for the semiempirical multiscan attenuation correction.46 The single-crystal structure can be accurately confirmed by using the direct routine with the SHELXT6 program and refined with full-matrix least-squares technique using the SHELXL-2015 program47−49 through the OLEX2 interface program.50 Anisotropic parameters were measured for all non-hydrogen atoms. The final crystallographic data are contained in Table 1. The selected bond lengths and angles were further provided in Table S1 in the Supporting Information, respectively.

structure. Meanwhile, note that only a few Ln-MOFs have been synthesized and detected antibiotics in aqueous solution.41−43 As a result, it is of great significance to design and prepare ultrastable Ln-MOFs for highly selective and sensitive luminescence sensing for antibiotics in aqueous solution. Hence, we chose and synthesized a semirigid bridging ligand 4,4′,4″-s-triazine-1,3,5-triyltri-m-aminobenzoate (H3TATMA)44,45 (Scheme 1) to further assemble with the Scheme 1. Semirigid Organic Ligand 4,4′,4″-s-triazine-1,3,5triyltri-m-aminobenzoatea

a

Legend: C, black; O, red; N, blue; and H, light gray.

TbIII ion by hydrothermal synthesis to fabricate a threedimensional (3D) material with splendid water stability, {[Tb(TATMA)(H2O)·2H2O}n (namely, 1), which is similar to the reported Eu-based MOF.45 However, experiments involving the Eu-MOF only discuss its catalytic performance for the Knoevenagel condensation reaction. In this work, because of the significant green emission under excitation energy and good dispersibility in the water system, MOF 1 exhibits excellent luminescence detectability for NFT and NFZ in aqueous solution, even in the presence of other interfering antibiotics. Furthermore, it can precisely detect NFAs in water from bovine serum samples. Remarkably, the portable MOF film was easily constructed and performed with excellent stability and recyclability.

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EXPERIMENTAL SECTION

RESULTS AND DISCUSSION Structural Description. From the single-crystal structural result, it clearly illustrated that the three-dimensional (3D) MOF 1 belongs to the triclinic P1̅ space group. As seen in Figure 1a, the asymmetric unit has only one crystallographically independent TbIII ion, two guest H2O solvent molecules, a terminally coordinated H2O molecule, and one completely deprotonated organic linker for charge balance. The totally deprotonated ligand adopts the same coordinated mode as μ5-η1:η1:η1:η2:η1:η2 to link with five TbIII ions (Figure 1b). The coordination bond lengths of Tb−O are in the range of 2.3828(1)−2.6154(1) Å (see Table S1 in the Supporting

Materials and Methods. Chemicals and reagents were purchased as analytical-grade and further used directly. Elemental analysis of C, H and N was performed with a CE-440 analyzer (Leeman Laboratories). A Shimadzu DTG-60A system was used simultaneously to obtain thermogravimetric analysis (TGA) data in the range of room temperature to 800 °C at a heating rate of 10 °C min−1 in N2. Fourier-transform infrared (FT-IR) spectra, KBr as pellets, were recorded from an Avatar-370 (Nicolet) spectrometer from 4000 cm−1 to 400 cm−1. Powder X-ray diffraction (PXRD) profiles were all collected at room temperature on a Rigaku D/max-2500 diffractometer at a sweep speed of 0.2° 2θ min−1. All ultraviolet−visible light (UV-vis) absorption spectra were performed on a Shimadzu Model UV-2700 spectrophotometer. Luminescent data were gained from 7747

DOI: 10.1021/acs.inorgchem.9b00147 Inorg. Chem. 2019, 58, 7746−7753

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profiles, it obviously illustrates that MOF 1 possesses extraordinary stability in the above harsh conditions (see Figure S3 in the Supporting Information), leading to its multiple potential applications in water system. As seen in Figure S4 in the Supporting Information, the TGA data of assynthesized 1 at different temperatures illustrated that the main structure of MOF 1 can be kept well below 370 °C. Furthermore, the framework began to disintegrate rapidly as the heating temperature increased. Selective Sensing for NFT and NFZ. The solid-state luminescence properties of MOF 1 and H3TATMA ligand were both investigated at room temperature. Under excitation energy at 335 nm, 1 demonstrates significantly typical luminescence emission peaks of TbIII at 488, 544, 583, and 620 nm from 5D4 → 7FJ (J = 6−3) transition of TbIII (Figure 2). Especially, the strongest emission band centered at 544 nm

Table 1. Crystal Data and Structure Refinement for 1 parameter

value/comment

compound empirical formula formula weight crystal system space group a b c α β γ V Z ρcalc μ (mm−1) Nref F(000) R(int) goodness-of-fit on F2 R1, wR2 [I > 2σ(I)] R1, wR2 (all data)

1 C24H21O9N6Tb 696.39 triclinic P1̅ 8.1729(4) Å 11.5022(5) Å 14.1731(5) Å 66.304(5)° 74.628(4)° 88.362(4)° 1171.79(11) Å3 2 1.974 g cm−3 15.471 4578 688.0 0.0456 1.042 0.0418, 0.1076 0.0424, 0.1085

Figure 2. Solid-state excitation and emission spectra of 1 at room temperature (inset shows a luminescent photograph of dispersed MOF 1 under irradiation with 365-nm UV light).

comes from a magnetic-dipole-induced 5D4 → 7F5 transition to generate strong green luminescence, which can be utilized as a characteristic signal to monitor the sensing ability for various pollutants in aqueous solution. Under similar conditions, the isolated organic ligand reveals a broad emission peak at 426 nm under exciting at 357 nm, which is approximately ascribed to the π → π* or n → π* transition (Figure S5 in the Supporting Information). In contrast with the emission spectra of H3TATMA and MOF 1, the disappearance of the ligand’s emission peak illustrates that TATMA3− is an excellent antenna linker to sensitize the luminescent property of TbIII ions. Because of the remarkably green luminescence and high stability (Figure S6 in the Supporting Information), it drives us to investigate and explore the luminescence detection capability of MOF 1 to multiple antibiotics in water. The resultant crystal dispersions of ground 1 (0.1 mg mL−1) were achieved and prepared before the measurements. The morphology and dispersion of the ground sample for sensing experiments was measured and observed using SEM tests, illustrating that the sizes of most of the ground samples were others). Notably, the LUMO energy levels of CAP and NFAs are very similar to each other, while MOF 1 has entirely different luminescent quenching responses. The results clearly exhibited that the electron transfer between host and guest is not the unique contributing cause for the luminescence quenching. Meanwhile, the strong absorption bands of NFT and NFZ both significantly overlap with the excitation spectrum of MOF 1 (Figure 9). The excitation energy is easily competitively

Figure 7. Photographs of luminescent film of MOF 1 under (a and c) natural light and (b, d−f) a hand-held ultraviolet lamp (λex = 365 nm), in the presence and absence of NFT aqueous solution (0.5 mM).

for NFT (see Figure S8 in the Supporting Information). As found in Figure 8, the luminescence intensity and quenching

Figure 9. UV−vis absorption spectra of different antibiotics in aqueous solutions.

Figure 8. Recyclability of MOF 1 film with the application of 0.5 mM NFT aqueous solution.

effect of this MOF 1 film can be essentially preserved after applying this film for at least five cycles. These outstanding results indicate that the MOF 1 film can meet the high requirements of authentic detection and recovery for such NFAs antibiotics. Mechanism of Luminescence Quenching. It is remarkably important to understand the luminescence quenching mechanism and highly selective detection capability of MOF 1 to explore and exploit more-efficient materials for the feasible applications. From the previous investigations, it is found that many luminescence quenching phenomena are mainly caused by four representative cases: structure collapse, guest adsorption, host−guest weak interaction, and photocompetitive absorption.59,60 From the PXRD profiles of the reused MOF 1 after 10 cycles (see Figures S9 and S10 in the Supporting Information), it obviously demonstrates that the luminescence quenching is not ascribed to the framework collapse. Second, the no-porous structure and the fast

absorbed by NFZ or NFT molecules to distinctly reduce energy transfer to MOF 1, to produce remarkably luminescent quenching. Therefore, the luminescent quenching of MOF 1 is probably ascribed to the competitive absorption of excitation energy between MOF 1 and antibiotics, especially NFZ and NFT. In addition, the weak intermolecular hydrogen-bonding interactions also may exist between MOF 1 and these antibiotics, thanks to the presence of various hydrogenbonding donors and acceptors.

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CONCLUSION In conclusion, a novel three-dimensional (3D) Tb-MOF with green luminescence has been successfully achieved via hydrothermal methods, illustrating outstanding ultrastability and high selectivity to NFZ and NFT in aqueous solution via naked luminescence quenching. The terminated Ksv values of NFZ and NFT are calculated to be ∼3.0 × 104 and 3.35 × 104 M−1, respectively. More important, MOF 1 can be feasibly 7751

DOI: 10.1021/acs.inorgchem.9b00147 Inorg. Chem. 2019, 58, 7746−7753

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Inorganic Chemistry fabricated into a portable luminescent film to directly monitor NFZ and NFT in aqueous solutions.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.inorgchem.9b00147. FT-IR, TGA, and PXRD patterns (PDF) Video of the luminescent sample (MP4) Video of the luminescent sample (MP4) Accession Codes

CCDC 1887651 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected] (H. He). *E-mail: [email protected] (F. Sun). *E-mail: [email protected] (G. Zhu). ORCID

Hongming He: 0000-0001-5535-8825 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We are grateful to the financial support from the National Natural Science Foundation of China (Nos. 21801187 and 21871105), the Science & Technology Development Fund of Tianjin Education Commission for Higher Education (No. 2017KJ127), and Doctoral Program Foundation of Tianjin Normal University (No. 043135202-XB1702).

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DOI: 10.1021/acs.inorgchem.9b00147 Inorg. Chem. 2019, 58, 7746−7753