Fabrication of a 3D supramolecular Cd(II)-coordination polymer as a luminescent sensor for detection of sulfamethazine

doi:10.21203/rs.3.rs-1715020/v1

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Fabrication of a 3D supramolecular Cd(II)-coordination polymer as a luminescent sensor for detection of sulfamethazine

https://doi.org/10.21203/rs.3.rs-1715020/v1

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A 3D supramolecular coordinated polymer with formula [Cd₂(L)₂(bib)(H₂O)₂] (1) (H₂L = 4,4’-(1,2-phenlenebis(methyleneoxy))dibenzoic acid and bib = 1,4- bis(1-imidazoly)benzene), has been synthesized and characterized. A one-dimensional (1D) chain structure of 1 with poly-rotaxane was confirmed by a single crystal X-ray approach. This structure was woven for reaching a 3D supramolecular architecture held by hydrogen-bonded and packing intermolecular interactions between adjacent motifs. The luminescence sensing experiments indicates that it is a fluorescent sensor for the detection of antibiotics in 1. It is a highly sensitive/selective polymer towards sulfamethazine (SMZ) that revealed a low detection limit of 1.05 ppm with a high K_SV value of 2.98 × 10³ M^− 1. Its antibiotics sensing mechanism was also studied by theoretical calculations.

Coordination polymers

Antibiotic sensor

Supramolecular interactions

DFT

A new 3D supramolecular Cd(II) coordination polymer (CP) was synthesized
The CP was characterized using different physico-chemical techniques.
Antibiotics sensing capability was demonstrated for the CP.
The CP was shown to be a good sensor for antibiotic sulfamethazine.

Sulfonamides are preventive and therapeutic medicines to treat infections with wide use used in humans, livestock, and aquaculture for infection protection as well as for promoting growth [1]. Their overuse, commonly for cultivating the animal industry has been related to their low cost and good drug potential. Based on the toxicology experiments, an animal's antibacterial resistance has been proven by an excessive sulfonamide as an animal-based foodstuff additive [2]. Therefore, it is not only important but, also a challenge for designing a stable sensitive indicator with high applicability that can be capable of detecting polytypic antibiotics in an aqueous medium [3]. Various sensitive and selective technologies such as electrochemistry, chromatography (HPLC: high-performance liquid chromatography), ion mobility spectrometry (IMS), etc., have been reported for detecting the antibiotics in past decades [4–6]. Due to their drawbacks such as ex-situ and cumbersome, needing long preparation time, etc., finding novel ways to detect antibiotics is a great research field.

Until now, most luminescent coordination polymers (LCPs) based sensors with fluorescence quenching future via both electron or energy transfer from sensor to guest have been reported [7–10]. Thus, it is an effective procedure for synthesizing a suitable luminophore by directional synthesis of the linkers with photosensitive characteristics [11–13]. An enhanced luminescence quenching property can be reached for the frameworks containing some special functional groups of the pyridine ring, amide groups, and –OH [14–15]. In light of the considerations, as the multicarboxylate and N-containing co-ligands, 4,4’-(1,2-phenlenebis(methyleneoxy)dibenzoic acid (H₂L) and 1,4- bis(1-imidazoly)benzene (bib) have been employed to form LMOFs due to the following consideration [16–17]: (a) To reach an enhanced fluorescence intensity, more rigid linker with a longer conjugated system is required; (b) Diversified topological motifs can be achieved via the interaction of metallic cations with the H₂L as ligand because of the presence of many versatile carboxylic acid functional groups providing multiple coordination centers.

According to the discussion mentioned above, we fabricated a novel luminescent coordination polymer (LCP), with the formula [Cd₂(L)₂(bib)(H₂O)₂] (1). The LCP was used as a sensor for detecting antibiotics. Also, LCP’s anti-interference sensing capability and good recyclability have been explored. The most significant findings of these studies are depicted here. Furthermore, in the study of the detection mechanism, the critical role was related to the photoinduced electron transfer and the competition absorption.

2.1 Materials and Method

All chemicals/reagents used were analytical grade in purity and used as purchased. Powder X-ray diffraction (PXRD) patterns/data were achieved by a Bruker ADVANCE X-ray diffractometer (source: Cu-Kα radiation (λ = 1.5418 Å), accelerating voltages: 50 kV, 20 mA, scan rate: 6°/min, step size: 0.02°). Thermogravimetric analysis (TGA) was done at an N₂ ambient (heating rate: 10°C min^− 1).

2.2 Synthesis of [Cd₂(L)₂(bib)(H₂O)₂] (1)

A mixture of H₂L (0.15 mmol, 0.057 g), bib (0.25 mmol, 0.053 g), Cd(NO₃)₂·4H₂O (0.4 mmol, 0.123 g) in 12 mL of H₂O was prepared. 2 drops of concentrated HNO₃ was added and after 30 min stirring, it was added into sealed 25 mL Teflon-lined reactor. After heating at 180°C for 72 h, its temperature cooled down to room temperature at a rate of 5°C/h. A brown block crystalline material 1 was obtained (51% yield based on its cadmium content). Anal. Calcd (%) for 1, C, 64.28; H, 4.05; N, 4.65. Found C, 64.43; H, 4.02; N, 4.65.

2.3 X-ray Crystallography

The single-crystal X-ray pattern of 1 was achieved on a Bruker SMART APEX diffractometer (graphite monochromated MoΚα source, λ: 0.71073 Å) at a ω-scan approach. A direct method was used to solve the structure of 1 (SHLEXS-2014), and a full-matrix least-square F²-based procedure was used to refine the structure (Shelxl-2014) [18]. A geometrical generation approach was used for all hydrogen atoms which were refined isotropically by the riding model. In contrast, the anisotropic displacement parameters were used to refine non-hydrogen atoms. Tables S1 and S2 contain the crystallographic details and selected geometrical variables for 1, respectively. CCDC numbers: 2168412.

2.4 Sensing Experiments

The luminescence sensing characteristics of 1 were evaluated toward some antibiotics including, tinidazole (DTZ), thiamphenicol (THI), secnidazole (SIZ), tinidazole (TDZ), metronidazole (MDZ), ornidazole (ODZ), nitrofurazone (NFZ), chloramphenicol (CAP), sulfamethoxazole (SMT), tetracycline (TCY) and sulfamethazine (SMZ). For this goal, several 1 mg/mL 1 dispersions of (5 mg 1 powder in 5 mL water) were prepared and titrated with 1000 ppm aqueous antibiotics solutions. The averaged quenching efficiency was obtained by the [(I_o-I)/I_o] × 100% formula based on triplicate measurements. In this formula, the fluorescence intensity of 1 before and after the addition of analytes is represented by I_o and I. Additionally, competitive experiments were done by the addition of 2.5 mL SMZ aqueous solution to 2.5 mL of each antibiotic aqueous solution.

2.5 Computational details

The theoretical calculations were used to explain the sensing mechanism of the antibiotics mentioned above. A small unit of 1 comprising of a Cd(II), a bib, an aqua, and three L²⁻ ligands was geometrically optimized. Further, this geometry optimization was also done toward the antibiotics mentioned above. Except for Cd(II), the optimization procedure was performed using B3LYP functional [19a, 19b] using a 6-31G** basis set. A CEP-121G basis set was used toward Cd(II) optimization. A Gaussian 09 program was used for all calculations [19c].

3.1 Structure description of [Cd₂(L)₂(bib)(H₂O)₂] (1)

An asymmetric unit of 1 was proven via the single-crystal analysis of the sample, constituting one Cd(II), a completely deprotonated L²⁻ as the linker, half bib ligand, and one coordinated water molecule (Fig. 1a). The Cd(II) center cation in 1 with a coordination number of 7 has coordinated with two N atom donors in two bib [Cd1–N1 = 2.247(2) Å] and five O atom donors in two different L²⁻ linker [Cd1–O1 = 2.5223(19), Cd1–O2 = 2.304(2), Cd1–O1 = 2.5090(18), Cd1–O6 = 2.328(2) and Cd1–O5 = 2.460(2)Å] and one O atom donor in the coordinated water. In this structure, two imidazole arms have a dihedral angle of 13.05°, while its value with a benzene core is 16.28°. The two carboxylate groups of L²⁻ linker adopt µ₁–η¹:η¹ and µ₂–η²:η¹ coordination modes. The L²⁻ linker has cis-conformation and generates a “V”-type building block (Fig. 1b). Two benzene cores construct a dihedral angle of 8.15°. One 1D loop involving the polymeric ribbons running along “a” direction by the “V”-type L²⁻ linker was formed via the Cd(II) joining (Fig. 1b). The Cd(II)…Cd(II) separation through the “V”-type L²⁻ linker is ca. 12.32 Å. The adjacent 1D polymeric ribbon motifs in the crystal packing diagram (for 1) are strongly bonded via the intermolecular hydrogen bonds, resulting in the formation of a 2D supramolecular layer (Fig. 1c). The π-π interactions of the benzene ring resulted in the formation of a detailed 3D supramolecular motif (with centroid–centroid distance of 3.58Å) of two different “V”-type L²⁻ linkers (Fig. 1d). Also, the lattice water is fixed in the C–H⋯O channels (C3⋯O5: 2.29Å; C13⋯O4: 2.35Å and C15⋯O3: 2.50 Å) as well as the O–H⋯O channels (O7–H7A⋯O2: 2.13 Å; O7–H7B⋯O6: 2.09 Å) created via the hydrogen bonding interactions (Fig. 1e). Also, the critical role of the hydrogen-bonding interactions to form and stabilize the 3D supramolecular architecture has been confirmed [20]. In addition, the bib linkers stretch across the loop, generating a new polyrotaxane-like structure (Fig. 1f).

2.2 PXRD and Thermal studies

The bulk phase purity of 1 was also evaluated by the PXRD, confirming a good match of the experimental PXRD pattern with the simulated pattern. This suggested that both bulk material and single-crystal crystallize in the matching phase (Fig. 3d). The thermogravimetric analysis for 1 involves the separate thermal effect in the temperature range of 37–256 ^oC, corresponding to the removed coordinated water (exptl, 2.9%; calcd, 2.6%) (Fig. S1). Thereafter, further heating led to the decomposition of the framework.

2.3 Luminescent sensing

The photoluminescence (PL) spectra of 1 and H₂L ligand were obtained at ambient conditions. In H₂L, the appearance of the emission band was observed at 356 nm (λ_ex = 285 nm), relating to the n–π* and π–π* transitions [21]. Likewise, a similar broad emission band centered at 360 nm was also obtained for 1 (λ_ex = 285 nm) (Fig. S2). After assessing the photoluminescence properties of 1, its sensing properties were obtained towards antibiotics (vide supra). SMZ drastically decreased the emission intensity of 1, while this diminishing effect is much less in the presence of other antibiotics (Fig. 2a and Fig. S3). Hence, the sensing/probing ability of 1 against SMZ was investigated via the fluorescence titration in detail (Scheme S1), which confirmed that the SMZ addition in the range of 0-600 ppm completely quenches the emission of 1 (Fig. 2b). In this concentration range, a good linear relationship was observed with a K_SV value of 2.98 ×10³ M^− 1 and the limit of detection (LOD) of 1.05 ppm (Fig. 2c). Further, the high selectivity of 1 towards SMZ by 1 was confirmed by its significant quenching effect in the presence of other antibiotics (Fig. 2d).

However, a comparable LOD value was obtained for SMZ concerning the values previously reported for other materials [22]. Feizollahi et al. reported Cu–Ag/GO/GCE sensors, which offered a well-defined signal for SMZ with a LOD of 0.46 ppm. While Jin and his coworker prepared a Tb-based MOF, that detects SMZ with a LOD of 1.58 ppm [22b]. A new UCNPs@MIP was also reported that had good binding capacity, rapid response, critical selectivity as well as good specificity for SMZ with LOD 0.34 ppm [1b]. It is worthy to mention here that, although the antibiotic-sensing performances of the materials mentioned above were evaluated, no investigation into their water stabilities was done. However, high water stability for 1 can be confirmed here, because all experiments were carried out in the aqueous phase. This stability was further complemented with the well-matched PXRD pattern for 1/ SMZ that agrees well with the PXRD pattern of the fresh sample of 1 (Fig. 3b). This indicated that no change in the structure of 1 was observed during sensing experiments and 1 maintained its structural integrity during the experiments.

Also, the recyclability of sensors to detect antibiotics is one very important parameter for their real-world application. Hence, the reusing of 1 after the detection process was done by its separation via the centrifugation of the reaction mixture (10000 rpm for 5 min). It was then ethanol washed 3 times and use in the next sensing run. The results confirmed that the sensing ability of the recovered 1 for the selectively SMZ detection is excellent for at least four recycling runs (Fig. 3a).

Figure 4 shows the results obtained in the XPS for 1 to evaluate its possible weak interactions with SMZ. Comparison of XPS before and after sensing revealed that the framework is stable (Fig. 4a). After SMZ sensing, the binding energies of N1s and O1s of 1 increase from 404.58 eV to 404.84 eV and from 530.78 eV to 531.30 eV, respectively. This indicated some interactions operated between 1 and SMZ during sensing experiments.

The sensing mechanisms confirmed the various reasons for sensing any analyte by a CP. One important reason is an overlap of the analyte electronic absorption band with the CP emission band. This transfers the CP resonance energy to the analyte. In the presented study, a maximum emission quenching of 1 was reached because of the complete overlap of the SMZ absorption band with the 1 emission spectrum (Fig. S4) [23–25].

Table 1

The HOMO-LUMO energies (in eV) for 1 and antibiotics.
Compound	HOMO	LUMO
1	-6.18	-0.74
Thiamphenicol (THI)	-7.09	-1.52
Secnidazole (SIZ)	-6.95	-2.33
Tinidazole (TDZ)	-6.86	-2.36
Dinitrazole (DTZ)	-6.93	-2.27
Metronidazole (MDZ)	-6.96	-2.35
Ornidazole (ODZ)	-7.17	-2.59
Nitrofurazone (NZF)	-6.49	-2.74
Chloramphenical (CAP)	-7.35	-2.46
Sulfamethoxazole (SMT)	-6.23	-0.82
Sulfamethazine (SMZ)	-5.92	-0.92

The density functional theory (DFT) was used to calculate the energies of the HOMO–LUMO of the antibiotics used and 1 for illustrating their decreased effect in the emission intensity of 1 (Table 1, Fig. 5). The most probable reason for this decreased effect is the charge transfer from the excited 1 to the antibiotics’ LUMO. But, this can be achieved for a higher LUMO of 1 than the analytes’ LUMOs. As shown in Table 1, all the antibiotics have lower LUMO energy than 1, confirming the suitable energy positions of the antibiotics to accept the transferred charges from photo-excited 1. This charge transfer phenomenon leads to the relief in PL intensity of 1 [3b]. Despite other antibiotics, the LUMO difference between the 1 and SMT and SMZ is critically low (Fig. 5). Thus, a relatively better position is present in these sulfa drugs for accepting the transferred photo-excited charge from 1. Based on the results, a critically different quenching effect towards 1 was observed in presence of SMT and SMZ, confirming that the charge transfer process may not be the sole reason for the decreased PL intensity. Thus, besides electron/energy transfer, the probable weak interactions between 1 and SMT/SMZ may be another phenomenon responsible for the declined PL intensity. Apart from this, the competitive light absorption may be the other cause of a decline in emission intensity of 1, especially in the presence of SMZ.

Based on the literature [21b], interactions of 1 and antibiotics were evaluated by the construction of the molecular Hirshfeld surfaces in the crystal structure of 1 (Fig. 6). The MOF-d_norm plot (between − 0.5 to 1.5 Å) shows the deep red circular depressions, proving that strong interactions are present (Fig. 6a) [26]. Further, a small relatively shaded area on d_norm surface confirms the presence of the longer and slightly weaker interactions. The total and the decomposed fingerprint plots for 1 in Fig. 6b and 4c) show the presence of the opposite regions where one MOF moiety is a donor center (d_e>d_i) and another moiety is an acceptor center (d_e<d_i). Also, the characteristic fingerprint plots can show the specific atom pairs with close contacts to investigate the share of various solid states' weak interactions. In 1, the O∙∙∙H/H∙∙∙O interactions reveal individual edges in the corresponding 2D fingerprint plots in the region of 0.6 Å < (d_e + d_i) < 2.2 Å as the light sky-blue pattern in full fingerprint 2D plots with 17.0% sharing. Similarly, such individual edges can be observed for the N∙∙∙H/H∙∙∙N interactions in the region of 1.4 Å < (d_e + d_i) < 2.5 Å as a light sky-blue pattern with 1.5% sharing. This proves a facile luminescence quenching phenomenon via the 1 charge transfer by some extensive weak interactions with the antibiotics investigated.

The Crystal Explorer was also used to calculate the crystal lattice void space for 1 [21b] with the standard void cluster parameter “unit cell + 5.0 Å” [22] (Fig. 6d). For this goal, pro-molecule surfaces capped within the unit cell consisting of all atoms of the molecule were generated within a crystal radius of 5.0 Å. The results showed the lattice void volume of 189.16 Å³ for 1 with a void area of 482.19 Å² with globular indices and asphericity of 0.330 and 0.029 units, respectively. These confirm an efficient interaction of the antibiotics with the CP, resulting in an efficient charge/energy transfer from its photo-excited state to the antibiotics' LUMO position relating to the apt energy separation between both antibiotics and MOF. Also, deep red circular depressions over the MOF were proven from the d_norm (Fig. 6a). This is evidence of the strong MOF-antibiotic interactions, which are responsible for the sensing of the analytes by an efficient electron/energy transfer.

A novel 3D supramolecular Cd(II)-based coordinated polymer was synthesized using 4,4’-(1,2-phenlenebis(methyleneoxy))dibenzoic acid and 1,4- bis(1-imidazoly)benzene) containing a one-dimensional (1D) chain with poly-rotaxane, which is woven to produce a 3D supramolecular architecture held by hydrogen-bonded and packing intermolecular interactions between adjacent motifs. This novel MOF design acted as a highly sensitive fluorescent sensor for detecting a well-known sulfa drug, antibiotic sulfamethazine (SMZ). The diminished MOF fluorescence intensity relates to the electron/energy transfer, the weak MOF-antibiotics interactions as well as competitive light absorption. Such investigation is of interest for the inorganic chemists to develop/introduce similar CPs with typical topological characteristics for the sensitive and selective sensing of antibiotics.

Conflicts of interest

There are no conflicts to declare.

Acknowledgments

Initiation Funds for High-level Talents Program of Xi’an International University (grant no.XAIU202104), Shaanxi Association of Higher Education 2021 Higher Education Scientific Research Project (XGH21269) and Shaanxi provincial Education Science"fourteenth five" Schedule 2021 Project (SGH21Y0312)

Declaration of interests

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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Fabrication of a 3D supramolecular Cd(II)-coordination polymer as a luminescent sensor for detection of sulfamethazine

Status:

Version 1

Abstract

Figures

RESEARCH HIGHLIGHTS

1. Introduction

2. Experimental

2.1 Materials and Method

2.2 Synthesis of [Cd₂(L)₂(bib)(H₂O)₂] (1)

2.3 X-ray Crystallography

2.4 Sensing Experiments

2.5 Computational details

3. Results And Discussion

3.1 Structure description of [Cd₂(L)₂(bib)(H₂O)₂] (1)

2.2 PXRD and Thermal studies

2.3 Luminescent sensing

4. Conclusions

Declarations

References

Tables S1 And S2

Supplementary Files

Status:

Version 1

Fabrication of a 3D supramolecular Cd(II)-coordination polymer as a luminescent sensor for detection of sulfamethazine

Status:

Version 1

Abstract

Figures

RESEARCH HIGHLIGHTS

1. Introduction

2. Experimental

2.1 Materials and Method

2.2 Synthesis of [Cd2(L)2(bib)(H2O)2] (1)

2.3 X-ray Crystallography

2.4 Sensing Experiments

2.5 Computational details

3. Results And Discussion

3.1 Structure description of [Cd2(L)2(bib)(H2O)2] (1)

2.2 PXRD and Thermal studies

2.3 Luminescent sensing

4. Conclusions

Declarations

References

Tables S1 And S2

Supplementary Files

Status:

Version 1

2.2 Synthesis of [Cd₂(L)₂(bib)(H₂O)₂] (1)

3.1 Structure description of [Cd₂(L)₂(bib)(H₂O)₂] (1)