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One-step assembly of Pd-Keggin-polyoxometalates for catalytic benzothiadiazole generation and derived cell-imaging probe application
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Xianqiang Huanga, *, Weilong Cuib, Sen Liua, Gang Liua, Yalin Zhanga, Zhihao Zhangb, Guodong Shena, Zhen Lia, Jianyong Wangb, *, Yifa Chenc, d, *
Chinese Chemical Letters | 2023, 34(6) : 107692
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Chinese Chemical Letters | 2023, 34(6): 107692
• Communication •
One-step assembly of Pd-Keggin-polyoxometalates for catalytic benzothiadiazole generation and derived cell-imaging probe application
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Xianqiang Huanga, *, Weilong Cuib, Sen Liua, Gang Liua, Yalin Zhanga, Zhihao Zhangb, Guodong Shena, Zhen Lia, Jianyong Wangb, *, Yifa Chenc, d, *
Affiliations
  • a Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry & Chemical Engineering, Liaocheng University, Liaocheng 252059, China
  • b Key Laboratory of Biobased Material and Green Papermaking, Key Laboratory of Pulp & Paper Science and Technology of Shandong Province/Ministry of Education, Qilu University of Technology (Shandong Academy of Sciences), Ji'nan 250353, China
  • c National and Local Joint Engineering Research Center of MPTES in High Energy and Safety LIBs, Engineering Research Center of MTEES (Ministry of Education), Key Lab. of ETESPG(GHEI), South China Normal University, Guangzhou 510006, China
  • d Jiangsu Collaborative Innovation Centre of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China
Published: 2023-06-15 doi: 10.1016/j.cclet.2022.07.035
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One-step assembly of organic-ligand modified Pd-Keggin-POMs has been rarely reported, so as for their applications in catalytic benzothiadiazole generation and derived cell-imaging probing. Herein, three Pd-Keggin-POMs (compounds 1–3) have been successfully synthesized via a one-step assembly strategy. Thus-obtained Pd-Keggin-POMs with well-defined structures and heterogeneous properties enable highly efficient catalytic benzothiadiazole generation. Specifically, compound 3 showed outstanding catalytic activities in Suzuki-Miyaura coupling reactions for the generation of benzothiadiazole derivatives (yields, 90%-97%) and was represented as one of the best catalysts reported to date. Consequently, the obtained benzothiadiazoles were used as the bio-probe for tracking lipid droplets in living-cells and exhibited large Stokes shifts (130 nm), low cytotoxicity and good targeting, which could be also applied to mark the distribution of LDs in living HeLa cells. Systematic investigations clearly decipher the functions of Pd-Keggin-POMs toward finding novel bio-probe materials, highlighting a new insight into the generation of sustainable materials in life-science.

Metal-organic-pallidum-POMs  /  Crystal structure  /  Suzuki-Miyaura  /  Fluorescent probe  /  LDs
Xianqiang Huang, Weilong Cui, Sen Liu, Gang Liu, Yalin Zhang, Zhihao Zhang, Guodong Shen, Zhen Li, Jianyong Wang, Yifa Chen. One-step assembly of Pd-Keggin-polyoxometalates for catalytic benzothiadiazole generation and derived cell-imaging probe application[J]. Chinese Chemical Letters, 2023 , 34 (6) : 107692 - . DOI: 10.1016/j.cclet.2022.07.035
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2,1,3-Benzothiadiazole is a kind of essential structural motif in the fabrication of luminescent, electronic and biological derivatives [1-4], in which they have intriguing optical properties owing to their strong electron-withdrawing capacity, strong light absorption efficiency and tailorable band potentials, etc. [5-7]. The as-generated multifunctional materials have attracted considerable attention in the field of biological imaging [8], organic light emitting diodes [9], sensitizers for dye-sensitized solar cells (DSC) [10], two-photon absorption (2PA) chromophores [11] and organic photovoltaic cells [12]. Traditionally, 2,1,3-benzothiadiazole derivatives have been successively synthesized in the presence of Pd(dppf)Cl2, Pd(PPh)4 or prepared Pd-complexes [13-16]. However, the recycling utilization of these noble metal catalysts remains a challenge due to the homogenous nature, thus these synthesis processes are generally expensive and unmet for the criteria of sustainable chemistry. Therefore, it is of paramount importance to explore efficient heterogeneous catalysts that enable the sustainably catalytic generation of functionalized 2,1,3-benzothiadiazole derivatives.
Polyoxometalates (POMs), as a family of metal oxide clusters incorporating early transition metals, have emerged as a brand-new platform materials and undergone explosive growth for many suitable applications including catalysis [17-23], magnetism [24,25], energy [26] and materials science [27-29], etc. Generally, the combination of reactive transition metal-complexes units into POM anions with favourable catalytic properties has received considerable interest in the catalytic reactions [30-32]. Specifically, the assembly of POMs with Pd cations produces a family of binary Pd-POMs, which not only possess the diverse structures, but also have significant catalytic applications in construction of C-C bonds owing to the catalytic properties of Pd [33]. However, so far, only a few organic ligand-modified Pd-POMs have been synthesized and efforts to extend this research realm of Pd-POMs have been of limited success. In the early work, Mizuno's group proposed two Pd-POMs [(en)Pd(4,4′-bpy)]2[α-SiW12O40]·8DMSO·4DMF and [(en)Pd(OH2)2]2 [α-SiW12O40] with structurally well-defined clusters [34]. Later, Neumann revealed the synthetic strategy of PdII(15-crown-5-phen)Cl2-H5PV2Mo10O40 (phen = 1,10-phenanthroline) with high catalytic activity in the Wacker oxidation [35]. Besides, Sun's group synthesized a binary POMs@Pd-cage complex with excellent desulfurization properties [36]. Additionally, Kortz's group reported that the successful introduction of Pd metals in POMs skeleton could not only develop the precise local structure determination but also explore the integration of intrinsic catalytic properties [37-39]. In these cases, the aforementioned synthetic strategy of Pd-POMs usually requires the pre-synthesis or modification of specially designed organic ligands, which makes the preparation process complicated, expensive and time-consuming [40]. As far as we know, the one-pot syntheses of organic ligand modified Pd-POMs with defined structures have been rarely reported, which encourages us with great interest in developing powerful strategy to meet the requirements. Hence, the exploration of novel one-pot synthetic strategy for the preparation of Pd-POMs that can be applicable in the catalytic production of 2,1,3-benzothiadiazole derivatives is highly desirable yet largely unmet.
In this work, we firstly adopted the readily available liquid imidazoles as N-ligands and three imidazole-based Pd-POMs, [Pd(1-eIM)4]HPW12O40·DMSO (1), [Pd(1-pIM)4]2PMo11VO40 (2) and [Pd(1-mIM)4]2HPMo10V2O40·4DMSO (3) were successfully obtained through a facile one-step reaction and fully characterized by single crystal X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FT-IR) and elemental analysis (EA), etc. The above strategy is considerably simple and straightforward in the synthesis of binary Pd-POMs, owing to the complicated synthesis or modification procedures of organic ligands can be omitted. Interestingly, compound 3 exhibited extraordinary catalytic performance in the construction of 2,1,3-benzothiadiazole derivatives under mild conditions without any additional co-catalysts. Furthermore, these Pd-POMs can be fully recycled and reused with maintained catalytic activities. Moreover, in parallel to our research on the catalytic synthesis of 2,1,3-benzothiadiazole derivatives, a novel bio-probe NBDS-N has been designed with effective D-π-A structure and minimal biotoxicity, which exhibited sufficiently sensitive properties to lipid droplets (Fig. 1). The work paves a new way to design efficient POMs based catalysts for life science applications.
In this work, compounds 1–3 were synthesized by the reaction of Pd(OAc)2, Keggin POMs and imidazole derivatives in the absence or presence of CF3COOH. The synthetic pathway of binary Pd-POMs is elaborated in Fig. 2: Firstly, reacting N-donor imidazole ligands with Pd(OAc)2 to substitute the acetate and give Pd-imidazole complexes in the DMSO, and then followed by the method of ion exchange reaction between Pd-imidazole complexes and three Keggin-type POMs in DMSO to yield three Pd-POMs 1–3 (Fig. 2). In the reaction, the reaction environment caused by inherent basic of different imidazoles were slightly different, and the solubility of three Pd-POMs was also different in DMSO solution. To obtain the crystals of compounds 2 and 3, different amounts of CF3COOH were added into the reaction to increase the solubility of Pd-POMs in DMSO and the amounts of CF3COOH in the syntheses of compounds 2 and 3 were 30 µL and 70 µL, respectively.
SXRD shows that compound 1 crystallizes in the monoclinic space groups P21/n and is composed of one α-Keggin-type [PW12O40]3- polyanion and one (Pd(1-eIM)4)2+ cations (Fig. 2). In (Pd(1-eIM)4)2+ cations, the four 1-eIM nitrogens [N(2), N(2A), N(4) and N(6)] respectively coordinate to Pd(1) with Pd-N distances of 1.96(2)- 2.00(2) Å and form nearly square-planar coordination geometry. The distance of Pd-N bonds is close to those found in Pd(F6acac)2(4-ClC5H4N)4 (2.019(5)−2.034(5) Å) [41]. The Keggin [PW12O40]3− polyanion has an approximate Td symmetry based on a central PO4 tetrahedron surrounded by 12 WO6 octahedra arranged in four groups of three edge-shaped octahedra, W3O13 [42].
When [PW12O40]3− was replaced by [PMo11VO40]4− and [PMo10V2O40]5−, compounds 2 and 3 are achieved, respectively (Fig. 2). Compounds 2 and 3 are isostructural, thus the structure of compound 3 is described here as an example. Compound 3 crystallizes in the Triclinic space groups P-1 and consisted of two Pd2+ cations and one Keggin PMo10V2O405− polyoxoanion. The P-O and Mo-O lengths are in the range of 1.455(19)−1.58(19) Å, and 1.635(11)−2.504(19) Å, respectively [43,44]. In compound 3, each Pd center also displays a four-coordinated geometry and is completed by four imidazole donors. The corresponding bond lengths and angles of compound 3 are given in Table S1 (Supporting information). The Pd-N bond lengths (2.000(10)−2.019(11) Å, Table S2 in Supporting information) are close to those found in compound 1 and the reported Pd24L24 (2.02–2.03 Å; L = tris(4-(pyrimidin-5-yl)phenyl)amine) [45]. Although compounds 2 and 3 were prepared similarly to 1, the structures of them were still obviously differed from that of 1 (Fig. 2). The structural difference reveals that polyanion plays a crucial role in the assembly of Pd-Keggin POMs.
Given the fact that the 2,1,3-benzothiadiazole derivatives were one of the key organic functionalized materials and the Pd-POMs encompassed potential catalytic centers in the formation of these functionalized molecules [46-48], we decided to evaluate the catalytic activities of these Pd-POMs in Suzuki-Miyaura coupling reactions (Scheme 1). Our catalytic experiment was initially performed on the coupling reaction of 4,7-dibromobenzo[2,1,3]thiadiazole 5a and phenylboronic acid 6a as a model substrate with the conditions of 0.5 mol% catalysts, 5a (0.25 mmol), phenylboronic acid 6a (0.55 mmol), and K2CO3 (0.75 mmol) in 4 mL solvent at 60 ℃ for 2 h and the optimum reaction results were listed in Fig. 3. Preliminary screenings indicated that employing H3PW12O40, H4PMo11VO40 and H5PMo10V2O40 as the catalysts at 60 ℃ afforded a trace amount of the desired product as well as the result of no catalyst. Then, we investigated the palladium catalyst in terms of this transformation and the desired product 7a was achieved in 17% yield. Replacement of Pd(OAc)2 with the mixture of Pd(OAc)2 and H5PMo10V2O40 gave the desired product in 40% yield. Interestingly, when compounds 1–3 were applied as the catalysts, the yields of product 7a were dramatically increased, indicating the intramolecular cooperation between cation and anion in compounds 1-3 might play vital role in the catalytic process. Specifically, an excellent yield of 93% was obtained using the compound 3 as the catalyst (Fig. 3a). This preliminary result implied that the combination of Pd complexes and Keggin-POMs H5PMo10V2O40, i.e., compound 3, can dramatically enhance the catalytic activities of cross-coupling reactions of aryl dibromides with phenylboronic acid owing to the stronger oxidation properties of H5PMo10V2O40. Additionally, the effect of reaction time on the Suzuki-Miyaura coupling were also monitored at different time intervals and found that model reaction of 5a and 6a gave the corresponding coupling product in 93% yield in 120 min (Fig. 3b). Besides, attempts to increase or lower the reaction temperature led to the decrease of reaction efficiency (Fig. 3c). Further investigation on the reaction solvents showed that EtOH-H2O (3:1) was the optimal solvent for this transformation (Fig. 3d). Thus, the optimal reaction conditions were eventually determined to include 5a (0.25 mmol) and 6a (0.55 mmol) in EtOH-H2O (3:1) at 60 ℃ for 2 h in the presence of compound 3 (0.5 mol%) and it could achieve a 93% yield in the formation of product 7a.
With the optimal conditions, we explored the substrate scope of this Suzuki-Miyaura coupling reaction. As shown in Table 1, a series of phenylboronic acid derivatives, regardless of electron-donating or -withdrawing group on the phenyl ring, could efficiently induce the coupling reaction to produce the desired products in excellent yields, and compound 3 also afforded the corresponding biaryl products in excellent yields (90%−97%) (Table 1, entries 1–7). In addition, sterically hindered meta-methylphenylboronic acid or meta-chrolophenylboronic acid gives a relatively lower yield compared to its para-counterparts (Table 1, entries 6 and 7). Furthermore, the reaction of 4-bromo-7-nitro-2,1,3-benzothiadiazole and arylboronic acid underwent cross-coupling smoothly and afforded the desired products in 94%−97% yields (Table 1, 7h-7j). Noteworthy, compound 3 as heterogeneous catalyst displays superior performance to the previous homogeneous and heterogeneous catalysts (e.g., nano-sized Pd6L8 (L = 1,3,5-tris(4′-pyridyloxadiazole)−2,4,6-triethylbenzene) [49], guar gum supported Pd catalyst [50], etc.) reported to date.
To determine the heterogeneous nature of Pd-POMs clusters in the coupling reaction between 4,7-dibromobenzo[c][2,1,3]thia-diazole and PhB(OH)2, the leaching experiment was investigated. The solid catalyst 3 was filtrated from the reaction after 1 h under the optimum conditions and the filtrate was subsequently reacted at 60 ℃ for additional 1 h, no yield change of 7a was detected, indicating the reaction was indeed a heterogeneous catalytic process (Fig. 3b). In addition, atomic absorption analysis showed that there were no palladium, vanadium and molybdenum ions in the filtrate of the reaction system, which further proved that the catalytic system using 3 was heterogeneous in the coupling reactions. Next, the reusability of the hybrid catalyst was also evaluated in the coupling of 4,7-dibromobenzo[c][2,1,3]thiadiazole and phenylboronic acid. After the reaction, the catalyst 3 was separated by centrifugation, washed with ethyl acetate three times, and then subjected to the second run under the same conditions. The catalyst 3 could be recycled and reused for three times with remained catalytic activity [yields of 7a: 93% (first run), 92% (second run), 92% (third run)] (Fig. 4a). In addition, there were almost no changes detected in the XPS, FT-IR and PXRD tests of the recycled compound 3 (Figs. 4b-d).
Lipid droplets are an important dynamic subcellular organelle in the cell for storing intracellular lipids, and lipid homeostasis has important implications for cellular physiology and pathophysiology [51,52]. It has been demonstrated that lipid droplets are able to participate in the transport of a wide range of enzymes and proteins and thus in the dynamic physiological homeostasis of the cell [53,54]. Abnormalities in intracellular lipid droplet levels may lead to disturbances in the cellular physiological environment and thus induce the development of related diseases, such as cardiovascular disease, cancer [55,56]. Therefore, achieving intracellular tracking and imaging of LDs is important for monitoring the normal physiological environment within cells.
In addition to the above research work, an organic bio-probe NBDS-N (FF) for tracking and intracellular imaging of lipid droplets was also designed and synthesized, which was consisted of a triphenylamine chain segment as an electron donor group and a benzothiadiazole main body as an electron acceptor group, forming a typical D-π-A molecular structure. Immediately afterwards, the spectral properties of the probe NBDS-N were studied. Firstly, the absorption and emission spectra of the probe NBDS-N in different solvents including hexane, toluene, dichloromethane, tetrahydrofuran (THF), ethanol (EtOH), acetone, acetonitrile, N, N-dimethylformamide (DMF), methanol (MeOH), ethylene glycol, dimethyl sulfoxide (DMSO) were investigated. As shown in Fig. 5a, for the probe NBDS-N, the results demonstrated that the absorption spectra of probe NBDS-N exhibited a small shift in organic solvents around at 450 nm with almost same absorption intensity. The emission spectra of probe NBDS-N showed an increasing fluorescence intensity in liposoluble solvents especially in hexane, toluene and THF. The results indicated that probe NBDS-N could be applied for monitoring LDs in living cells (Fig. 5b). Secondly, we investigated the optical properties of the probe NBDS-N in MeOH with different concentrations of ethyl acetate. As shown in Fig. 5c, the result showed that when the ethyl acetate content enhanced in the mixed solution system, the fluorescence intensity increased considerably and accompanied by a slight blue shift from 620 nm to 605 nm with a large Stokes shift (130 nm). These apparent fluorescence intensity change indicated that the probe NBDS-N possessed a significant detection effect on LDs.
According to the significant variation in fluorescence intensity exhibited by probe NBDS-N in different viscous and polar solvents, the cellular biotoxicity of the probe NBDS-N was verified by MTT assay (Fig. 5d). It was shown that the cell viability of the probe NBDS-N could still reach more than 90% after co-incubation with HeLa cells for 24 h. This data indicated that the probe could be used as a practical tool for marking LDs under complex biological environments with low biotoxicity. Subsequently, the co-localization fluorescence imaging of the probe NBDS-N was accomplished in living HeLa cells due to the different emission wavelengths of the probe NBDS-N and the commercial organic dye Nile Red. We found that green fluorescence imaging was conducted by probe NBDS-N (Fig. 6). Nile red was also applied to incubate the same cells, which exhibited red fluorescence imaging as depicted in Fig. 6c. The merge image was also shown in Fig. 6d. Moreover, the parameters of co-localization image were obviously depicted in Fig. 6e, indicating that the red and green channel was overlapped largely with Pearson correlation coefficient up to 0.91. The above results suggested that this novel probe NBDS-N could be used for LDs marker in living bio-samples.
In summary, a series of imidazole modified binary Pd-POMs with defined structures have been prepared through a facile and rarely reported one-step approach and successfully applied to synthesize 2,1,3-benzothiadiazoles by Suzuki-Miyaura coupling reaction. Specifically, compound 3 exhibits outstanding heterogeneous catalytic performance for Suzuki-Miyaura coupling reaction of aryl dibromides (excellent yields up to 97%) and it can be reused with remained high activity and durability. Subsequently, a novel organic bio-probe NBDS-N was constructed for LDs cell imaging by using a benzothiadiazole derivative as the main body and it exhibited good properties including large Stokes shift (130 nm), good LDs distribution, and a low biological toxicity. Furthermore, bio-probe NBDS-N successfully labelled the distribution of LDs in living HeLa cells. The work might shed light on the design of efficient POMs based catalysts for the derived potential applications in life science.
Declaration of competing interest
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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.
Acknowledgments
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Acknowledgments should be inserted at the end of the paper, before the references, not as a footnote to the title. This work was financially supported by National Natural Science Foundation of China (Nos. 21871125, 22171139, 21801145 and 21901122), the Natural Science Foundation of Shandong Province, China (Nos. ZR2019MB043 and ZR2019QB022), Shandong Provincial Key R & D Program/Major Science and Technology Innovation Project of Shandong Province (No. 2019JZZY020230) and the Construction Project of Quality Curriculum for Postgraduate Education of Shandong Province (No. SDYKC19057).
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Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.cclet.2022.07.035.
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Year 2023 volume 34 Issue 6
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doi: 10.1016/j.cclet.2022.07.035
  • Receive Date：2022-05-02
  • Online Date：2025-11-21
  • Published：2023-06-15
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  • Received：2022-05-02
  • Revised：2022-06-01
  • Accepted：2022-07-17
Affiliations
    a Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry & Chemical Engineering, Liaocheng University, Liaocheng 252059, China
    b Key Laboratory of Biobased Material and Green Papermaking, Key Laboratory of Pulp & Paper Science and Technology of Shandong Province/Ministry of Education, Qilu University of Technology (Shandong Academy of Sciences), Ji'nan 250353, China
    c National and Local Joint Engineering Research Center of MPTES in High Energy and Safety LIBs, Engineering Research Center of MTEES (Ministry of Education), Key Lab. of ETESPG(GHEI), South China Normal University, Guangzhou 510006, China
    d Jiangsu Collaborative Innovation Centre of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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