Current advances in UV-based advanced oxidation processes for the abatement of fluoroquinolone antibiotics in wastewater

Quinoxalin-2(1H)-one, as a significant heterocyclic unit, has been found important applications in synthetic chemistry, materials, natural products and pharmaceuticals because of their innate outstanding biological activities and excellent chemical characters [1], and their biological activities can be significantly influenced if the substituents is introduced into the N1- and C3-positions of the quinoxalin-2(1H)-one [2]. In particular, 3-substituted quinoxalin-2(1H)-ones have been developed into powerful drugs due to their strong pharmacological effects [3], such as ataquimast, antinicrobial, anticancer, Fxa coagulation inhibitors and glycogen phosphorylase inhibitor (Fig. 1) [4]. Therefore, a number of methods have been developed for their synthesis [5]. Generally, they are synthesized by cyclization of derivatives of aniline or 1, 2-diaminobenzene with suitable partners. However, the disadvantages including pre-functionalization of the partners and multi-step synthesis limit its application [6]. In recent years, direct C-H bond functionalization at the C3-position of quinoxalin-2(1H)-one has become a straightforward access to the 3-substituted quinoxalin-2(1H)-one derivatives, and various remarkable work has been achieved [7-12]. For instances, our group in 2019 reported a first example of oxidative C-H fluoroalkoxylation of quinoxalinones with fluoroalkyl alcohols under transition-metal and solvent-free conditions [8b]. This method can also be extended to the facile and efficient synthesis of histamine-4 receptor. The same year, Sun's group presented an efficient electrochemical approach for the C(sp²)–H phosphonation of quinoxalin-2(1H)-ones and C(sp³)–H phosphonation of xanthenes [9a]. More interestingly, the group of Pan disclosed a photocatalyst-free visible-light-promoted sulfenylation of quinoxalinones with thiols via cross-dehydrogenative coupling [10b]. Shortly after this discovery, He's group demonstrated a visible-light-promoted amidation of quinoxalin-2(1H)-ones [11b]. In a very recent contribution, a mild and eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids using ambient air as the sole oxidant at room temperature was also established by the same group [12a]. In sharp contrast, the alkenylation of quinoxalin-2(1H)-ones was rarely reported.

Figure 1

Figure 1.  Examples of quinoxalin-2(1H)-one skeleton-based bioactive molecules.

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Photocatalysis has become a powerful strategy for organic synthesis due to the advantages of low energy consumption and environmental protection [13]. For example, MacMillan et al. in 2016 reported a photocatalyzed C-H arylation of aliphatic amines with aryl bromides, providing a complement to existing cross-coupling technologies [13a]. In 2021, He' group developed the first example of visible-light induced one-pot tandem reaction of arylacrylamides, CHF₂CO₂H and PhI(OAc)₂, affording an eco-friendly and practical method to access various difluoromethylated oxindoles [13b]. The same year, Jin and coworkers developed photocatalyst-free radical tandem cyclization of quinazolinones containing an unactivated alkene moiety with difluoro bromides under illumination, giving a practical method for the synthesis of fluorine-containing ring-fused quinazolinones [13f]. In recent years, with increasing attention to renewable energy, considerable efforts have been switched to the development of photocatalytic reactions that excited by the sunlight, which is known as a renewable and simple accessible light source [14]. Our research interests focus on the development of novel and effective methodologies for the direct modification ofN-containing heterocycles [15], herein, we demonstrated a direct alkenylation reaction between quinoxalin-2(1H)-ones and methyl ketones. Compared with our previous work [15a], this transformation was achieved through a combination of Mannich-type reaction and solar photocatalysis, which could be completed within 15min, providing a green and efficient solution for the synthesis of potentially bioactive compounds that containing a 3, 4-dihydroquinoxalin-2(1H)-one structure (Scheme 1b).

Scheme 1

Scheme 1.  Modification of quinoxalin-2(1H)-ones by C-H functionalization.

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1-Methylquinoxalin-2(1H)-one (1a) and acetone (2a) were chosen as starting materials to screen the reaction conditions. The target product (3a) was obtained in 80% yield when the reaction was performed by using 25mol% of CH₃SO₃H as a catalyst under the irradiation of sunlight for 15min (Table 1, entry 1). Other acid catalyst, such as CF₃COOH and HBF₄ gave the relative lower yield under the same conditions (Table 1, entries 2 and 3). No product was obtained in the absence of any acid catalyst (Table 1, entry 4). When used MeCN or DMF as solvent and 2.0 equiv. of acetone as substrate, 76% or 52% yield was obtained respectively (Table 1, entries 5 and 6). Extended reaction time to 30min did not enhanced product yield (Table 1, entry 7). There was no desired product generated when the reaction was carried out under dark condition (Table 1, entry 8).

Table 1

Table 1.  Screening of reaction conditions.^a

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With the optimum reaction conditions in hands, we then examined the substrate scope of the reaction by employing various quinoxalin-2(1H)-ones (1) with acetone (2a) (Scheme 2). Firstly, the N-substituted groups such as N-methyl, N-ethyl, N-cyclopropylmethyl, N-keto and N-ester were well compatible under the standard conditions, giving the desired products (3a-e) in 72%–80% yields. It is worth mentioning that quinoxalin-2(1H)-one with a sensitive allyl group, which could be further functionalized, also could give the product (3f) in 69% yield. A wide range of quinoxalin-2(1H)-ones with different benzyl groups, bearing both electron-donating and electron-withdrawing substituents at ortho-, meta-, or para-position could undergo the reaction smoothly, affording the corresponding products (3g–n) in 40%–72% yields. Importantly, the N-free quinoxalin-2(1H)-one could undergo the reaction smoothly, providing the product (3o) in 45% yield. Besides, plenty of quinoxalin-2(1H)-ones that bear the functional groups including methyl, halogen, tert-butyl, methoxy or trifluoromethyl at C5-, C6- or C7-position also gave the desired products in satisfactory yield (3p-3w). To expand the substrate scope of N-heterocycles, we also tested quinoline, isoquinoline, quinoxaline, benzimidazole and benzothiazole under standard conditions, however, no corresponding product was obtained (see Supporting information).

Scheme 2

Scheme 2.  Substrate scope of quinoxalin-2(1H)-ones. Reaction conditions: 1 (0.2 mmol), 2a (1.0 mL), CH₃SO₃H (25 mol%), open flask, sunlight, room temperature, 15 min. Isolated yields. ^a Reaction was performed on a 1 mmol scale.

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Subsequently, we evaluated the substrate scope of methyl ketones for the reaction (Scheme 3). To reduce the dosage of reactant, the reactions were performed with 2.0 equiv. of methyl ketones by using acetonitrile as solvent. To our delight, both long-chain and cycloalkyl methyl ketones could undergo the reaction smoothly, giving the corresponding products (3x–3ad) in 58%–79% yields. The molecular structure of 3y was confirmed by X-ray crystallographic analysis (CCDC: 2060383). It was found that the molecular structure was more stable in (Z)-configuration probably because the effect of hydrogen bond interaction between amine and carbonyl group. Then, we found that cyclopentanone skeleton could also react with quinoxalin-2(1H)-one smoothly to deliver the target products (3ae and 3af) in moderate yield. The subsequent exploration found that the aryl methyl ketones, such as acetophenone, 1-(furan-2-yl)ethan-1-one and 1-(thiophen-2-yl)ethan-1-one were also could be converted into target products (3ag-3ai) in acceptable yields. Unfortunately, the substrates like ethyl acetate, acetonitrile, nitromethane, ethyl acetoacetate, and acetylacetone were not compatible under standard conditions (Supporting information).

Scheme 3

Scheme 3.  Substrate scope of methyl ketones. Reaction conditions: 1a (0.2 mmol), 2 (2.0 equiv.), CH₃SO₃H (25 mol%), MeCN (1.0 mL), open flask, sunlight, room temperature, 15min. Isolated yields.

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To show the synthetic utility of this protocol, a gram-scale synthesis experiment was performed to give the target product (3a) in 75% yield (Scheme 4). Interestingly, the anticancer compound (3aj) and antimicrobial compound (3ak) were obtained in moderate yields by using our strategy [16]. Moreover, since the molecules that bearing a 3, 4 dihydroquinoxalin-2(1H)-one framework are a promising class of biologically active compounds, in this regard, several bioactive molecules such as naproxen derivative, frambinone, ibuprofen derivative, vanillylacetone, nabumetone and pregnenolone acetate were selected to react with 1-methylquinoxalin-2(1H)-one directly, providing the potentially active molecules (3al-3aq) in 52%–70% yields.

Scheme 4

Scheme 4.  Gram-scale synthesis and application. Reaction conditions: 1a (0.2mmol), 2 (2.0 equiv.), CH₃SO₃H (25mol%), MeCN (1.0mL), open flask, sunlight, room temperature, 15min. Isolated yields.

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To study the reaction mechanism, a series of control experiments were carried out. Product 4 was generated instead of target product 3a when the reaction was performed under nitrogen atmosphere (Scheme 5). This result showed that oxygen in air was included in the subsequent oxidation process. To confirm the assumption, the oxidation process of compound 4 was studied. First, target product 3 was formed in 0%, 79% and 82% yields when the reaction performed under nitrogen, air or oxygen atmosphere respectively (Scheme 5). Second, the reaction was inhibited when singlet oxygen inhibitor (NaN₃) was involved in the transformation (Scheme 5). Furthermore, compound 4 could not be converted into target product 3 when the reaction was performed in dark condition (Scheme 5). These experimental results strongly supported that the singlet oxygen ¹O₂, which was generated from triplet oxygen ³O₂ through photocatalysis, serves as the real oxidant.

Scheme 5

Scheme 5.  Control experiments.

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On the basis of above results and previous reports [8-12], we proposed a possible mechanism for this reaction (Scheme 6). Firstly, substrate 1a was transformed into intermediate A through a protonation process. Meanwhile, acetone 2a was converted to the enol form B under acidic condition. Then, a Mannich-type reaction took place between intermediates A and B to give the intermediate C, which underwent a deprotonation process to provide the key compound 4. It was found that organic molecules that containing a quinoxalin-2(1H)-one skeleton could act as a photosensitizer to generate ¹O₂ from O₂ under the irradiation of visible light [12p]. In this regard, compounds1a, 4 or 3a was excited by visible light to provide the excited-species 1a^*, 4^* or 3a^*, which acted as a photosensitizer and underwent an energy transfer (ET) process with O₂ to give ¹O₂, along with the regeneration of ground-state compounds 1a, 4 or 3a. Finally, compound 4 underwent the single-electron-transfer (SET) process with ¹O₂ to give the desired product with the generation of H₂O₂, which was detected by H₂O₂ test paper (Supporting information) [12a] [17]. We proposed that the electron-withdrawing effects of carbonyl group that exists in quinoxalin-2(1H)-one skeleton lower down the electron cloud density of the enamine moiety, making it difficult to be oxidized and can survive under this H₂O₂ oxidation conditions.

Scheme 6

Scheme 6.  Plausible mechanism.

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In conclusion, this study described a novel strategy for the olefination of quinoxalin-2(1H)-ones with methyl ketones. Various substrates were compatible under standard condition, providing the corresponding products in moderate to good yields. Control experiments revealed that a Mannich-type reaction and oxidative process were involved in the transformation.

Declaration of competing interest

The authors declare that they have no conflict of interest.

Acknowledgments

We thank the Natural Science Foundation of Zhejiang Province (No. LY21B060009) and the National Natural Science Foundation of China (No. 21871071) for financial support.

Appendix A. Supplementary data

Supplementary material related to this article can befound, in the online version, at doi:https://doi.org/10.1016/j.cclet.2021.04.016.

References

1. [1]

   S. Bhatt, S. Chatterjee, Environ. Pollut. 315 (2022) 120440.
   

2. [2]

   E.Y. Klein, T.P. Van Boeckel, E.M. Martinez, et al., Proc. Natl. Acad. Sci. U. S. A. 115 (2018) E3463–E3470.
   

3. [3]

   D. Schar, E.Y. Klein, R. Laxminarayan, et al., Sci. Rep. 10 (2020) 21878.  doi: 10.1038/s41598-020-78849-3
   

4. [4]

   Q.Q. Zhang, G.G. Ying, C.G. Pan, et al., Environ. Sci. Technol. 49 (2015) 6772–6782.  doi: 10.1021/acs.est.5b00729
   

5. [5]

   I.T. Carvalho, L. Santos, Environ. Int. 94 (2016) 736–757.
   

6. [6]

   X. Van Doorslaer, J. Dewulf, H. Van Langenhove, K. Demeestere, Sci. Total Environ. 500 (2014) 250–269.
   

7. [7]

   M. Zou, W. Tian, J. Zhao, et al., Process Saf. Environ. Prot. 160 (2022) 116–129.  doi: 10.1016/j.psep.2022.02.013
   

8. [8]

   S. Li, W. Shi, W. Liu, et al., Sci. Total Environ. 615 (2018) 906–917.  doi: 10.1016/j.scitotenv.2017.09.328
   

9. [9]

   S. Li, Y. Liu, Y. Wu, et al., Natl. Sci. Open. 1 (2022) 20220029.  doi: 10.1360/nso/20220029
   

10. [10]

    E.M. Golet, A.C. Alder, W. Giger, Environ. Sci. Technol. 36 (2002) 3645–3651.  doi: 10.1021/es0256212
    

11. [11]

    M. Sturini, A. Speltini, F. Maraschi, et al., Chemosphere 134 (2015) 313–318.  doi: 10.1016/j.chemosphere.2015.04.081
    

12. [12]

    Z. Li, J. Wang, J. Chang, et al., Sci. Total Environ. 857 (2023) 159172.  doi: 10.1016/j.scitotenv.2022.159172
    

13. [13]

    R. Anjali, S. Shanthakumar, J. Environ. Manage. 246 (2019) 51–62.  doi: 10.1016/j.jenvman.2019.05.090
    

14. [14]

    Y. Zhang, Y.G. Zhao, F. Maqbool, Y. Hu, J. Water Process. Eng. 45 (2022) 102496.  doi: 10.1016/j.jwpe.2021.102496
    

15. [15]

    Y. Chuang, S. Chen, C. Chinn, W. Mitch, Environ. Sci. Technol. 51 (2017) 13859–13868.  doi: 10.1021/acs.est.7b03570
    

16. [16]

    C. Wang, N. Moore, K. Bircher, et al., Water Res. 161 (2019) 448–458.  doi: 10.1016/j.watres.2019.06.033
    

17. [17]

    J. Rodriguez-Chueca, S. Varella della Giustina, J. Rocha, et al., Sci. Total Environ. 652 (2019) 1051–1061.  doi: 10.1016/j.scitotenv.2018.10.223
    

18. [18]

    J. Rodríguez-Chueca, E. Laski, C. García-Cañibano, et al., Sci. Total Environ. 630 (2018) 1216–1225.  doi: 10.1016/j.scitotenv.2018.02.279
    

19. [19]

    Y. Chen, J. Yang, L. Zeng, M. Zhu, Crit. Rev. Environ. Sci. Technol. 52 (2022) 1401–1448.  doi: 10.1080/10643389.2020.1859289
    

20. [20]

    S. Shurbaji, P.T. Huong, T.M. Altahtamouni, Catalysts 11 (2021) 437.  doi: 10.3390/catal11040437
    

21. [21]

    Y. Gou, P. Chen, L. Yang, et al., Chemosphere 270 (2021) 129481.  doi: 10.1016/j.chemosphere.2020.129481
    

22. [22]

    X. Liu, Y. Zhou, J. Zhang, et al., Chem. Eng. J. 347 (2018) 379–397.  doi: 10.1016/j.cej.2018.04.142
    

23. [23]

    T. Song, G. Li, R. Hu, et al., Catalysts 12 (2022) 1025.  doi: 10.3390/catal12091025
    

24. [24]

    Z. Lu, Y. Ling, W. Sun, et al., Environ. Pollut. 308 (2022) 119673.  doi: 10.1016/j.envpol.2022.119673
    

25. [25]

    X. Luo, B. Zhang, Y. Lu, et al., J. Hazard. Mater. 421 (2022) 126682.  doi: 10.1016/j.jhazmat.2021.126682
    

26. [26]

    H.D.M. Tran, S. Boivin, H. Kodamatani, et al., Chemosphere 286 (2022) 131682.  doi: 10.1016/j.chemosphere.2021.131682
    

27. [27]

    R. Shankar, W.J. Shim, J.G. An, U.H. Yim, Water Res. 68 (2015) 304–315.  doi: 10.1016/j.watres.2014.10.012
    

28. [28]

    W. Qiu, M. Zheng, J. Sun, et al., Sci. Total Environ. 651 (2019) 1457–1468.  doi: 10.1016/j.scitotenv.2018.09.315
    

29. [29]

    Y. Zhang, K. Huang, Y. Zhu, et al., RSC Adv. 12 (2022) 10088–10096.  doi: 10.1039/d2ra00199c
    

30. [30]

    X. Zeng, Y. Meng, X. Sun, et al., J. Environ. Chem. Eng. 9 (2021) 106608.  doi: 10.1016/j.jece.2021.106608
    

31. [31]

    X. Ao, W. Wang, W. Sun, et al., Water Res. 203 (2021) 117458.  doi: 10.1016/j.watres.2021.117458
    

32. [32]

    K. Guo, Z. Wu, S. Yan, et al., Water Res. 147 (2018) 184–194.  doi: 10.1016/j.watres.2018.08.048
    

33. [33]

    H. Milh, X. Yu, D. Cabooter, R. Dewil, Sci. Total Environ. 764 (2021) 144510.  doi: 10.1016/j.scitotenv.2020.144510
    

34. [34]

    H. Yang, Y. Li, Y. Chen, et al., Water Environ. Res. 91 (2019) 1576–1588.  doi: 10.1002/wer.1144
    

35. [35]

    H. Xue, S. Gao, N. Zheng, et al., Water Sci. Technol. 79 (2019) 2387–2394.  doi: 10.2166/wst.2019.240
    

36. [36]

    C.C. Lin, H.Y. Lin, Desalin. Water Treat. 167 (2019) 170–175.  doi: 10.5004/dwt.2019.24602
    

37. [37]

    J. Deng, G. Wu, S. Yuan, et al., J. Photochem. Photobiol. A: Chem. 371 (2019) 151–158.  doi: 10.1016/j.jphotochem.2018.10.043
    

38. [38]

    X. Zhang, K. Guo, Y. Wang, et al., Chem. Eng. J. 400 (2020) 125222.  doi: 10.1016/j.cej.2020.125222
    

39. [39]

    J. Lu, J. Li, J. Xu, et al., J. Water Process Eng. 44 (2021) 102324.  doi: 10.1016/j.jwpe.2021.102324
    

40. [40]

    H. Liu, Y. Gao, J. Wang, et al., Chemosphere 276 (2021) 130220.  doi: 10.1016/j.chemosphere.2021.130220
    

41. [41]

    D. Krakko, A. Illes, V. Licul-Kucera, et al., Chemosphere 275 (2021) 130080.  doi: 10.1016/j.chemosphere.2021.130080
    

42. [42]

    Q. Ping, T. Yan, L. Wang, et al., Water Res. 210 (2022) 118019.  doi: 10.1016/j.watres.2021.118019
    

43. [43]

    Q. Wu, Z. Que, Z. Li, et al., J. Hazard. Mater. 359 (2018) 414–420.  doi: 10.1016/j.jhazmat.2018.07.041
    

44. [44]

    C. Zhao, Y. Li, H. Chu, et al., J. Hazard. Mater. 419 (2021) 126466.  doi: 10.1016/j.jhazmat.2021.126466
    

45. [45]

    K. Saravanakumar, C.M. Park, Chem. Eng. J. 423 (2021) 130076.  doi: 10.1016/j.cej.2021.130076
    

46. [46]

    V.T. Le, V.A. Tran, D.L. Tran, et al., Chemosphere 270 (2021) 129417.  doi: 10.1016/j.chemosphere.2020.129417
    

47. [47]

    J. Lei, B. Chen, L. Zhou, et al., Chem. Eng. J. 400 (2020) 125902.  doi: 10.1016/j.cej.2020.125902
    

48. [48]

    J. Li, Z. Xia, D. Ma, et al., J. Colloid Interface Sci. 586 (2021) 243–256.  doi: 10.1016/j.jcis.2020.10.088
    

49. [49]

    Q. Chen, M. Zhang, J. Li, et al., Chem. Eng. J. 389 (2020) 124476.  doi: 10.1016/j.cej.2020.124476
    

50. [50]

    Q. Zhang, F. Han, Y. Yan, et al., Appl. Surf. Sci. 485 (2019) 547–553.  doi: 10.1016/j.apsusc.2019.04.185
    

51. [51]

    R. Du, P. Chen, Q. Zhang, G. Yu, Chemosphere 273 (2021) 128435.  doi: 10.1016/j.chemosphere.2020.128435
    

52. [52]

    X. Zeng, X. Sun, Y. Yu, et al., Chem. Eng. J. 378 (2019) 122226.  doi: 10.1016/j.cej.2019.122226
    

53. [53]

    L. Yang, Y. Xiang, F. Jia, et al., Appl. Catal. B: Environ. 292 (2021) 120198.  doi: 10.1016/j.apcatb.2021.120198
    

54. [54]

    Y. Tian, X. He, W. Chen, et al., Sci. Total Environ. 723 (2020) 138144.  doi: 10.1016/j.scitotenv.2020.138144
    

55. [55]

    O. Autin, C. Romelot, L. Rust, et al., Chemosphere 92 (2013) 745–751.  doi: 10.1016/j.chemosphere.2013.04.028
    

56. [56]

    S. Li, J. Hu, Water Res. 132 (2018) 320–330.  doi: 10.1016/j.watres.2017.12.065
    

57. [57]

    T.K. Kim, T. Kim, H. Park, et al., Chem. Eng. J. 394 (2020) 124803.  doi: 10.1016/j.cej.2020.124803
    

58. [58]

    S. Li, T. Huang, P. Du, et al., Water Res. 185 (2020) 116286.  doi: 10.1016/j.watres.2020.116286
    

59. [59]

    S. Guerra-Rodriguez, A.R. Lado Ribeiro, R.S. Ribeiro, et al., Sci. Total Environ. 770 (2021) 145299.  doi: 10.1016/j.scitotenv.2021.145299
    

60. [60]

    P. Chen, L. Blaney, G. Cagnetta, et al., Environ. Sci. Technol. 53 (2019) 1564–1575.  doi: 10.1021/acs.est.8b05827
    

61. [61]

    D. Cheng, H. Liu, E. Yang, et al., Sci. Total Environ. 773 (2021) 145102.  doi: 10.1016/j.scitotenv.2021.145102
    

62. [62]

    X. Liu, Y. Liu, S. Lu, et al., Chem. Eng. J. 385 (2020) 123987.  doi: 10.1016/j.cej.2019.123987
    

63. [63]

    W.K. Ye, F.X. Tian, B. Xu, et al., Sep. Purif. Technol. 280 (2022) 119846.  doi: 10.1016/j.seppur.2021.119846
    

64. [64]

    D.A. Armstrong, R.E. Huie, W.H. Koppenol, et al., Pure Appl. Chem. 87 (2015) 1139–1150.  doi: 10.1515/pac-2014-0502
    

65. [65]

    J. Lee, U. von Gunten, J.H. Kim, Environ. Sci. Technol. 54 (2020) 3064–3081.  doi: 10.1021/acs.est.9b07082
    

66. [66]

    T. Luukkonen, T. Heyninck, J. Rämö, U. Lassi, Water Res. 85 (2015) 275–285.  doi: 10.1016/j.watres.2015.08.037
    

67. [67]

    H. Zhang, L. Chen, P. Du, et al., Environ. Sci. Technol. 58 (2024) 3506–3519.
    

68. [68]

    M. Sturini, F. Maraschi, A. Cantalupi, et al., Materials 13 (2020) 537.  doi: 10.3390/ma13030537
    

69. [69]

    M. Eskandari, N. Goudarzi, S.G. Moussavi, Water Environ. J. 32 (2018) 58–66.  doi: 10.1111/wej.12291
    

70. [70]

    E.A. Serna-Galvis, Y. Avila-Torres, M. Ibanez, et al., Water 13 (2021) 2154.  doi: 10.3390/w13162154
    

71. [71]

    L. Pretali, F. Maraschi, A. Cantalupi, et al., Catalysts 10 (2020) 628.  doi: 10.3390/catal10060628
    

72. [72]

    A. Kaur, A. Umar, W.A. Anderson, S.K. Kansal, J. Photochem. Photobiol. A: Chem. 360 (2018) 34–43.  doi: 10.1016/j.jphotochem.2018.04.021
    

73. [73]

    A. Siddique, M.B. Tahir, I. Shahid, et al., Appl. Nanosci. 12 (2022) 1613–1626.  doi: 10.1007/s13204-021-02313-5
    

74. [74]

    L. Wolski, K. Grzelak, M. Munko, et al., Appl. Surf. Sci. 563 (2021) 150338.  doi: 10.1016/j.apsusc.2021.150338
    

75. [75]

    N. Kaur, A. Verma, I. Thakur, S. Basu, Chemosphere 276 (2021) 130180.  doi: 10.1016/j.chemosphere.2021.130180
    

76. [76]

    K. Qin, Q. Zhao, H. Yu, et al., Environ. Res. 199 (2021) 111360.  doi: 10.1016/j.envres.2021.111360
    

77. [77]

    T. Senasu, T. Narenuch, K. Wannakam, et al., J. Mater. Sci.: Mater. Electron. 31 (2020) 9685–9694.  doi: 10.1007/s10854-020-03514-4
    

78. [78]

    T. Chankhanittha, V. Somaudon, T. Photiwat, et al., J. Phys. Chem. Solids. 153 (2021) 109995.  doi: 10.1016/j.jpcs.2021.109995
    

79. [79]

    W. Liu, J. Zhou, J. Yao, Ecotoxicol. Environ. Saf. 190 (2020) 110062.  doi: 10.1016/j.ecoenv.2019.110062
    

80. [80]

    X. Zheng, S. Xu, Y. Wang, et al., J. Colloid Interface Sci. 527 (2018) 202–213.  doi: 10.1016/j.jcis.2018.05.054
    

81. [81]

    S. Moles, J. Berges, M.P. Ormad, et al., Environ. Sci. Pollut. Res. 28 (2021) 24167–24179.  doi: 10.1007/s11356-021-12542-4
    

82. [82]

    X. Huang, S. Wu, S. Tang, et al., J. Mol. Liq. 317 (2020) 113961.  doi: 10.1016/j.molliq.2020.113961
    

83. [83]

    C. Zhang, M. Jia, Z. Xu, et al., Chem. Eng. J. 430 (2022) 132652.  doi: 10.1016/j.cej.2021.132652
    

84. [84]

    Q. Wu, M.S. Siddique, Y. Guo, et al., Appl. Catal. B: Environ. 286 (2021) 119950.  doi: 10.1016/j.apcatb.2021.119950
    

85. [85]

    C. Yang, X. Wang, L. Zhang, et al., J. Taiwan Inst. Chem. Eng. 115 (2020) 117–127.  doi: 10.1016/j.jtice.2020.09.036
    

86. [86]

    L. Rizzo, Environ. Sci. Water Res. Technol. 8 (2022) 2145–2169.  doi: 10.1039/d2ew00146b
    

87. [87]

    H. Luo, Y. Zeng, D. He, X. Pan, Chem. Eng. J. 407 (2021) 127191.  doi: 10.1016/j.cej.2020.127191
    

88. [88]

    Y. Jiang, J. Ran, K. Mao, et al., Ecotoxicol. Environ. Saf. 236 (2022) 113464.  doi: 10.1016/j.ecoenv.2022.113464
    

89. [89]

    S.K. Mondal, A.K. Saha, A. Sinha, J. Cleaner Prod. 171 (2018) 1203–1214.  doi: 10.1016/j.jclepro.2017.10.091
    

90. [90]

    H. Dan, Y. Kong, Q. Yue, et al., Chem. Eng. J. 420 (2021) 127634.  doi: 10.1016/j.cej.2020.127634
    

91. [91]

    W. He, Z. Li, S. Lv, et al., Chem. Eng. J. 409 (2021) 128274.  doi: 10.1016/j.cej.2020.128274
    

92. [92]

    W. Li, Y. Wang, J. Chen, et al., Appl. Catal. B: Environ. 302 (2022) 120882.  doi: 10.1016/j.apcatb.2021.120882
    

93. [93]

    A. Hassani, J. Scaria, F. Ghanbari, P.V. Nidheesh, Environ. Res. 217 (2023) 114789.  doi: 10.1016/j.envres.2022.114789
    

94. [94]

    J. Yang, M. Zhu, D.D. Dionysiou, Water Res. 189 (2021) 116627.  doi: 10.1016/j.watres.2020.116627
    

95. [95]

    Y. Sun, D.W. Cho, N.J.D. Graham, et al., Sci. Total Environ. 664 (2019) 312–321.  doi: 10.1016/j.scitotenv.2019.02.006
    

96. [96]

    E. Ngumba, A. Gachanja, T. Tuhkanen, Water Environ. J. 34 (2020) 692–703.  doi: 10.1111/wej.12612
    

97. [97]

    L. Wang, J. Wei, Y. Li, et al., Chem. Eng. J. 477 (2023) 147051.  doi: 10.1016/j.cej.2023.147051
    

98. [98]

    T. Luukkonen, S.O. Pehkonen, Crit. Rev. Environ. Sci. Technol. 47 (2017) 1–39.  doi: 10.1080/10643389.2016.1272343
    

99. [99]

    X. Ao, X. Zhang, S. Li, et al., J. Hazard. Mater. 445 (2023) 130480.  doi: 10.1016/j.jhazmat.2022.130480
    

100. [100]

     Z. Diao, J. Jin, M. Zou, et al., Sep. Purif. Technol. 278 (2021) 119620.  doi: 10.1016/j.seppur.2021.119620
     

101. [101]

     Z.H. Diao, S.T. Huang, X. Chen, et al., J. Cleaner Prod. 330 (2022) 129806.  doi: 10.1016/j.jclepro.2021.129806
     

102. [102]

     J. Wu, J. Bai, Z. Wang, et al., Environ. Technol. 43 (2022) 95–106.  doi: 10.1080/09593330.2020.1779353
     

103. [103]

     H. Tang, Z. Dai, X. Xie, et al., Chem. Eng. J. 356 (2019) 472–482.  doi: 10.1016/j.cej.2018.09.066
     

104. [104]

     Y. h. Tian, N. Jia, L. Zhou, et al., Chemosphere 288 (2022) 132627.  doi: 10.1016/j.chemosphere.2021.132627
     

105. [105]

     D. Li, Z. Feng, B. Zhou, et al., Sci. Total Environ. 844 (2022) 157162.  doi: 10.1016/j.scitotenv.2022.157162
     

106. [106]

     P. Wang, H. Zhang, Z. Wu, et al., Chin. Chem. Lett. 34 (2023) 108722.  doi: 10.1016/j.cclet.2023.108722
     

107. [107]

     F. Wang, Y. Feng, P. Chen, et al., Appl. Catal. B: Environ. 227 (2018) 114–122.  doi: 10.1016/j.apcatb.2018.01.024
     

108. [108]

     G. Wang, Y. Li, J. Dai, N. Deng, Environ. Sci. Pollut. Res. 29 (2022) 48522–48538.  doi: 10.1007/s11356-022-19269-w
     

109. [109]

     H. Abdelraouf, J. Ding, J. Ren, et al., Process Saf. Environ. Prot. 168 (2022) 892–906.  doi: 10.1016/j.psep.2022.10.069
     

110. [110]

     M. Kumaresan, V. Saravanan, M. Swaminathan, Inorg. Chem. Commun. 142 (2022) 109706.  doi: 10.1016/j.inoche.2022.109706
     

111. [111]

     K. Jutarvutikul, C. Sakulthaew, C. Chokejaroenrat, et al., Aquacult. Eng. 94 (2021) 102174.  doi: 10.1016/j.aquaeng.2021.102174
     

112. [112]

     A.S. Giri, A.K. Golder, J. Environ. Sci. 80 (2019) 82–92.  doi: 10.1016/j.jes.2018.09.016
     

113. [113]

     C. Wang, J. Zhang, J. Du, et al., J. Hazard. Mater. 416 (2021) 125893.  doi: 10.1016/j.jhazmat.2021.125893
     

114. [114]

     G. Harini, M.K. Okla, I.A. Alaraidh, et al., Chemosphere 303 (2022) 134963.  doi: 10.1016/j.chemosphere.2022.134963
     

115. [115]

     X. Ao, W. Liu, W. Sun, et al., Chem. Eng. J. 345 (2018) 87–97.  doi: 10.1016/j.cej.2018.03.133
     

116. [116]

     Y. Qi, R. Qu, J. Liu, et al., Chemosphere 237 (2019) 124484.  doi: 10.1016/j.chemosphere.2019.124484
     

117. [117]

     S.P. Asu, N.K. Sompalli, S. Kuppusamy, et al., Mater. Today Sustain. 19 (2022) 100189.
     

118. [118]

     N. Yin, H. Chen, X. Yuan, et al., J. Hazard. Mater. 436 (2022) 129317.  doi: 10.1016/j.jhazmat.2022.129317
     

119. [119]

     H. Guo, N. Gao, Y. Yang, Y. Zhang, Chem. Eng. J. 292 (2016) 82–91.  doi: 10.1016/j.cej.2016.01.009
     

120. [120]

     M. Kamagate, A.A. Assadi, T. Kone, et al., J. Hazard. Mater. 346 (2018) 159–166.  doi: 10.1016/j.jhazmat.2017.12.011
     

121. [121]

     Y. Park, S. Kim, J. Kim, et al., Water 14 (2022) 958.  doi: 10.3390/w14060958
     

122. [122]

     F.H. Borba, A. Schmitz, L. Pellenz, et al., J. Environ. Chem. Eng. 6 (2018) 6979–6988.  doi: 10.1016/j.jece.2018.10.068
     

123. [123]

     Y. Zhu, M. Wei, Z. Pan, et al., Sci. Total Environ. 705 (2020) 135960.  doi: 10.1016/j.scitotenv.2019.135960
     

124. [124]

     S. Li, J.Y. Hu, J. Hazard. Mater. 318 (2016) 134–144.  doi: 10.1016/j.jhazmat.2016.05.100
     

125. [125]

     F. Tan, D. Sun, J. Gao, et al., J. Hazard. Mater. 244 (2013) 750–757.
     

126. [126]

     Z. Li, X. Yuan, H. Tang, et al., Environ. Sci. Water Res. Technol. 8 (2022) 2744–2760.  doi: 10.1039/d2ew00320a
     

127. [127]

     A. Wang, H. Wang, H. Deng, et al., Appl. Catal. B: Environ. 248 (2019) 298–308.  doi: 10.1016/j.apcatb.2019.02.034
     

128. [128]

     Y. Yu, K. Liu, Y. Zhang, et al., Int. J. Environ. Res. Public Health 19 (2022) 4793.  doi: 10.3390/ijerph19084793
     

129. [129]

     F. Wang, X. Yu, M. Ge, S. Wu, Chem. Eng. J. 384 (2020) 123381.  doi: 10.1016/j.cej.2019.123381
     

130. [130]

     O. Gomes Junior, V.M. Silva, A.E.H. Machado, et al., J. Environ. Manage. 213 (2018) 20–26.  doi: 10.1016/j.jenvman.2018.02.041