Post-synthetic modification of aluminum trimesate and copper trimesate with TiO2 nanoparticles for photocatalytic applications
Source abstract
Abstract
Organic pollutants have been a significant source of concern in recent years due to their facile dissemination and harmful effects. In this work, two different metal-organic frameworks (MOFs) were initially prepared by hydrothermal treatment, namely aluminum trimesate (MIL-100(Al)) and copper trimesate (HKUST-1). These materials were subsequently submitted to a post-synthetic modification step to grow titania nanoparticles on their surface. Anatase nanoparticles with sizes around 5 nm were successfully anchored on MIL-100(Al), and the concentration of TiO2 in this sample was about 68 wt.%. This is the first time that this composite (TiO2@MIL-100(Al)) is reported in the literature. It showed an improved photocatalytic activity, removing 90% of methylene blue (k app = 1.29 h-1), 55% of sodium diclofenac (k app = 0.21 h-1), and 62% of ibuprofen (k app = 0.37 h-1) after four hours of illumination with UV-A light. A significant concentration (14 µM) of reactive oxygen species (ROS) was detected for this composite. HKUST-1 showed a structural collapse during its post-synthetic modification, leading to a non-porous material and providing fewer sites for the heterogeneous nucleation of titania. This behavior led to a low concentration of rutile nanoparticles on HKUST-1 (9 wt.%). However, the obtained composite (TiO2@HKUST) also showed an improved photoactivity compared to HKUST-1, increasing the photodegradation rates evaluated for methylene blue (0.05 h-1 vs. 0.29 h-1), sodium diclofenac (negligible vs. 0.03 h-1), and ibuprofen (0.01 h-1 vs. 0.02 h-1). This work brings new insights concerning the preparation of photocatalysts by growing semiconductor nanoparticles on trimesate-based MOFs.
Source: europepmc · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Advanced Photocatalysis Techniques · TiO2 Photocatalysis and Solar Cells · Catalytic Processes in Materials Science
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References (92)
Show source-provided references
1. Hu H, Chang M, Zhang M et al (2017) A new insight into PAM/graphene-based adsorption of water-soluble aromatic pollutants. J Mater Sci 52:8650–8664. https://doi.org/10.1007/s10853-017-1090-x10.1007/s10853-017-1090-x ↗
2. Waiman CV, dell’Erba IE, Chesta CA, Gómez ML (2018) Hybrid mineral@silsesquioxane particles for water remediation: synthesis, characterization and application as adsorbent of As(V) and other water pollutants. J Mater Sci 53:12781–12794. https://doi.org/10.1007/s10853-018-2529-410.1007/s10853-018-2529-4 ↗
3. Wu Y, Qiu H, Sun J et al (2021) A silsesquioxane-based flexible polyimide aerogel with high hydrophobicity and good adsorption for liquid pollutants in wastewater. J Mater Sci 56:3576–3588. https://doi.org/10.1007/s10853-020-05460-210.1007/s10853-020-05460-2 ↗
4. Khan NA, Hasan Z, Jhung SH (2013) Adsorptive removal of hazardous materials using metal–organic frameworks (MOFs): a review. J Hazard Mater 244–245:444–456. https://doi.org/10.1016/j.jhazmat.2012.11.01110.1016/j.jhazmat.2012.11.011 ↗
5. Thakur P, Ballard S, Nelson R (2013) An overview of Fukushima radionuclides measured in the northern hemisphere. Sci Total Environ 458–460:577–613. https://doi.org/10.1016/j.scitotenv.2013.03.10510.1016/j.scitotenv.2013.03.105 ↗
6. Ekino S, Susa M, Ninomiya T et al (2007) Minamata disease revisited: an update on the acute and chronic manifestations of methyl mercury poisoning. J Neurol Sci 262:131–144. https://doi.org/10.1016/j.jns.2007.06.03610.1016/j.jns.2007.06.036 ↗
7. Quadra GR, Silva PSA, Paranaíba JR et al (2019) Investigation of medicines consumption and disposal in Brazil: a study case in a developing country. Sci Total Environ 671:505–509. https://doi.org/10.1016/j.scitotenv.2019.03.33410.1016/j.scitotenv.2019.03.334 ↗
8. Gadipelly C, Pérez-González A, Yadav GD et al (2014) Pharmaceutical industry wastewater: review of the technologies for water treatment and reuse. Ind Eng Chem Res 53:11571–11592. https://doi.org/10.1021/ie501210j10.1021/ie501210j ↗
9. Bhadra BN, Jhung SH (2018) Adsorptive removal of wide range of pharmaceuticals and personal care products from water using bio-MOF-1 derived porous carbon. Microp Mesop Mater 270:102–108. https://doi.org/10.1016/j.micromeso.2018.05.00510.1016/j.micromeso.2018.05.005 ↗
10. Huang J, Huang D, Zeng F et al (2021) Photocatalytic MOF fibrous membranes for cyclic adsorption and degradation of dyes. J Mater Sci 56:3127–3139. https://doi.org/10.1007/s10853-020-05473-x10.1007/s10853-020-05473-x ↗
11. Van Boeckel TP, Gandra S, Ashok A et al (2014) Global antibiotic consumption 2000 to 2010: an analysis of national pharmaceutical sales data. Lancet Infect Dis 14:742–750. https://doi.org/10.1016/S1473-3099(14)70780-710.1016/S1473-3099(14)70780-7 ↗
12. Jabbari V, Veleta JM, Zarei-Chaleshtori M et al (2016) Green synthesis of magnetic MOF@GO and MOF@CNT hybrid nanocomposites with high adsorption capacity towards organic pollutants. Chem Eng J 304:774–783. https://doi.org/10.1016/j.cej.2016.06.03410.1016/j.cej.2016.06.034 ↗
13. Holkar CR, Jadhav AJ, Pinjari DV et al (2016) A critical review on textile wastewater treatments: possible approaches. J Environ Manage 182:351–366. https://doi.org/10.1016/j.jenvman.2016.07.09010.1016/j.jenvman.2016.07.090 ↗
14. Moore N, Bosco-Levy P, Thurin N et al (2021) NSAIDs and COVID-19: a systematic review and meta-analysis. Drug Saf 44:929–938. https://doi.org/10.1007/s40264-021-01089-510.1007/s40264-021-01089-5 ↗
15. González Peña OI, López Zavala MÁ, Cabral Ruelas H (2021) Pharmaceuticals market, consumption trends and disease incidence are not driving the pharmaceutical research on water and wastewater. Int J Environ Res Public Health. https://doi.org/10.3390/ijerph1805253210.3390/ijerph18052532 ↗
16. Magdy YH, Altaher H (2018) Kinetic analysis of the adsorption of dyes from high strength wastewater on cement kiln dust. J Environ Chem Eng 6:834–841. https://doi.org/10.1016/j.jece.2018.01.00910.1016/j.jece.2018.01.009 ↗
17. Vacchi FI, Von der Ohe PC, de Albuquerque AF et al (2016) Occurrence and risk assessment of an azo dye—the case of disperse Red 1. Chemosphere 156:95–100. https://doi.org/10.1016/j.chemosphere.2016.04.12110.1016/j.chemosphere.2016.04.121 ↗
18. Chan SHS, Wu TY, Juan JC, Teh CY (2011) Recent developments of metal oxide semiconductors as photocatalysts in advanced oxidation processes (AOPs) for treatment of dye waste-water. J Chem Technol Biotechnol 86:1130–115810.1002/jctb.2636 ↗
19. Sen TK, Afroze S, Ang HM (2011) Equilibrium, kinetics and mechanism of removal of methylene blue from aqueous solution by adsorption onto pine cone biomass of Pinus radiata. Water Air Soil Pollut 218:499–515. https://doi.org/10.1007/s11270-010-0663-y10.1007/s11270-010-0663-y ↗
20. JianLong W, Hai C (2020) Catalytic ozonation for water and wastewater treatment: recent advances and perspective. Sci Total Environ 704:135249. https://doi.org/10.1016/j.scitotenv.2019.13524910.1016/j.scitotenv.2019.135249 ↗
21. Della Rocca DG, Peralta RM, Peralta RA et al (2021) Adding value to aluminosilicate solid wastes to produce adsorbents, catalysts and filtration membranes for water and wastewater treatment. J Mater Sci 56:1039–1063. https://doi.org/10.1007/s10853-020-05276-010.1007/s10853-020-05276-0 ↗
22. Silveira JV, Moraes EC, Moura JVB et al (2020) Mo-doped WO3 nanowires for adsorbing methylene blue dye from wastewater. J Mater Sci 55:6429–6440. https://doi.org/10.1007/s10853-020-04472-210.1007/s10853-020-04472-2 ↗
23. Song L, Li C, Chen W et al (2020) Highly efficient MnO2/reduced graphene oxide hydrogel motors for organic pollutants removal. J Mater Sci 55:1984–1995. https://doi.org/10.1007/s10853-019-04076-510.1007/s10853-019-04076-5 ↗
24. Zhao J, Zhang H, Jia S et al (2021) Z-scheme Bi2MoO6 nanoplate-decorated flower-like Bi12SiO2O for efficient photocatalytic degradation of organic pollutants. J Mater Sci 56:15241–15257. https://doi.org/10.1007/s10853-021-06263-910.1007/s10853-021-06263-9 ↗
25. Palhares HG, Gonçalves BS, Silva LMC et al (2020) Clarifying the roles of hydrothermal treatment and silica addition to synthesize TiO2-based nanocomposites with high photocatalytic performance. J Sol-Gel Sci Technol 95:119–135. https://doi.org/10.1007/s10971-020-05265-410.1007/s10971-020-05265-4 ↗
26. Hu H, Chang M, Wang X, Chen D (2017) Cotton fabric-based facile solar photocatalytic purification of simulated real dye wastes. J Mater Sci 52:9922–9930. https://doi.org/10.1007/s10853-017-1107-510.1007/s10853-017-1107-5 ↗
27. Gonçalves BS, Palhares HG, de Souza TCC et al (2019) Effect of the carbon loading on the structural and photocatalytic properties of reduced graphene oxide–TiO2 nanocomposites prepared by hydrothermal synthesis. J Mater Res Technol 8:6262–6274. https://doi.org/10.1016/j.jmrt.2019.10.02010.1016/j.jmrt.2019.10.020 ↗
28. Gonçalves BS, de Souza TCC, de Castro VG et al (2019) Solvent effect on the structure and photocatalytic behavior of TiO2–RGO nanocomposites. J Mater Res 34:3918–3930. https://doi.org/10.1557/jmr.2019.34210.1557/jmr.2019.342 ↗
29. Wen Y, Feng M, Zhang P et al (2021) Metal organic frameworks (MOFs) as photocatalysts for the degradation of agricultural pollutants in water. ACS ES&T Eng 1:804–826. https://doi.org/10.1021/acsestengg.1c0005110.1021/acsestengg.1c00051 ↗
30. Hussain MZ, Yang Z, Huang Z et al (2021) Recent advances in metal–organic frameworks derived nanocomposites for photocatalytic applications in energy and environment. Adv Sci 8:1–30. https://doi.org/10.1002/advs.20210062510.1002/advs.202100625 ↗
31. Belousov AS, Suleimanov EV (2021) Application of metal–organic frameworks as an alternative to metal oxide-based photocatalysts for the production of industrially important organic chemicals. Green Chem 23:6172–6204. https://doi.org/10.1039/d1gc01690c10.1039/d1gc01690c ↗
32. Wang Q, Gao Q, Al-Enizi AM et al (2020) Recent advances in MOF-based photocatalysis: environmental remediation under visible light. Inorg Chem Front 7:300–339. https://doi.org/10.1039/c9qi01120j10.1039/c9qi01120j ↗
33. Gautam S, Agrawal H, Thakur M et al (2020) Metal oxides and metal organic frameworks for the photocatalytic degradation: a review. J Environ Chem Eng 8:103726. https://doi.org/10.1016/j.jece.2020.10372610.1016/j.jece.2020.103726 ↗
34. Hejazi R, Mahjoub AR, Khavar AHC, Khazaee Z (2020) Fabrication of novel type visible-light-driven TiO2@MIL-100 (Fe) microspheres with high photocatalytic performance for removal of organic pollutants. J Photochem Photobiol A Chem 400:112644. https://doi.org/10.1016/j.jphotochem.2020.11264410.1016/j.jphotochem.2020.112644 ↗
35. Li Y, Jiang J, Fang Y et al (2018) TiO2 nanoparticles anchored onto the metal–organic framework NH2-MIL-88B(Fe) as an adsorptive photocatalyst with enhanced fenton-like degradation of organic pollutants under visible light irradiation. ACS Sustain Chem Eng 6:16186–16197. https://doi.org/10.1021/acssuschemeng.8b0296810.1021/acssuschemeng.8b02968 ↗
36. Tang Y, Yin X, Mu M et al (2020) Anatase TiO2@MIL-101(Cr) nanocomposite for photocatalytic degradation of bisphenol A. Colloids Surfaces A Physicochem Eng Asp 596:124745. https://doi.org/10.1016/j.colsurfa.2020.12474510.1016/j.colsurfa.2020.124745 ↗
37. Sun Z, Wang M, Fan J et al (2021) TiO2@MIL-101(Cr) nanocomposites as an efficient photocatalyst for degradation of toluene. Adv Compos Hybrid Mater. https://doi.org/10.1007/s42114-021-00337-710.1007/s42114-021-00337-7 ↗
38. Xiaobo M, Xinyu L, Jie Z et al (2020) Heterostructured TiO2@HKUST-1 for the enhanced removal of methylene blue by integrated adsorption and photocatalytic degradation. Environ Technol (United Kingdom). https://doi.org/10.1080/09593330.2020.174529510.1080/09593330.2020.1745295 ↗
39. Wang W, Ji Z, Zhang D et al (2021) TiO2 doped HKUST-1/CM film in the three-phase photocatalytic ammonia synthesis system. Ceram Int 47:19180–19190. https://doi.org/10.1016/j.ceramint.2021.03.26510.1016/j.ceramint.2021.03.265 ↗
40. Volkringer C, Popov D, Loiseau T et al (2009) Synthesis, single-crystal X-ray microdiffraction, and NMR characterizations of the giant pore metal–organic framework aluminum trimesate MIL-100. Chem Mater 21:5695–5697. https://doi.org/10.1021/cm901983a10.1021/cm901983a ↗
41. Lin KS, Adhikari AK, Ku CN et al (2012) Synthesis and characterization of porous HKUST-1 metal–organic frameworks for hydrogen storage. Int J Hydrogen Energy 37:13865–1387110.1016/j.ijhydene.2012.04.105 ↗
42. Yang J, Wang J, Deng S, Li J (2016) Improved synthesis of trigone trimer cluster metal organic framework MIL-100Al by a later entry of methyl groups. Chem Commun 52:725–728. https://doi.org/10.1039/c5cc08450d10.1039/c5cc08450d ↗
43. Loiseau T, Volkringer C, Haouas M et al (2015) Crystal chemistry of aluminium carboxylates: from molecular species towards porous infinite three-dimensional networks. Comptes Rendus Chim 18:1350–1369. https://doi.org/10.1016/j.crci.2015.08.00610.1016/j.crci.2015.08.006 ↗
44. Hu Y, Huang Z, Zhou L et al (2014) Synthesis of nanoscale titania embedded in MIL-101 for the adsorption and degradation of volatile pollutants with thermal desorption gas chromatography and mass spectrometry detection. J Sep Sci 37:1482–1488. https://doi.org/10.1002/jssc.20140010010.1002/jssc.201400100 ↗
45. López R, Gómez R (2012) Band-gap energy estimation from diffuse reflectance measurements on sol–gel and commercial TiO2: a comparative study. J Sol-Gel Sci Technol 61:1–7. https://doi.org/10.1007/s10971-011-2582-910.1007/s10971-011-2582-9 ↗
46. Nethercot AH (1974) Prediction of Fermi energies and photoelectric thresholds based on electronegativity concepts. Phys Rev Lett 33:1088–1091. https://doi.org/10.1103/PhysRevLett.33.108810.1103/PhysRevLett.33.1088 ↗
47. Mulliken RS (1934) A new electroaffinity scale; together with data on valence states and on valence ionization potentials and electron affinities. J Chem Phys 2:782–793. https://doi.org/10.1063/1.174939410.1063/1.1749394 ↗
48. Haouas M, Volkringer C, Loiseau T et al (2012) In situ NMR, ex situ XRD and SEM study of the hydrothermal crystallization of nanoporous aluminum trimesates MIL-96, MIL-100, and MIL-110. Chem Mater 24:2462–2471. https://doi.org/10.1021/cm300439e10.1021/cm300439e ↗
49. Loera-Serna S, Oliver-Tolentino MA, de Lourdes López-Núñez M, et al (2012) Electrochemical behavior of [Cu3(BTC)2] metal–organic framework: the effect of the method of synthesis. J Alloys Compd 540:113–120. https://doi.org/10.1016/j.jallcom.2012.06.03010.1016/j.jallcom.2012.06.030 ↗
50. Xu F, Yu Y, Yan J et al (2016) Ultrafast room temperature synthesis of GrO@HKUST-1 composites with high CO2 adsorption capacity and CO2/N2 adsorption selectivity. Chem Eng J 303:231–237. https://doi.org/10.1016/j.cej.2016.05.14310.1016/j.cej.2016.05.143 ↗
51. Feng Y, Wang C, Ke F et al (2018) MIL-100(Al) gels as an excellent platform loaded with doxorubicin hydrochloride for pH-triggered drug release and anticancer effect. Nanomaterials 8:446. https://doi.org/10.3390/nano806044610.3390/nano8060446 ↗
52. Ye R-P, Lin L, Chen C-C et al (2018) Synthesis of robust MOF-derived Cu/SiO2 catalyst with low copper loading via sol–gel method for the dimethyl oxalate hydrogenation reaction. ACS Catal 8:3382–3394. https://doi.org/10.1021/acscatal.8b0050110.1021/acscatal.8b00501 ↗
53. Crişan M, Brǎileanu A, Rǎileanu M et al (2008) Sol–gel S-doped TiO2 materials for environmental protection. J Non Cryst Solids 354:705–711. https://doi.org/10.1016/j.jnoncrysol.2007.07.08310.1016/j.jnoncrysol.2007.07.083 ↗
54. Vasconcelos DCL, Nunes EHM, Sabioni ACS et al (2012) Optical characterization of 316L stainless steel coated with sol–gel titania. J Non Cryst Solids. https://doi.org/10.1016/j.jnoncrysol.2012.07.03510.1016/j.jnoncrysol.2012.07.035 ↗
55. Yang J, Peterlik H, Lomoschitz M, Schubert U (2010) Preparation of mesoporous titania by surfactant-assisted sol–gel processing of acetaldoxime-modified titanium alkoxides. J Non Cryst Solids 356:1217–1227. https://doi.org/10.1016/j.jnoncrysol.2010.04.03510.1016/j.jnoncrysol.2010.04.035 ↗
56. Worrall SD, Bissett MA, Hill PI et al (2016) Metal–organic framework templated electrodeposition of functional gold nanostructures. Electrochim Acta 222:361–369. https://doi.org/10.1016/j.electacta.2016.10.18710.1016/j.electacta.2016.10.187 ↗
57. Li X, Lachmanski L, Safi S et al (2017) New insights into the degradation mechanism of metal–organic frameworks drug carriers. Sci Rep 7:1–11. https://doi.org/10.1038/s41598-017-13323-110.1038/s41598-017-13323-1 ↗
58. Zhu Y, Liu T, Ding C (1999) Structural characterization of TiO2 ultrafine particles. J Mater Res 14:442–446. https://doi.org/10.1557/JMR.1999.006310.1557/JMR.1999.0063 ↗
59. Song P, Zhang XY, Sun MX et al (2012) Graphene oxide modified TiO2 nanotube arrays: enhanced visible light photoelectrochemical properties. Nanoscale 4:1800–1804. https://doi.org/10.1039/c2nr11938b10.1039/c2nr11938b ↗
60. Todaro M, Alessi A, Sciortino L et al (2016) Investigation by raman spectroscopy of the decomposition process of HKUST-1 upon exposure to air. J Spectrosc. https://doi.org/10.1155/2016/807429710.1155/2016/8074297 ↗
61. Álvarez JR, Sánchez-González E, Pérez E et al (2017) Structure stability of HKUST-1 towards water and ethanol and their effect on its CO2 capture properties. Dalt Trans 46:9192–9200. https://doi.org/10.1039/c7dt01845b10.1039/c7dt01845b ↗
62. Prestipino C, Regli L, Vitillo JG et al (2006) Local structure of framework Cu(II) in HKUST-1 metallorganic framework: spectroscopic characterization upon activation and interaction with adsorbates. Chem Mater 18:1337–1346. https://doi.org/10.1021/cm052191g10.1021/cm052191g ↗
63. Zhao Z, Kou T, Zhang L et al (2018) Dealloying induced N-doping in spindle-like porous rutile TiO2 for enhanced visible light photocatalytic activity. Corros Sci 137:204–211. https://doi.org/10.1016/j.corsci.2018.03.04910.1016/j.corsci.2018.03.049 ↗
64. Nosaka Y, Nosaka AY (2016) Reconsideration of intrinsic band alignments within anatase and rutile TiO2. J Phys Chem Lett 7:431–43410.1021/acs.jpclett.5b02804 ↗
65. García Márquez A, Demessence A, Platero-Prats AE et al (2012) Green microwave synthesis of MIL-100(Al, Cr, Fe) nanoparticles for thin-film elaboration. Eur J Inorg Chem 100:5165–5174. https://doi.org/10.1002/ejic.20120071010.1002/ejic.201200710 ↗
66. Guerrero VV, Yoo Y, McCarthy MC, Jeong HK (2010) HKUST-1 membranes on porous supports using secondary growth. J Mater Chem 20:3938–3943. https://doi.org/10.1039/b924536g10.1039/b924536g ↗
67. Giovine R, Pourpoint F, Duval S et al (2018) The surprising stability of Cu3(btc)2 metal–organic framework under steam flow at high temperature. Cryst Growth Des 18:6681–6693. https://doi.org/10.1021/acs.cgd.8b0093110.1021/acs.cgd.8b00931 ↗
68. Canioni R, Roch-Marchal C, Sécheresse F et al (2011) Stable polyoxometalate insertion within the mesoporous metal organic framework MIL-100(Fe). J Mater Chem 21:1226–1233. https://doi.org/10.1039/c0jm02381g10.1039/c0jm02381g ↗
69. Tian H, Peng J, Du Q et al (2018) One-pot sustainable synthesis of magnetic MIL-100(Fe) with novel Fe3O4 morphology and its application in heterogeneous degradation. Dalt Trans 47:3417–3424. https://doi.org/10.1039/c7dt04819j10.1039/c7dt04819j ↗
70. Lv H, Zhao H, Cao T et al (2015) Efficient degradation of high concentration azo-dye wastewater by heterogeneous Fenton process with iron-based metal–organic framework. J Mol Catal A Chem 400:81–89. https://doi.org/10.1016/j.molcata.2015.02.00710.1016/j.molcata.2015.02.007 ↗
71. Li Y, Wen L, Tan T, Lv Y (2019) Sequential Co-immobilization of enzymes in metal–organic frameworks for efficient biocatalytic conversion of adsorbed CO2 to formate. Front Bioeng Biotechnol 7:394. https://doi.org/10.3389/fbioe.2019.0039410.3389/fbioe.2019.00394 ↗
72. Wang H, Yu T, Tan X et al (2016) Enhanced photocatalytic oxidation of isopropanol by HKUST-1@TiO2 core–shell structure with ultrathin anatase porous shell: toxic intermediate control. Ind Eng Chem Res 55:8096–8103. https://doi.org/10.1021/acs.iecr.6b0140010.1021/acs.iecr.6b01400 ↗
73. Sing KSW (1982) Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl Chem 54:2201–2218. https://doi.org/10.1351/pac19855704060310.1351/pac198557040603 ↗
74. Jenkins CA, Murphy DM, Rowlands CC, Egerton TA (1997) EPR study of spin-trapped free radical intermediates formed in the heterogeneously-assisted photodecomposition of acetaldehyde. J Chem Soc Perkin Trans 2:2479–2485. https://doi.org/10.1039/A702944F10.1039/A702944F ↗
75. Harbour JR, Hair ML (1978) Detection of superoxide ions in nonaqueous media. Generation by photolysis of pigment dispersions. J Phys Chem 82:1397–1399. https://doi.org/10.1021/j100501a01510.1021/j100501a015 ↗
76. Meilikhov M, Yusenko K, Esken D et al (2010) Metals@MOFs—Loading MOFs with metal nanoparticles for hybrid functions. Eur J Inorg Chem. https://doi.org/10.1002/ejic.20100047310.1002/ejic.201000473 ↗
77. Cheng H, Ma J, Zhao Z, Qi L (1995) Hydrothermal preparation of uniform nanosize rutile and anatase particles. Chem Mater 7:663–671. https://doi.org/10.1021/cm00052a01010.1021/cm00052a010 ↗
78. Hanaor DAH, Sorrell CC (2011) Review of the anatase to rutile phase transformation. J Mater Sci 46:855–874. https://doi.org/10.1007/s10853-010-5113-010.1007/s10853-010-5113-0 ↗
79. Zhang J, Zhou P, Liu J, Yu J (2014) New understanding of the difference of photocatalytic activity among anatase, rutile and brookite TiO2. Phys Chem Chem Phys 16:20382–20386. https://doi.org/10.1039/c4cp02201g10.1039/c4cp02201g ↗
80. Disanto AR, Wagner JG (1972) Pharmacokinetics of highly ionized drugs II: methylene blue—absorption, metabolism, and excretion in man and dog after oral administration. J Pharm Sci 61:1086–1090. https://doi.org/10.1002/jps.260061071010.1002/jps.2600610710 ↗
81. Licona KPM, de Geaquinto LR, Nicolini JV et al (2018) Assessing potential of nanofiltration and reverse osmosis for removal of toxic pharmaceuticals from water. J Water Process Eng 25:195–20410.1016/j.jwpe.2018.08.002 ↗
82. Oh S, Shin WS, Kim HT (2016) Effects of pH, dissolved organic matter, and salinity on ibuprofen sorption on sediment. Environ Sci Pollut Res 23:22882–22889. https://doi.org/10.1007/s11356-016-7503-610.1007/s11356-016-7503-6 ↗
83. Po HN, Senozan NM (2001) The Henderson-Hasselbalch equation: its history and limitations. J Chem Educ 78:1499–1503. https://doi.org/10.1021/ed078p149910.1021/ed078p1499 ↗
84. Stoll S, Schweiger A (2006) EasySpin, a comprehensive software package for spectral simulation and analysis in EPR. J Magn Reson 178:42–55. https://doi.org/10.1016/j.jmr.2005.08.01310.1016/j.jmr.2005.08.013 ↗
85. Zhao H, Joseph J, Zhang H et al (2001) Synthesis and biochemical applications of a solid cyclic nitrone spin trap: a relatively superior trap for detecting superoxide anions and glutathiyl radicals. Free Radic Biol Med 31:599–606. https://doi.org/10.1016/S0891-5849(01)00619-010.1016/S0891-5849(01)00619-0 ↗
86. Villamena FA (2017) EPR spin trapping. In: Villamena F (ed) Reactive species detection in biology, 2nd edn. Elsevier, Boston, pp 163–20210.1016/B978-0-12-420017-3.00004-9 ↗
87. Bilski P, Reszka K, Bilska M, Chignell CF (1996) Oxidation of the spin trap 5,5-dimethyl-1-pyrroline N-oxide by singlet oxygen in aqueous solution. J Am Chem Soc 118:1330–1338. https://doi.org/10.1021/ja952140s10.1021/ja952140s ↗
88. Scott MJ, Billiar TR, Stoyanovsky DA (2016) N-tert-butylmethanimine N-oxide is an efficient spin-trapping probe for EPR analysis of glutathione thiyl radical. Sci Rep 6:38773. https://doi.org/10.1038/srep3877310.1038/srep38773 ↗
89. Padilla Villavicencio M, Escobedo Morales A, de Ruiz Peralta M et al (2020) Ibuprofen photodegradation by Ag2O and Ag/Ag2O composites under simulated visible light irradiation. Catal Letters 150:2385–2399. https://doi.org/10.1007/s10562-020-03139-610.1007/s10562-020-03139-6 ↗
90. Binh NT, Thi PT, Le Hong HT et al (2015) Study on preparation and properties of a novel photo-catalytic material based on copper-centred metal–organic frameworks (Cu-MOF) and titanium dioxide. Int J Nanotechnol 12:447–45510.1504/IJNT.2015.067902 ↗
91. Vu CM, Nguyen VH, Thi HV et al (2020) Hybrid material based on TiO2, CuBTC, and magnetic particles as a novel photocatalyst for MB removal. J Chem Technol Biotechnol 95:2648–2655. https://doi.org/10.1002/jctb.645010.1002/jctb.6450 ↗
92. Chang N, Zhang H, Shi MS et al (2018) Regulation of the adsorption affinity of metal–organic framework MIL-101 via a TiO2 coating strategy for high capacity adsorption and efficient photocatalysis. Microp Mesop Mater 266:47–55. https://doi.org/10.1016/j.micromeso.2018.02.05110.1016/j.micromeso.2018.02.051 ↗