1. State Key Laboratory of Separation Membranes and Membrane Processes, Tiangong University, Tianjin 300387, China 2. Shandong Sinocera Functional Materials Co., Ltd., Dongying 257091, China
Combining molecular imprinting technique with titanium dioxide (TiO2) photocatalysis technique can improve the degradation ability and selectivity of TiO2 nanoparticles towards pollutants. In this work, methyl orange-imprinted polysiloxane particles (MIPs) were synthesized using TiO2 as matrix and silane as functional monomers. The adsorption capacity (Qe) of MIPs was 20.48 mg·g−1, while the imprinting efficiency (IE) was 3.4. Such MIPs exhibited stable imprinting efficiencies and adsorption efficiencies towards methyl orange (MO) in the multi-cycle stability test. Photocatalytic degradation performances of both MIPs and non-imprinted polysiloxane particles (NIPs) were investigated. Compared with NIPs, MIPs exhibited better photocatalytic degradation performance towards MO, with the degradation efficiency of 98.8% in 12 min and the apparent rate constant (Kobs) of 0.077 min−1. The interaction between silane and MO was also studied through molecular dynamics simulation. This work provides new insights into the use of silane for the synthesis of MIPs as well as the molecular imprinting technique for applications in the field of TiO2 photocatalysis.
S, Bhogal K, Kaur I, Mohiuddin et al.. Hollow porous molecularly imprinted polymers as emerging adsorbents.Environmental Pollution, 2021, 288: 117775 https://doi.org/10.1016/j.envpol.2021.117775
2
Y J, Cao T R, Sheng Z, Yang et al.. Synthesis of molecular-imprinting polymer coated magnetic nanocomposites for selective capture and fast removal of environmental tricyclic analogs.Chemical Engineering Journal, 2021, 426: 128678 https://doi.org/10.1016/j.cej.2021.128678
3
E, Mazzotta Giulio T, Di S, Mariani et al.. Vapor-phase synthesis of molecularly imprinted polymers on nanostructured materials at room-temperature.Small, 2023, 19(38): 2302274 https://doi.org/10.1002/smll.202302274
4
L J, Geng H F, Wang M Y, Liu et al.. Research progress on preparation methods and sensing applications of molecularly imprinted polymer‒aptamer dual recognition elements.Science of the Total Environment, 2024, 912: 168832 https://doi.org/10.1016/j.scitotenv.2023.168832
5
O, Erdem I, Es Y, Saylan et al.. In situ synthesis and dynamic simulation of molecularly imprinted polymeric nanoparticles on a micro-reactor system.Nature Communications, 2023, 14(1): 4840 https://doi.org/10.1038/s41467-023-40413-8
6
M, Pesavento D, Merli R, Biesuz et al.. A MIP-based low-cost electrochemical sensor for 2-furaldehyde detection in beverages.Analytica Chimica Acta, 2021, 1142: 201–210 https://doi.org/10.1016/j.aca.2020.10.059
7
X N, Dong C C, Zhang X, Du et al.. Recent advances of nanomaterials-based molecularly imprinted electrochemical sensors.Nanomaterials, 2022, 12(11): 1913 https://doi.org/10.3390/nano12111913
8
H, Afsharara E, Asadian B, Mostafiz et al.. Molecularly imprinted polymer-modified carbon paste electrodes (MIP-CPE): a review on sensitive electrochemical sensors for pharmaceutical determinations.TrAC Trends in Analytical Chemistry, 2023, 160: 116949 https://doi.org/10.1016/j.trac.2023.116949
9
Y, Pan D, Shan L L, Ding et al.. Developing a generally applicable electrochemical sensor for detecting macrolides in water with thiophene-based molecularly imprinted polymers.Water Research, 2021, 205: 117670 https://doi.org/10.1016/j.watres.2021.117670
10
L T, Zhong J Q, Zhai Y, Ma et al.. Molecularly imprinted polymers with enzymatic properties reduce cytokine release syndrome.ACS Nano, 2022, 16(3): 3797–3807 https://doi.org/10.1021/acsnano.1c08297
11
L B, Wan H, Liu C X, Huang et al.. Enzyme-like MOFs: synthetic molecular receptors with high binding capacity and their application in selective photocatalysis.Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2020, 8(48): 25931–25940 https://doi.org/10.1039/D0TA09873F
12
Sum Bui B, Tse T, Auroy K Haupt . Fighting antibiotic-resistant bacteria: promising strategies orchestrated by molecularly imprinted polymers.Angewandte Chemie International Edition, 2022, 61(8): e202106493 https://doi.org/10.1002/anie.202106493
13
S, Piletsky F, Canfarotta A, Poma et al.. Molecularly imprinted polymers for cell recognition.Trends in Biotechnology, 2020, 38(4): 368–387 https://doi.org/10.1016/j.tibtech.2019.10.002
14
Z D, Wang X W, Fang N R, Sun et al.. A rational route to hybrid aptamer-molecularly imprinted magnetic nanoprobe for recognition of protein biomarkers in human serum.Analytica Chimica Acta, 2020, 1128: 1–10 https://doi.org/10.1016/j.aca.2020.06.036
15
G, Pilvenyte V, Ratautaite R, Boguzaite et al.. Molecularly imprinted polymers for the recognition of biomarkers of certain neurodegenerative diseases.Journal of Pharmaceutical and Biomedical Analysis, 2023, 228: 115343 https://doi.org/10.1016/j.jpba.2023.115343
16
L D, Jiang R, Lu L Ye . Towards detection of glycoproteins using molecularly imprinted nanoparticles and boronic acid-modified fluorescent probe.Polymers, 2019, 11(1): 173 https://doi.org/10.3390/polym11010173
17
Sum Bui B, Tse A, Mier K Haupt . Molecularly imprinted polymers as synthetic antibodies for protein recognition: the next generation.Small, 2023, 19(13): 2206453 https://doi.org/10.1002/smll.202206453
18
Z H, Song J H, Li W H, Lu et al.. Molecularly imprinted polymers based materials and their applications in chromatographic and electrophoretic separations.TrAC Trends in Analytical Chemistry, 2022, 146: 116504 https://doi.org/10.1016/j.trac.2021.116504
19
T, Esteves R, Viveiros J, Bandarra et al.. Molecularly imprinted polymer strategies for removal of a genotoxic impurity, 4-dimethylaminopyridine, from an active pharmaceutical ingredient post-reaction stream.Separation and Purification Technology, 2016, 163: 206–214 https://doi.org/10.1016/j.seppur.2016.01.053
20
W D, Xing Y L, Yan C, Wang et al.. MOFs self-assembled molecularly imprinted membranes with photoinduced regeneration ability for long-lasting selective separation.Chemical Engineering Journal, 2022, 437: 135128 https://doi.org/10.1016/j.cej.2022.135128
21
Y H, Cui Z Y, He Y, Xu et al.. Fabrication of molecularly imprinted polymers with tunable adsorption capability based on solvent-responsive cross-linker.Chemical Engineering Journal, 2021, 405: 126608 https://doi.org/10.1016/j.cej.2020.126608
22
Y, Sun W S Zheng . Surface molecular imprinting on polystyrene resin for selective adsorption of 4-hydroxybenzoic acid.Chemosphere, 2021, 269: 128762 https://doi.org/10.1016/j.chemosphere.2020.128762
23
G, Dykstra B, Reynolds R, Smith et al.. Electropolymerized molecularly imprinted polymer synthesis guided by an integrated data-driven framework for cortisol detection.ACS Applied Materials & Interfaces, 2022, 14(22): 25972–25983 https://doi.org/10.1021/acsami.2c02474
24
S, Pardeshi R Dhodapkar . Advances in fabrication of molecularly imprinted electrochemical sensors for detection of contaminants and toxicants.Environmental Research, 2022, 212: 113359 https://doi.org/10.1016/j.envres.2022.113359
25
Y L, Wu X L, Liu J Y, Cui et al.. Bioinspired synthesis of high-performance nanocomposite imprinted membrane by a polydopamine-assisted metal–organic method.Journal of Hazardous Materials, 2017, 323: 663–673 https://doi.org/10.1016/j.jhazmat.2016.10.030
26
J, Gao L, Yan Y, Yan et al.. Solvent-driven controllable molecularly imprinted membrane with switched selectivity and fast regenerability enabled by customized bifunctional monomers.Chemical Engineering Journal, 2022, 446: 136991 https://doi.org/10.1016/j.cej.2022.136991
27
Y, Qu L, Qin X G, Liu et al.. Reasonable design and sifting of microporous carbon nanosphere-based surface molecularly imprinted polymer for selective removal of phenol from wastewater.Chemosphere, 2020, 251: 126376 https://doi.org/10.1016/j.chemosphere.2020.126376
28
J, Lu Y Y, Qin Q, Zhang et al.. Antibacterial, high-flux and 3D porous molecularly imprinted nanocomposite sponge membranes for cross-flow filtration of emodin from analogues.Chemical Engineering Journal, 2019, 360: 483–493 https://doi.org/10.1016/j.cej.2018.12.014
29
Y, Yang X, Long H Q, Zhang et al.. Surface modification of lithium-ion sieves by silane coupling agent for improved adsorption performance.Separation and Purification Technology, 2024, 330: 125422 https://doi.org/10.1016/j.seppur.2023.125422
30
Z Q, Yuan Y F, Wu J X, Zeng et al.. Modified nano-SiO2/PU hydrophobic composite film prepared through in-situ coupling by KH550 for oil–water separation.Environmental Science and Pollution Research International, 2023, 30(18): 52958–52968 https://doi.org/10.1007/s11356-023-25900-1
31
Y Y, Wang H N, Ruan J, Zhang et al.. Recyclable and selective PVDF-based molecularly imprinted membrane combining mussel-inspired biomimetic strategy for dimethomorph elimination.Chemical Engineering Journal, 2023, 478: 147322 https://doi.org/10.1016/j.cej.2023.147322
32
D D, Liu Y P, Zang Z W, Hu et al.. Synthesis of silicone hydrogel for soft contact lens (SCLs) and sustainable release of dexamethasone.Reactive & Functional Polymers, 2023, 186: 105532 https://doi.org/10.1016/j.reactfunctpolym.2023.105532
33
Z Y, Yan S, Wang J L, Bi et al.. Strengthening waterborne acrylic resin modified with trimethylolpropane triacrylate and compositing with carbon nanotubes for enhanced anticorrosion.Advanced Composites and Hybrid Materials, 2022, 5(3): 2116–2130 https://doi.org/10.1007/s42114-022-00554-8
34
Y M, Hou P X, Shah V, Constantoudis et al.. A super liquid-repellent hierarchical porous membrane for enhanced membrane distillation.Nature Communications, 2023, 14(1): 6886 https://doi.org/10.1038/s41467-023-42204-7
35
V, Filipovic K L, Bristow L, Filipovic et al.. Sprayable biodegradable polymer membrane technology for cropping systems: challenges and opportunities.Environmental Science & Technology, 2020, 54(8): 4709–4711 https://doi.org/10.1021/acs.est.0c00909
36
S, Takeshita T Ono . Biopolymer‒polysiloxane double network aerogels.Angewandte Chemie International Edition, 2023, 62(41): e202306518 https://doi.org/10.1002/anie.202306518
37
B F, Guo Y J, Wang Z H, Qu et al.. Hydrosilylation adducts to produce wide-temperature flexible polysiloxane aerogel under ambient temperature and pressure drying.Small, 2024, 20(14): 2309272 https://doi.org/10.1002/smll.202309272
38
X L, Shi X Q, Fan Y B, Zhu et al.. Pushing detectability and sensitivity for subtle force to new limits with shrinkable nanochannel structured aerogel.Nature Communications, 2022, 13(1): 1119 https://doi.org/10.1038/s41467-022-28760-4
39
X D, Hu S S, Zhang B, Yang et al.. Preparation of ambient-dried multifunctional cellulose aerogel by freeze-linking technique.Chemical Engineering Journal, 2023, 477: 147044 https://doi.org/10.1016/j.cej.2023.147044
40
Y X, Chen G L, Zhang G Z, Zhang et al.. Rapid curing and self-stratifying lacquer coating with antifouling and anticorrosive properties.Chemical Engineering Journal, 2021, 421: 129755 https://doi.org/10.1016/j.cej.2021.129755
41
R Z, Chen Y S, Zhang Q Y, Xie et al.. Transparent polymer–ceramic hybrid antifouling coating with superior mechanical properties.Advanced Functional Materials, 2021, 31(19): 2011145 https://doi.org/10.1002/adfm.202011145
42
X, Peng Z F, Yuan H M, Zhao et al.. Preparation and mechanism of hydrophobic modified diatomite coatings for oil–water separation.Separation and Purification Technology, 2022, 288: 120708 https://doi.org/10.1016/j.seppur.2022.120708
43
D, Liu K Y, Zhao M, Qi et al.. Preparation of protein molecular-imprinted polysiloxane membrane using calcium alginate film as matrix and its application for cell culture.Polymers, 2018, 10(2): 170 https://doi.org/10.3390/polym10020170
44
W K, Cui K Y, Zhao J F, Wei et al.. Adsorption properties of dye imprinted polysiloxane composite microspheres using strong basic anion-exchange resin as matrix.Desalination and Water Treatment, 2013, 51(40−42): 7604–7611 https://doi.org/10.1080/19443994.2013.777943
45
R, Fiorenza Mauro A, Di M, Cantarella et al.. Preferential removal of pesticides from water by molecular imprinting on TiO2 photocatalysts.Chemical Engineering Journal, 2020, 379: 122309 https://doi.org/10.1016/j.cej.2019.122309
46
A, Wahab M A, Minhas H, Shaikh et al.. Enhancement in photocatalytic selectivity of TiO2 based nano-catalyst through molecular imprinting technology.Environmental Science and Pollution Research International, 2023, 30(58): 121929–121947 https://doi.org/10.1007/s11356-023-30747-7
47
L, Zhu X, Liu X, Wang et al.. Evaluation of photocatalytic selectivity of Ag/Zn modified molecularly imprinted TiO2 by multiwavelength measurement.Science of the Total Environment, 2020, 703: 134732 https://doi.org/10.1016/j.scitotenv.2019.134732
48
B, Tang Z M, Wang G H Zhao . Preferential and simultaneous removal of chlorophenoxy herbicide pollutants via double molecular imprinted TiO2 single crystalline surface.Chemical Engineering Journal, 2022, 446: 137142 https://doi.org/10.1016/j.cej.2022.137142
49
D P, Li R F, Yuan B H, Zhou et al.. Selective photocatalytic removal of sulfonamide antibiotics: the performance differences in molecularly imprinted TiO2 synthesized using four template molecules.Journal of Cleaner Production, 2023, 383: 135470 https://doi.org/10.1016/j.jclepro.2022.135470
50
L L, Li X Y, Zheng Y H, Chi et al.. Molecularly imprinted carbon nanosheets supported TiO2: strong selectivity and synergic adsorption–photocatalysis for antibiotics removal.Journal of Hazardous Materials, 2020, 383: 121211 https://doi.org/10.1016/j.jhazmat.2019.121211
51
B, Hess C, Kutzner der Spoel D, van et al.. GROMACS 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation.Journal of Chemical Theory and Computation, 2008, 4(3): 435–447 https://doi.org/10.1021/ct700301q
52
M S, Barhaghi J J Potoff . Prediction of phase equilibria and Gibbs free energies of transfer using molecular exchange Monte Carlo in the Gibbs ensemble.Fluid Phase Equilibria, 2019, 486: 106–118 https://doi.org/10.1016/j.fluid.2018.12.032
53
G, Bussi D, Donadio M Parrinello . Canonical sampling through velocity rescaling.Journal of Chemical Physics, 2007, 126(1): 014101 https://doi.org/10.1063/1.2408420
