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The Application of Aqueous Recognition Molecularly Imprinted Polymers in Sample Pretreatment

Tianyu Zhou , Yanbo Wang , Yilin Zhao , Hongji Li , Chunbo Liu , Guangbo Che

Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (5) : 1124 -1135.

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Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (5) : 1124-1135 DOI: 10.7536/PC210604
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The Application of Aqueous Recognition Molecularly Imprinted Polymers in Sample Pretreatment
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Abstract

Molecularly imprinted polymers (MIPs) are artificially constructed materials that mimic the recognition mechanism of antigens and antibodies. The construction of MIPs with excellent aqueous recognition capacity has been a long-term challenge in molecular imprinting fields. In recent years, aqueous recognition MIPs have attracted extensive attention from analytical chemists, materials scientists and environmentalists due to their excellent aqueous recognition and anti-matrix interference ability. In this article, we summarize the preparation and application of aqueous recognition MIPs in sample pretreatment in recent years. Firstly, the construction principles, advantages of MIPs and challenges of MIPs in aqueous recognition are briefly introduced. Secondly, sample pretreatment and its importance are introduced. Thirdly, combined with various emerging materials and preparation techniques of MIPs, the application of aqueous recognition MIPs in sample pretreatment is comprehensively summarized from the perspective of sample pretreatment techniques involving solid phase extraction, dispersive solid phase extraction, magnetic solid phase extraction, solid phase microextraction, pipette tip solid phase extraction and stir bar adsorption extraction. Meanwhile, the advantages of various methods in the analysis of water environment samples are discussed in combination with material properties and analytical parameters. Finally, the challenges and future development trends in this field are presented from perspectives of the construction of aqueous recognition MIPs and sample pretreatment.

Contents

1 Introduction

2 Sample pretreatment techniques

2.1 Solid phase extraction

2.2 Dispersive solid phase extraction

2.3 Magnetic solid phase extraction

2.4 Solid phase microextraction

2.5 Pipette tip solid phase extraction

2.6 Stir bar adsorption extraction

2.7 Membrane protected solid phase extraction

3 Conclusion and outlook

Graphical abstract

Keywords

molecularly imprinted polymers / aqueous recognition / sample pretreatment / hydrophilic / water compatible

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Tianyu Zhou, Yanbo Wang, Yilin Zhao, Hongji Li, Chunbo Liu, Guangbo Che. The Application of Aqueous Recognition Molecularly Imprinted Polymers in Sample Pretreatment. Progress in Chemistry, 2022, 34(5): 1124-1135 DOI:10.7536/PC210604

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1 Introduction

The intrinsic mechanism of natural donor-receptor (antigen-antibody) interaction is elaborate supramolecular chemistry, and chemists have been exploring chemical methods to precisely construct synthetic surrogates (i.e., synthetic receptor/antibody) with receptor/antibody-like properties. Molecularly Imprinted Polymers (MIPs) was first proposed by Polyakov in 1931. It is an artificially constructed material that mimics the antigen-antibody recognition mechanism and has specific recognition of the target. It uses the synergistic effect of functional groups and stereochemistry to achieve specific recognition of the target by customizing the shape, size, and functional groups of the imprinting site complementary to the template molecule (Figure 1)[1][2⇓~4]. In general, MIPs can be directionally solidified around the template by covalent or non-covalent interaction with appropriate crosslinking monomers and functional monomers to construct imprinting sites complementary to the size, shape, and functional groups of the template[5]. As a chemically designed receptor, MIPs not only have recognition specificity, but also have the advantages of wide application and structural predetermination compared with natural receptors. More importantly, MIPs also have the advantages of low preparation cost, high physical and chemical stability, good reusability and great production potential.This makes MIPs have strong application potential in catalysis, electrical/optical/gas sensing, diagnosis/therapy, sample pretreatment and other fields, and is widely favored by material scientists, analytical chemists, food/environmental/biological workers[5⇓~7][8⇓~10][11][1,12][12⇓~14].
Although great strides have been made in the development of MIPs, obtaining MIPs with ideal selectivity in aqueous solution remains a long-standing challenge. In general, MIPs are prepared in aprotic organic or rich organic solvents, and often show ideal selectivity in the preparation environment, which greatly limits the selective analysis of targets in aqueous samples by MIPs, while most of the analytes are highly soluble in water or exist in water-rich systems (such as environmental water samples, beverages, biological liquids)[15⇓~17]. Therefore, compared with MIPs formed in rich organic solvents, it is of great practical significance to develop aqueous recognition MIPs that can meet the needs of food safety control, environmental quality monitoring, biological health analysis and other practical applications[15⇓~17]. Although there are various strategies to obtain aqueous recognition MIPs, they are mainly achieved in the following two ways. (1) Use hydrophilic raw materials, such as hydrophilic monomers or crosslinking agents, hydrophilic polymers that can be self-assembled, etc[18⇓~20]. (2) Controlling the stability of template-monomer complex in the aqueous imprinting system, such as adjusting the polarity or acidity of the environment, and introducing forces (π-π interaction, electrostatic interaction, host-guest interaction, covalent interaction, etc.) That are hardly disturbed by water molecules[16,17,21⇓ ~23]. In view of the fact that our research group has reviewed the progress and development trend of preparation strategies for aqueous phase recognition of MIPs in 2019, and further summarized the latest progress of preparation strategies for selective adsorbents (including MIPs materials) from the perspective of selective adsorption mechanism.The preparation strategies of aqueous recognition MIPs and selective adsorption materials have been systematically reviewed in the two reviews. Therefore, on the basis of the previous two reviews, this paper will summarize the application of aqueous recognition MIPs in analysis and detection from the perspective of sample pretreatment technology, especially the related work from 2019 to the present[16,17].
Sample pretreatment, also known as sample pretreatment, is a purification process of the sample to be analyzed before instrumental analysis, which mainly separates and enriches the target from the sample matrix, while reducing the interference of complex matrix components, so that the sample can be presented in a form compatible with instrumental analysis. Therefore, sample pretreatment is considered to be an essential link to improve the accuracy, stability and precision of analytical methods. Sample pretreatment methods, such as liquid-liquid extraction, solid phase extraction, membrane extraction, supercritical fluid extraction, QuEChERS, etc., are widely developed according to the complexity of the sample matrix and the state of the sample (gas, liquid, solid, or semi-solid), the physicochemical properties of the analysis (stability, solubility, polarity), and the purpose of the analysis (qualitative, quantitative, semi-quantitative). However, the real sample matrix contains trace amounts of target substances and a wide variety of impurities (such as proteins, polysaccharides, lipids, solid particles and small molecules with similar structures), which will lead to signal interference, instrument pollution, unexpected errors and other problems, seriously affecting the analysis effect[16]. Therefore, in order to reduce the matrix interference and improve the analytical performance, it is very beneficial to the accurate analysis of trace targets in complex samples by using appropriate selective adsorbents to extract low-content targets in the sample pretreatment process.
Although MIPs can selectively purify and enrich targets from complex samples while reducing complex matrix interference, water, as the dispersed phase of most environmental, food and biological samples, is inevitably present during sample pretreatment. Therefore, it is of great practical significance to combine aqueous recognition MIPs with a variety of sample pretreatment techniques for the selective analysis of trace targets in real samples. In 2014, Zhang Huiqi of Nankai University introduced the research progress of water-compatible MIPs in the field of biology, and introduced in detail his proposed method of controlled/living radical polymerization to prepare water-compatible MIPs[24]. In 2019, our research group reviewed the research progress and development trend of the preparation of aqueous recognition MIPs and their application in sample pretreatment[17]. In recent years (2019-present), the study of MIPs combined with a variety of sample pretreatment techniques (e.g., solid phase extraction, dispersive solid phase extraction, magnetic solid phase extrac- tion, solid phase microextraction, pipette tip solid phase extraction and stir bar sorptive extraction) has been widely reported in the analysis of aqueous samples with excellent analytical results (Table 1). However, at present, there is no report on the application of aqueous recognition MIPs in analysis and detection from the perspective of various sample pretreatment technologies. The close combination of new pretreatment technologies/separation methods/analysis strategies and excellent aqueous phase recognition MIPs will bring more outstanding contributions to the field of analysis and detection (such as broadening the scope of analysis, improving the performance of analysis and the diversity of analysis methods). Therefore, it is necessary to sort out all kinds of excellent research results, and propose more schemes for the preparation of more excellent aqueous recognition MIPs and their application in sample pretreatment, so as to facilitate the follow-up research, and also provide more choices and more accurate analysis results for the determination of trace targets in complex aqueous media samples.
The purpose of this paper is to review the preparation of aqueous recognition MIPs and their application in sample pretreatment in recent years. Firstly, the construction principle, advantages and the challenge of water phase recognition of MIPs are briefly introduced. Secondly, the sample pretreatment technology and its importance are introduced. Thirdly, the application of aqueous phase recognition MIPs in sample pretreatment was comprehensively summarized by combining various emerging materials and MIPs preparation technologies.Including solid phase extraction (SPE), dispersive SPE, magnetic SPE, solid phase microextraction (SPme), pipette tip SPE, stir bar sorptive extraction and membrane protected SPE. The advantages and disadvantages of various sample pretreatment techniques were discussed in combination with material properties and analytical parameters. Finally, the challenges and future trends in this field are presented.

2 Sample pretreatment technique

2.1 Solid phase extraction

Packed solid phase extraction (i.e. conventional solid phase extraction, usually denoted as SPE, and the process is shown in Fig. 2), as one of the most commonly used sample pretreatment techniques in trace analysis, has the advantages of simplicity, versatility, and high enrichment factor compared with traditional liquid-liquid extraction (LLE). The performance of adsorbent is the key factor that significantly affects the effect of SPE. Using MIPs as SPE adsorbent to construct molecularly imprinted solid phase extraction column can significantly reduce the matrix interference and further improve the precision and accuracy of the analysis method[25][26⇓~28]. MIPs with good hydrophilicity or aqueous phase recognition ability can be very convenient to directly enrich the target in aqueous medium samples, greatly simplify the extraction step and reduce the operation cost. More importantly, the hydrophilicity of MIPs enhances the permeability to the SPE column, which is beneficial to the full progress of the adsorption-desorption process[29,30]. Zhu et al. Synthesized a novel water-compatible ciprofloxacin MIPs in water using a green, non-toxic and environmentally friendly method[31]. Hydrophilic groups such as anion chlorine, hydroxyl and carbonyl oxygen introduced by the bifunctional monomer 1-allyl-3-vinyl imidazole chloride and 2-hydroxyethyl methacrylate in the imprinted material enable the polymer to adsorb target molecules in an aqueous solution through hydrogen bonding, electrostatic and π-π dipole interactions. The excellent selectivity and hydrophilicity of the MIPs make them very suitable to be used as SPE adsorbents to achieve efficient recognition and selective separation and enrichment of trace quinolone antibiotics (ciprofloxacin, levofloxacin and Pefloxacin mesylate) in complex matrices such as water, soil and pork samples. The established MIPs-SPE-HPLC-UV method showed good linearity in the range of (0.29~1.47)×105μg·L-1, and the recovery rate reached 87. 3% ~ 102.5%. The material has potential application value for selective recognition and enrichment of water-soluble pollutants in various complex matrices, and is of great significance for the design and preparation of novel imprinting materials with excellent affinity in aqueous media. Similarly, He et al. Synthesized pirimicarb MIP by bulk polymerization using bifunctional monomer allyl-β-cyclodextrin (allyl-β-CD) and methacrylic acid (MAA) or allyl-β-CD and acrylonitrile, and combined with SPE technology to achieve selective recognition and enrichment of pirimicarb in aqueous medium[32]. The method is simple, rapid and low-cost, and can effectively separate and enrich the target compound with only a small amount of solvent. Mohiuddin et al. Synthesized carbamazepine (CBZ) MIP using common MAA and ethylene glycol dimethacrylate (EGDMA) as monomers and crosslinking agents, and used it to construct a SPE column for the detection of CBZ and its metabolite oxcarbazepine (OXC) in water and biological samples combined with HPLC-UV[33]. The method achieved a wide linear range (1~500μg·L-1,R2>0.990), low relative standard deviation (RSD) < 3% and high recovery (CBZ (87% – 98%) and OXC (72% – 78%)) with LOD as low as 0.488μg·L-1 and 0.515μg·L-1 for CBZ and OXC. In addition, the method has a high reuse rate, the recovery rate of CBZ is still 94% -98% after 10 cycles, and the method can maintain a good effective binding capacity of CBZ and its structural analogue OXC in urine and blood samples in the presence of other interfering substances. This method provides an effective protocol for the targeted enrichment of low concentrations of CBZ and OXC in water and biological samples.
The SPE column constructed by MIPs with non-uniform particle size will lead to irregular liquid flow path, low extraction efficiency and poor repeatability due to insufficient contact between the non-uniform solid packing layer and the solution. Therefore, MIPs with uniform particle size prepared by suspension polymerization, emulsion polymerization, precipitation polymerization and other methods are more suitable for SPE fillers. Our group prepared hydrophilic molecularly imprinted resins (MIRs) with uniform particle size and excellent monodispersity by condensation of resorcinol, melamine and formaldehyde, and successfully used them as hydrophilic adsorbents to construct SPE columns, which achieved rapid and selective enrichment of six triazine herbicides in water diluted honey samples[34]. Fathi Til et al. Used acetonitrile/methanol (5 ∶ 1, V/V) as solvent and common alkenyl monomers as raw materials to prepare an environment-friendly MIPs for the extraction of sinapic acid in aqueous solution by precipitation polymerization, and used the MIPs as SPE filler to realize the selective extraction of sinapic acid in rapeseed meal[35]. This method can be used to selectively extract sinapinic acid from complex agricultural foods, low-cost food wastes and wastewater, and has high application potential. Similarly, Parisa et al. Synthesized a MIPs with high selective recognition effect for ceftazidime as an adsorbent for SPE[36]. The developed MISPE-HPLC method can realize the selective extraction of ceftazidime in human serum and urine samples, and effectively remove the interference peaks in the complex matrix.The recovery of ceftazidime in human serum and urine samples is 97% – 99% and 94% – 95%, respectively, and the linear range is as low as 25~800μg·L-1,LOD to 7μg·L-1. This study provides an effective, rapid and inexpensive method for the isolation of ceftazidime from biological fluids, which is valuable for the development of selective extraction and enrichment methods for other compounds. The combination of computational simulation and molecular imprinting lays a foundation for the establishment of a simple, rapid and convenient MISPE method[37⇓~39]. Yu et al. Combined computational simulation with molecular imprinting technique to prepare hydrophilic MIP microspheres with high affinity for chenodeoxycholic acid (CDCA) by using polyethylene glycol diacrylate 200 as hydrophilic crosslinking agent, and used it for CDCA in SPE crude bile[38]. The adsorption capacity of CDCA by CDCA-MIP was up to 49.86 mg·g-1, the imprinting factor was 2.72, and the recovery rate was up to 94.1% – 96.1%. The imprinted microspheres prepared by this method have high yield (> 90%) and hydrophilic surface. In addition to the selective extraction of CDCA from crude bile, this study also provides a new protocol for the rational design of water-compatible MIPs.
With the development of traditional molecular imprinting preparation technology and the innovation of new imprinting methods, a large number of new aqueous recognition MIPs combined with SPE technology have been widely used to extract various trace targets in food, environmental and biological samples.The satisfactory analytical parameters obtained prove that the MISPE technique can effectively reduce the matrix interference and improve the precision and accuracy of the method, and the aqueous phase identification of MIPs can further improve the performance of the method and broaden the application range of MISPE. Although some finished products of MISPE column have been developed, there are certain requirements for packing technology, particle uniformity and particle size, and there are some shortcomings such as time-consuming and labor-intensive column packing process, high cost of large sample analysis and testing.

2.2 Dispersive solid-phase extraction

Dispersive solid phase extraction (DSPE) is a solid phase extraction technique that significantly reduces the extraction time and simplifies the extraction process. In this type of technique, the extraction process is carried out in a liquid sample by using a dispersed material instead of a solid phase extraction column, disc, or cartridge[40]. Therefore, in the selective extraction of bulk water samples such as environmental water, DSPE combined with aqueous phase recognition of MIPs will present the advantages of rapid, simple and efficient enrichment, because in the process of DSPE, MIPs are directly dispersed in the sample solution.The hydrophilicity of MIPs is beneficial to the dispersion of MIPs in water, which effectively utilizes the advantages of hydrophilic MIPs in resisting matrix interference and specific adsorption, and increases the contact between MIPs and the target due to the rapid penetration of water molecules carrying the target into the hydrophilic imprinted pore wall of MICs[41,42]; Compared with the conventional SPE column, DSPE not only avoids operations such as column loading, but also avoids phenomena such as blockage or channeling of the SPE column. The typical process of MIPs combined with DSPE is shown in Figure 3[15].
Recently, Ding Lan et al. Constructed a solvent-responsive molecularly imprinted polymer (S-MIPs) using flexible poly (ethylene glycol) units as solvent reaction crosslinker, acrylated β-cyclodextrin as functional monomer, MAA as common functional monomer, and bisphenol A (BPA) as template.The flexible poly (ethylene glycol) unit chain not only endows the S-MIPs with solvent response function, but also increases the hydrophilicity of the material, so that the S-MIPs can selectively bond BPA in an aqueous medium through host-guest and hydrogen bonding. The selective extraction and detection of BPA in human urine was realized by combining DSPE and HPLC-DAD[43]. Tang et al. Established a method for the selective detection of alkaloids in plant extracts by heat-assisted DSPE combined with HPLC-UV using hydrophilic thermoresponsive molecularly imprinted resin (MIR)[44]. The method has low LOD, high recovery and good precision. Abbasi et al. Synthesized a hydrophilic magnetic molecularly imprinted biopolymer as an eco-friendly biosorbent, which combined with DSPE to achieve the selective extraction of cardiovascular drugs from human urine[45]. Benefiting from the hydrophilicity of MIP and the biodegradability of biosurfactant, this method is environmentally friendly, in line with the current development trend of green chemistry, and has high recovery rate and low interference, which is suitable for the selective extraction of clinical cardiovascular drugs. Li et al. Prepared a novel imprinted nanomaterial (RAM-MIPs) by reversible addition-fragmentation chain transfer polymerization (RAFTPP), which has the advantages of simple preparation conditions, uniform and controllable thickness of imprinting layer, fast adsorption, large binding capacity and good regeneration performance compared with other materials[46]. The combination of DSPE and HPLC-UV first achieved efficient separation, enrichment and detection of fluoroquinolones (FQs) in untreated milk and river water with low LOD (0.93~3.15μg·L-1), high recovery (80.7% – 105.9%) and RSD below 4.7%. Similarly, Xiong et al. Used the RAFTPP strategy to prepare a magnetic hydrophilic imprinting material (MIM) with multiple stimulus responses for selective extraction of BPA. MIM was used as a DSPE adsorbent and combined with HPLC-DAD to determine BPA in beverages. The recovery rate reached 80.7% ~ 108.2%, RSD < 6.1%, and LOD was as low as 3.75 nmol·L-1[47]. MIM exhibits significant adsorption capacity in aqueous solution, fast binding kinetics, excellent selectivity, sensitivity to multiple stimuli, and significant resistance to complex matrix interference. The intelligent MIM has a switchable function, which provides a convenient, economical and environmentally friendly scheme for further application in the enrichment, separation and detection of BPA in complex samples. Gholami et al. Prepared novel hollow porous molecularly imprinted nanospheres (HP-MINs) with good water compatibility by sol-gel method, and combined with DSPE to achieve specific recognition and extraction of blood pressure regulating drugs valsartan and losartan[48]. The hollow structure of HP-MINs not only has high affinity, fast adsorption kinetics and significant specificity, but also has high affinity for polar analytes due to its inherent hydrophilicity, and has high applicability in aqueous solution. Therefore, the established HP-MINs-DSPE-HPLC-UV showed good linearity for both valsartan and losartan in the concentration range of 5~2000μg·L-1 with low LOD (1.5μg·L-1 and 1.4μg·L-1). Yu et al. Established a rapid, simple, cheap, effective, stable and safe (QuEChERs) method for the determination of triazine herbicide residues in bivalves (mussels, scallops, oysters)[49]. In the DSPE process, MIPs as selective purification materials improved the removal rate of pigment interferents. The MIP-DSPE-GC-MS/MS method has good linearity, high sensitivity and precision, and can be used as an effective tool for monitoring the environmental pollution of triazine herbicides on aquaculture products and the health risk of consumers, assessing the risk of adults and children exposed to aquatic products residues in China, and providing valuable information for the safe consumption of aquatic products.
With the continuous development of nanotechnology in recent years, the advantages of large surface area to volume ratio of nanomaterials combined with the characteristics of DSPE without column loading and activation make the application scope of DSPE expand[40]. However, DSPE requires centrifugation and filtration, which still requires a lot of time and labor. In addition, direct dispersion and contact with complex actual samples can easily lead to the blockage of adsorbent action sites.

2.3 Magnetic solid phase extraction

Different from SPE and DSPE, magnetic solid phase extraction (MSPE) can quickly separate the adsorbent from the sample solution under the action of an external magnetic field, which not only combines the advantages of traditional packed solid phase extraction technology, but also avoids the time-consuming processes of solid phase extraction column packing, sample loading, activation, filtration, centrifugal separation and so on[50,51]. Therefore, MSPE has the advantages of simplicity, convenience, environmental protection and time saving, and can realize the integration of enrichment and separation. It is very suitable for rapid and efficient extraction of target compounds from bulk samples and rapid recovery of adsorbents. The schematic diagram of magnetic MIPs combined with MSPE is shown in Figure 4[52,53].
Ji et al. Established a method for selective enrichment of chloroacetamide herbicides in environmental water samples by amphiphilic magnetic MIPs[54]. Under the action of external magnetic field, the MSPE process can treat 150 mL of environmental water sample in 22 min. The method is rapid and convenient, and has low detection limit and quantification limit, which is expected to be widely used in the analysis of trace chloroacetamide herbicides in environmental water samples. Zhang et al. Used a one-step swelling method to prepare a novel magnetic restricted-access molecularly imprinted polymer (RAM-MMIP)[55]. Combining RAM-MMIP with MSPE and HPLC-UV, the rapid and effective separation of thienamycin in milk and river water samples was achieved. The established method has good linearity, the (R2>0.9977),LOD is as low as 10.4μg·L-1, the recovery rate is as high as 96. 5% ~ 101.1%, and the RSD is as low as 2. 8% ~ 3.8%. The material has the advantages of simple preparation conditions, high adsorption speed and large adsorption capacity, and has broad application prospects in the detection and separation of thienamycin in complex samples. Gao Ruixia et al. Constructed a series of hydrophilic or water-compatible magnetic MIPs, and studied their practical applications in detail, such as using carboxyl-functionalized magnetic nanospheres as carriers, estradiol as template molecules, and aniline as functional monomers to prepare core-shell estradiol magnetic MIPs[52,56]. The MIPs have good selective adsorption capacity and show potential application value for the accurate detection of estradiol in environmental water[57]. Furthermore, they used dopamine and polyethyleneimine as bifunctional monomers to synthesize hydrophilic magnetic MIP in aqueous solvent by layer-by-layer assembly, which can selectively separate luteolin from agricultural waste honeysuckle leaves[58].
For the application of aqueous phase recognition MIPs in sample pretreatment, our research group also carried out a series of studies, such as reporting a method of traditional MIPs combined with MSPE-HPLC-MS/MS for the detection of six triazine herbicides in environmental water samples[59]. In this method, MIPs were directly dispersed into environmental water samples, and the selective extraction of six triazine herbicides in 500 mL environmental water could be completed within 15 min, with matrix effect as low as 0.7% ~ 12.4%. Magnetic superhydrophilic molecularly imprinted resins (MMIRs) were innovatively prepared by one-pot condensation of amino-functionalized magnetic nanoparticles, resorcinol, melamine and formaldehyde. The established MMIRs-MSPE-HPLC-MS/MS method was used to detect triazine herbicides in aqueous medium samples, with LOD as low as 0.02~0.07μg·L-1, recovery as high as 85% ~ 101%, and RSD ≤ 7%[60]. Furthermore, formaldehyde, resorcinol and melamine are used as raw materials, and the surface imprinting technology is combined to construct the magnetic super-hydrophilic imprinted nano composite resin on the surface of the magnetic multi-walled carbon nanotube by one-step condensation.Combined with HPLC-MS/MS, the triazine herbicides in environmental water samples were efficiently enriched and determined. The method had good linearity, low (R2≥0.9987),LOD (0.007~0.068μg·L-1) and good precision (RSD < 9%)[61]. Recently, hydrophilic MMIRs with elevated adsorption and recognition properties were prepared using a two-step template immobilization strategy combined with a surface imprinting technique[62]. This MMIR was used as an MSPE adsorbent in combination with HPLC-UV to achieve the targeted separation and detection of trace chlorophenols in complex environmental water samples, and the method exhibited low LODs(0.056~0.102μg·L-1), high recovery (91% – 100%), wide linear range (0.5~100μg·L-1,R2≥0.991), and good precision for five chlorophenols. This study provides a new perspective for the development of superior hydrophilic molecularly imprinted composites and the establishment of more effective sample separation techniques for the control/monitoring/detection of target pollutants in complex aqueous environments.

2.4 Solid phase microextraction

Solid-phase microextraction (SPME) is a sample pretreatment technology that integrates sampling, extraction, preconcentration and sample injection. The key of SPME technology is to coat a small amount of extraction phase on a solid support to form various extraction devices, including fibers, stirrers, vessel walls, tubes, and disks[63⇓~65]. SPME coatings have been widely used in the analysis of food, environmental, pharmaceutical and biological samples due to their solvent-free, miniaturization, portability and automation. The combination of SPME coatings with MIPs will promote the complementary advantages of the two materials, and the combination with hydrophilic or water-compatible MIPs will further broaden their applications[63,64]. Li et al. Coated a water-compatible molecularly imprinted layer on fused silica to construct a water-compatible molecularly imprinted fiber for solid-phase microextraction of four organophosphorus pesticides in fruits[66]. In this study, the established method was compared with LLE and other SPME-based methods, and it was found that the water-soluble MIP-SPME had better detection limits and recoveries, which confirmed the advantages of this method in the analysis of organophosphorus in complex aqueous solutions. Li et al. Used chitosan to synthesize a novel hydrophilic molecularly imprinted material (HMICS), which was combined with SPME technique for selective enrichment of gallic acid in red ginseng tea[67]. Response surface methodology (RSM) was used to optimize the extraction process, and the optimal extraction amount was 8.57 mg·g-1, the extraction time was 30 min, and the solid-liquid ratio was 20 mg·mL-1. Compared with the traditional method, this method has the advantages of simple operation, high recovery and selectivity, good repeatability, and low sample and reagent consumption, which is expected to promote the rapid development and wide application of molecular imprinting technology combined with SPME. Furthermore, they prepared a new hydrophilic molecularly imprinted chitosan microsphere (MICSM-MGO) on the surface of magnetic graphene oxide with hydrophilic eutectic solvent (DES) as functional monomer and used it for chlorophenol pollutants in SPME environmental water. The MICSM-MGO-SPME method can be used for the sensitive and accurate determination of trace chlorophenols in water samples because of its good selective extraction ability and excellent reusability[68]. Lu et al. Prepared a novel hydrophilic tetracycline-imprinted SPME fiber by silanization on the surface of stainless steel wire using an improved multiple copolymerization method, and used it to extract tetracyclines from animal-derived foods (chicken, fish, and milk)[69]. Under the optimized SMPE conditions, all tetracyclines showed good linearity in the range of 5~1000μg·L-1 with LOD as low as 0.38~0.72μg·kg-1, and the recovery reached 77.3% – 104.4%. The MIP-coated fiber has high thermal and chemical stability, which improves the extraction efficiency and the selectivity of target molecules in water matrix.
At present, the development of SPME technology has benefited the research in various fields. The technology is convenient for field sampling and sample preparation, can realize operation automation, and is also convenient for remote monitoring. Combined with water phase identification MIPs, it will further expand its application scope. However, due to its low consumption of solvent and materials, SPME is more suitable for the analysis of small amounts or small volumes of samples, and its preparation cost is high and its fibers are fragile[70].

2.5 Tip solid phase extraction

PT-SPE is a green micro-solid phase microextraction technology, which has the advantages of small adsorbent dosage, low solvent consumption, strong versatility, simple operation, low cost and easy automation[71,72]. Arabi et al. Developed a pipette tip extraction method for the analysis of prednisolone in urine samples using hydrophilic nano-MIP[73]. Compared with the traditional SPE method, the extraction column can be constructed by filling 10. 0 mg of hydrophilic MIP into a 100 μL pipette, which is simple, rapid, low-cost and low consumption of toxic solvents. Yan Hongyuan et al. Of Hebei University established a green micro-solid phase extraction method for the analysis of four plant growth regulators in fresh coconut juice by using 5 mg hydrophilic melamine-urea-formaldehyde MIRs as adsorbent, 100 μL micro-pipette tip as column, and HPLC-FD as detector[74]. The whole MIR-mini-SPE process is simple, efficient, and does not consume organic solvents. They also constructed a hydrophilic MIRs micro-solid phase extraction device by growing a melamine-urea-formaldehyde MIRs monolithic column in situ at the end of a pipette and used it for the analysis of plant growth regulators in aqueous matrices[75]. Furthermore, they constructed another micro-solid phase extraction device with 5 mg hydrophilic glyoxal urea formaldehyde MIRs as adsorbent for the selective separation of three organochlorine pesticides in spinach[76]. The above method integrates the advantages of hydrophilic MIRs and tip solid phase extraction, and excellent selective analysis results are obtained, which broadens the application prospect of aqueous recognition MIPs in the analysis of trace analytes in water matrix. In addition, Wu et al. Prepared 2,4-dichlorophenoxyacetic acid (2,4-D) MIP, and constructed a low back pressure monolithic column PT-SPE device to achieve efficient enrichment of 2,4-D in water samples[77]. PT-SPE avoids the problems of irregular packing in adsorbent packed columns and high back pressure and low flux in the bulk polymer at the tip. The device for extracting 2,4-D from lake water has high recovery rate, high enrichment coefficient and good selectivity.
Although PT-SPE has many advantages over conventional SPE, it still has some disadvantages, such as easy clogging of microtubules, easy leakage of adsorbents, and difficult compatibility with solid samples. As one of the micro-solid phase extraction, PT-SPE is also suitable for the analysis of small amounts or small volumes of samples.

2.6 Stir bar sorptive extraction

Stir bar sorptive extraction (SBSE) is an environmentally friendly microextraction technique, which is derived from SPME. However, SBSE is 50 to 250 times larger than SPME, and has higher sample capacity and absolute recovery. SBSE has been developed for more than 20 years. As an efficient sample pretreatment technique, SBSE has been widely used in environmental, food and biological analysis[78][79]. Hasan et al. Reviewed the research progress of SBSE hydrophilic adsorption materials in recent years, especially the preparation of new selective SBSE coatings[80]. For example, the development of new coatings using nanoparticles and composites, the improvement of existing coating methods or the introduction of new coating technologies, such as chemical attachment, molecular imprinting, new sol-gel methods, bulk coating, solvent exchange chemistry, etc. Fan et al. Constructed a water-compatible graphene oxide/MIP-coated stir bar coupled with HPLC-UV for selective detection of propranolol in urine samples[78]. The hydrophilic blotting layer grown in situ on the surface of the stirring bar is beneficial to the repeated selective adsorption-desorption equilibrium of propranolol in aqueous matrix. Therefore, the established SBSE-HPLC-UV method has good water compatibility, specificity, and excellent analytical performance. In another work, Gomez-Caballero et al. Designed stir bars with in situ grown water-compatible MIP coatings for selective adsorption of glyphosate herbicides in water and soil samples[81]. Benefiting from the water compatibility and selectivity of the stir bar, the constructed method has less matrix effect in aqueous samples, and can be used not only for the detection of water samples, but also for the analysis of other aqueous extraction media such as soil or food. Recently, Yao et al. Used paraquat (PQ) as a template and monohydroxyurea (OH) Q [7] as a monomer to form a one-dimensional self-assembled inclusion complex by the inclusion of (OH) Q [7] cavity to PQ, and further obtained a MIP stir bar (MIP-SB) coating with complementary shape, size and functional group to the target analyte PQ by sol-gel technology[82]. The molecularly imprinted coating has specific adsorption for cationic PQ in aqueous medium, and has no obvious adsorption effect on other quaternary ammonium compounds with similar structures, such as ethyl viologen, diphenyl, diphenyl azaquine, and the like. Trace PQ in environmental water and vegetable samples was determined by MIP-SB combined with HPLC-UV. The established MIP-SBSE-HPLC-UV method has a wide linear range of 100~10 000 ng·L-1, the LOD of water samples is as low as 8.2 ng·L-1, the LOD of vegetable samples is as low as 0.02~0.85 mg·kg-1, the recovery rate is 70. 0% ~ 96.1%, and the RSD is less than 7. 6%, which is very suitable for the determination of trace PQ in complex matrices.
Although SBSE is easy to operate and has a high enrichment factor, the stir bar fabrication process is complex, time-consuming, and fragile, and the stir bar coating is prone to clogging and difficult to be compatible with solid samples.

2.7 Membrane protected solid phase extraction

Membrane protected solid phase extraction (MPSPE) is a method in which the adsorbent is pre-packaged in a porous membrane, and the analyte can be adsorbed and desorbed through the porous membrane and transferred to the adsorbent. The MPSPE process is shown in Figure 5[83,84]. MPSPE is particularly suitable for the enrichment of targets in complex samples, because the porous membrane can effectively prevent large particles, proteins, humus and other substances from approaching the imprinting cavity, which can significantly reduce the matrix effect[85]. Our research group prepared spherical MIPs by emulsion polymerization, and encapsulated the MIPs in polypropylene microporous membrane to make MIPs adsorption package, which was used to directly and selectively extract triazine herbicides from unconcentrated and unfiltered tea extract[86]. Benefiting from the double promotion of MPSPE and MIPs against matrix interference, the established MIPs-MPSPE-HPLC-MS/MS method has a good linear relationship in the range of 0.5~250 ng·g-1 with (R2≥0.9992),LOD as low as 0.09~0.18 ng·g-1 and a high recovery rate (81% – 104%). The molecularly imprinted material-based membrane-protected solid phase extraction method is expected to be widely used for the enrichment of triazine herbicides in complex samples. Similarly, S Sánchez-Gonz González et al. Prepared a series of MIPs using synthetic cannabinoids, ethanone, and 3-methylmethcathinone as templates, EGDMA as a functional monomer, and divinylbenzene as a crosslinking agent[87,88]. DSPE-HPLC-MS/MS coupled with porous membrane protection achieved excellent analytical performance for the separation of cathinones and synthetic cannabinoids from complex matrices. These methods will provide reliable results when applied to the analysis of urine samples from drug abusers (cathinones and cannabinoids). In addition, the method is also applicable to the targeted analysis of targets in other biological fluids, such as serum, blood and oral liquid, and has wide application potential in forensic identification and other fields. Different from the traditional polymer membrane to construct MIP adsorption package, Muhammad et al. Constructed a membrane-protected MIP microextraction rod by filling MIP particles in polypropylene hollow fibers[89]. This method overcomes the problem of insufficient recognition ability of MIP in aqueous solution, and integrates SPE, liquid phase microextraction and membrane protected solid phase extraction in one step. The established method combined with HPLC-FD was used to extract and determine indole-3-butyric acid in mung bean sprouts. The method has good linearity, the correlation coefficient is 0.9999, the LOD is as low as 0.075 mg·kg-1, and the recovery rate is as high as 88.9% ~ 106.4%.
Although the protective effect of the membrane can effectively prevent the imprinting site from being blocked and further improve the anti-matrix interference ability of the method, the operation of MPSPE is more complex and the construction process is cumbersome.There are few application examples of MPSPE combined with aqueous phase to identify MIPs, but thanks to its strong ability to resist matrix interference, MPSPE combined with MIPs has significant advantages in the analysis of trace targets in undiluted and untreated complex real samples.
Table 2 summarizes the advantages and disadvantages of various pretreatment methods.

3 Conclusion and prospect

In this paper, the application of various sample pretreatment techniques combined with aqueous phase recognition MIPs in the analysis of aqueous samples is discussed in detail from the perspective of sample pretreatment techniques. Although many researchers have made great efforts and made many breakthroughs in this direction, this problem continues to face arduous challenges due to various complex factors affecting the aqueous phase recognition of MIPs and the complexity of the sample matrix. Therefore, future research on the application of aqueous phase recognition MIPs in sample pretreatment can focus on the following two aspects:
In the construction of aqueous recognition MIPs: (1) The types of hydrophilic crosslinking agents and hydrophilic functional monomers are still very limited, which are far from meeting the imprinting needs of a wide variety of target molecules. In recent years, hydrophilic monomers and crosslinking agents based on non-free radical polymerization will continue to be developed, and the relatively mature imprinting technology based on free radical polymerization will be further developed; (2) Many factors in the construction process of aqueous recognition MIPs will affect the recognition effect (such as pH, feeding ratio, polarity of porogen, etc.). If the combined molecular imprinting technology, theoretical calculation or computational simulation and other auxiliary means are applied to the construction process, it will be of great significance to the development of universal methods for aqueous recognition MIPs; (3) The mechanism of imprinting and recognition process is still not mature enough. If combined with in-situ monitoring and real-time monitoring technology, it will play an important guiding role in further clarifying the mechanism in this field and accurately customizing the target aqueous phase recognition MIPs.
In terms of sample pretreatment: (1) develop miniaturized, green, automated and intelligent sample pretreatment technologies, such as microextraction devices or technologies with low consumption of adsorbents/reagents/solvents/samples, to achieve economical, labor-saving, portable and rapid sample analysis; (2) Develop an economical, environmentally friendly and less harmful extraction process; (3) Develop automation equipment and devices to achieve high throughput, unattended and unmanned operation, low labor intensity and low manpower consumption, and to obtain reproducible and repeatable data. (4) Obtain intelligent algorithms or responses based on powerful computational tools or artificial intelligence for automatic recognition and evaluation of detection results.

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Funding

National Natural Science Foundation of China(22004047)

National Natural Science Foundation of China(21906062)

Project of Department of Science & Technology of Jilin Province(20180623042TC)

Project of Human Resources and Social Security Department of Jilin Province(2017956)

Project of Ecological Environment Department of Jilin Province(2019-01-07)

Project of Jilin Province Development and Reform Commission(2021C036-7)

Project of Education Department of Jilin Province(JJKH20200427KJ)

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