RNA nucleoside recognition by phthalocyanine-based molecularly imprinted polymers

Highly selective molecularly imprinted polymers (MIPs) having a phthalocyanine-based recognition centre as receptors for RNA nucleoside were prepared. In particular, a zinc phthalocyanine peripherally substituted with methacrylic groups was synthesized and utilized as functional monomer in combination with methacrylic acid (MAA) to form polymers with the aim to obtain MIPs having improved binding capacity and selectivity for nucleosides. Tri-O-acetyladenosine (TOAA) was utilized as model template in the preparation of the MIPs. The corresponding non metallated phthalocyanine was also prepared and used as functional monomer for the preparation of the MIPs in order to understand the role of the Zinc(II) ion in the binding capacity of the polymers towards the template molecule. The MIP prepared by using both the zinc phthalocyanine and MAA showed higher binding ability towards TOAA compared to the MIPs prepared using only MAA or its combination with the non metallated phthalocyanine. The results obtained suggest that the nucleoside is specifically bound to the polymer through multi-point interactions involving both the coordination of the nucleoside to the metal of the phthalocyanine and hydrogen bonding/electrostatic interactions with MAA and the modifiers linked to the phthalocyanines. As for the selectivity, the MIPs exhibited relative high binding affinities for TOAA while they did not show any binding capacity for the other RNA nucleosides.     

Grafting of molecularly imprinted polymers from the surface of Fe3O4 nanoparticles containing double bond via suspension polymerization in aqueous environment: A selective sorbent for theophylline

Molecularly imprinted polymers (MIPs) were grafted from the surface of Fe₃O₄ nanoparticles containing double bond via suspension polymerization in aqueous environment, and the leakage of Fe₃O₄ nanoparticles from MIPs was overcome in this study. The effect of different cross‐linker on adsorption capacity of the resultant magnetic MIPs was investigated using pure trimethylolpropane trimethacrylate (TRIM) or the mixture of TRIM and divinylbenzene (DVB) as cross‐linker. Both magnetic MIPs exhibited higher adsorption capacity for the template theophylline than the corresponding non‐imprinted polymer, and Freundlich model fitted reasonably well for theophylline adsorption on both magnetic MIPs. In addition, both magnetic MIPs exhibited good recognition properties for the template theophylline versus caffeine, and the selectivity of magnetic MIPs using pure TRIM as cross‐linker (mag‐MIP‐TRIM) was much higher than those using the mixture of TRIM and DVB as cross‐linker (mag‐MIP‐TRIM and DVB). The adsorption dynamics of theophylline on both magnetic MIPs fitted well with the first‐order kinetic model, but the adsorption equilibrium on mag‐MIP‐TRIM and DVB reached faster than that on mag‐MIP‐TRIM. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

甲基对硫磷分子印迹聚合物制备中溶剂和功能单体的影响

为了有效的分离富集水样中的有机磷农药,以甲基对硫磷为模板、二甲基丙烯酸乙二酯为交联剂,采用传统方法制备了甲基对硫磷分子印迹聚合物(MIPs).考察了三种溶剂和三种功能单体及其用量对MIPs吸附性能的影响.结果表明,以氯仿为溶剂制得的MIP特异性最强,溶剂用量对MIPs比表面积和溶胀比的影响显著.氯仿用量为35 mL时MIP性能最理想;~1H-NMR研究显示,4-乙烯基吡啶(4VP)与模板分子通过π-π堆积作用形成稳定的复合物,按4VP与模板分子摩尔比4:1制得的MIP特异性和亲和性较理想.测定了该MIP的吸附等温线,利用Langmuir等温式分析结果,得出其饱和吸附量为625.5 μmol·g~(-1),明显高于非印迹聚合物的饱和吸附量285.7 μmol·g~(-1).利用该MIP对模拟海水样品进行研究,结果显示,MIP对不同有机磷农药的吸附能力表现出一定的差异.通过进一步优化,提高MIPs的选择性,该材料有望用于水样中甲基对硫磷的分离富集和分析.     

D-对羟基苯甘氨酸分子印迹聚合物的制备及分子识别能力

以D-对羟基苯甘氨酸（D-HPG）为模板分子,以丙烯酰胺（AM）和α-甲基丙烯酸（MAA）为功能单体,乙二醇二甲基丙烯酸酯为交联剂,合成了D-HPG分子印迹聚合物,并测定其对D-HPG的识别能力。静态吸附实验表明,以MAA为功能单体制备的分子印迹聚合物具有更强的分子识别能力,其饱和吸附量达43.9 μmol•g^-1,印迹因子α为3.6。分子力学计算表明,MAA与D-HPG形成复合物的结合能较大,且MAA在乙醇和水中的溶剂化能较小,因此与AM比较,MAA和模板分子D-HPG在乙醇和水中能形成更加稳定的复合物。紫外光谱分析表明,MAA与D-HPG之间的结合力比AM与D-HPG之间的结合力要强,与分子力学计算以及静态吸附实验得到的结果相一致。     

The use of metal‐containing monomer in the preparation of molecularly imprinted polymer to increase the adsorption capacity

Molecular imprinting is an elegant approach to induce antibody like recognition ability in synthetic polymers. The technique of molecular imprinting has been used extensively in the preparation of tailor‐made stationary phases in chromatography, sorbents in solid phase extraction, sensor elements, etc. Though several of the reported molecularly imprinted polymers (MIPs) possess substrate selectivity comparable to antibodies, they are poor in adsorption capacity. The adsorption capacity could be improved presumably through enhanced interaction between the functionalities of the monomers and the print molecule. A simple approach to improve the interaction is perhaps the use of chemically modified monomers in the synthesis of the MIPs. This article explores this possibility by using a metal‐containing monomer in the synthesis of MIP. The data obtained using a copper acrylate based MIP and cholesterol as substrate indicates the adsorption capacity can be improved considerably through the simple chemical modification of the functional monomer. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 2795–2799, 2001     

Polyamide film containing a molecularly imprinted polymer prepared on a paper surface by interfacial polymerization and its selective adsorption of benzalkonium chloride

In this study, paper coated with a polyamide film containing a molecularly imprinted polymer (MIP) of benzalkonium chloride (BKC) is prepared. Its BKC adsorption ability and selectivity for BKC adsorption are investigated. The MIP is prepared by agitating an ethylenediamine solution containing an azo initiator, BKC as a template material, and methacrylic acid (MAA) as the functional monomer. First, filter paper soaked in this mixture is impregnated with a cyclohexane solution of terephthaloyl chloride and a BKC–MAA–MIP-containing polyamide film is prepared on the surface of the paper. Paper containing BKC–MAA–MIP adsorbs BKC. The paper with the highest BKC removal efficiency is prepared under the following conditions: 4 mL MAA functional monomer, 2.5 w/v% ethylenediamine, and 10 min MIP synthesis time. The paper with BKC–MAA–MIP selectively adsorbs BKC from a solution containing BKC, tetracycline hydrochloride, and caffeine. Thus, a polyamide film containing BKC-MAA-MIP formed on paper can effectively and selectively remove BKC from aqueous environments.     

Preparation of molecularly imprinted polymers: Diethyl(3‐methylureido)(phenyl)methylphosphonate as a dummy template for the recognition of its organophosphate pesticide analogs

A novel compound, diethyl(3‐methylureido)(phenyl)methylphosphonate (DEP), possessing an organophosphate skeleton, was synthesized and used as a dummy template to prepare molecularly imprinted polymers (MIPs) for the recognition of organophosphate pesticide analogs. Computational modeling was used to study the primary intermolecular interactions in the prepolymerization mixture. It was found that the interaction force between DEP and the monomers was hydrogen bonding. A series of MIPs were synthesized with different monomers and were evaluated by adsorption experiments, which showed that methacrylic acid was used as an appropriate monomer and a molar ratio of DEP to MAA of 1 : 9 was optimal. Scatchard analysis showed that there might have been two types of binding sites in the MIPs. DEP and several pesticides were used in molecular recognition specificity tests of DEP–MIP, which exhibited better selectivity and reservation ability for organophosphate pesticides, such as methamidophos and orthene, possessing amino or imino groups and a smaller steric hindrance. On the basis of the use of a dummy molecule as template, the problem of template leakage could be avoided; this, thereby, improved the specificity of analysis. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

单体对分子印迹聚合物分子识别能力的影响：量子化学计算与实验研究

采用密度泛函方法计算功能单体与印迹分子的结合能,以与目标分子结合能最大的单体分子来合成分子印迹聚合物.为此,以茶碱为印迹分子,氯仿为溶剂,首先计算了茶碱与甲基丙烯酸、丙烯酰胺和三氟甲基丙烯酸的结合能,其强度顺序为：三氟甲基丙烯酸 > 甲基丙烯酸 > 丙烯酰胺.然后以茶碱为印迹分子、氯仿为溶剂、二甲基丙烯酸乙二醇酯为交联剂,分别采用上述3种单体合成分子印迹聚合物并测定了其分子识别能力,实验结果和量子化学计算结果具有一致性.最后,采用1H NMR考察了茶碱和上述3种单体之间的氢键作用,揭示出二者相互作用的内在机制.研究结果表明量子计算方法可以应用于合成分子印迹聚合物时单体的选择.     

Synthesis and characterization of high selective molecularly imprinted polymers for bisphenol A and 2,4-dichlorophenoxyacetic acid by using supercritical fluid technology

Molecularly imprinted polymers (MIPs) have been extensively used in chemical and biochemical related areas due to their high molecular recognition affinity and selectivity for the target molecule. On the other hand, supercritical polymerization is relatively novel technique, which can be applied in the polymerization without hazard organic solvent. This work introduces a supercritical fluid polymerization technique for preparation of MIP particles. The adsorption properties of prepared MIP particles are also investigated. The MIPs were prepared with methyl methacrylate (MMA) as a third monomer, methacrylic acid (MAA) as a functional monomer, templates (bisphenol A (BPA) and 2,4-dichlorophenoxyacetic acid (2,4-D)), methyl methacrylate (MMA) as a third vinyl monomer and ethylene glycol dimethacrylate (EGDMA) as a cross-linker. Equilibrium binding experiments are conducted to evaluate the binding characteristics of MIPs and templates (BPA and 2,4-D). The Scatchard plot analysis demonstrates that two classes of binding sites are formed with the equilibrium dissociation constants. The adsorption ability of the MIPs was also evaluated by measuring the adsorbed amounts of a similar imprinted template structure, the selectivity factor (α), and the imprinting-induced promotion of binding (IPB).     

溶剂对分子印迹聚合物分子识别能力的影响：实验研究与计算量子化学分析

以茶碱为印迹分子，甲基丙烯酸为功能单体，二甲基丙烯酸乙二醇酯为交联剂，以氯仿、二甲基亚砜和四氢呋喃为溶剂，合成了分子印迹聚合物并测定了其对茶碱分子的识别能力，实验结果显示，在氯仿中合成的MIPs的分子识别性能最佳.综合Scatchard分析吸附行为、¹H NMR测定氢键以及量子化学中的密度泛函计算印迹分子和单体分子的溶剂化能等方法，研究聚合反应的溶剂体系对于印迹聚合物分子识别能力的影响及其作用机制.计算结果显示：采用与印迹分子和单体相互作用力较弱的溶剂体系所合成的印迹聚合物具有较高的分子识别性能.这与¹H NMR分析结果和吸附测定实验结果具有一致性.上述结果表明，溶剂对于分子印迹聚合物的分子识别性能具有重要的影响，而计算量子化学分析对于分子印迹介质合成时的溶剂体系选取和优化具有很好的指导作用.     

Comonomer effects on binding performances and morphology of acrylate-based imprinted polymers

The objective of this study was to investigate the effect of different functional groups of molecularly imprinted polymers (MIPs) on the binding characteristics towards a specific template molecule by examining selectivity and recognition processes. Several non-covalent theophylline imprinted polymers (TIPs) were prepared by using only methacrylic acid (MAA), or MAA and 2-hydroxyethyl methacrylate (HEMA) comonomer, or MAA and acrylamide (ACM) comonomer. In all cases, a high amount of ethylene glycol dimethacrylate (EDMA) as crosslinker existed in the medium. The highest selective theophylline binding of TIPs was found to be 61%, 41% and 40% for MAA/EDMA, MAA/HEMA/EDMA and MAA/ACM/EDMA systems, respectively. The use of a comonomer (ACM or HEMA) reduced the binding performance of the MAA/EDMA polymer matrix, probably due to the monomer-monomer association and morphological differences. Results obtained from the batch binding experiments demonstrated that all of the TIPs have sites that have selective binding ability for theophylline, but not to another structurally similar molecule, caffeine. According to the Langmuir isotherm model, a heterogeneous distribution of binding sites was observed in the polymers. The maximum association constant and binding site density were computed as 2.3 × 10² mM⁻¹ and 8.6 μmol/g, respectively, for copolymer of MAA/EDMA under the examined concentration range.     

三硝基甲苯分子印迹电化学传感器的制备和应用

以三硝基甲苯（TNT）为模板分子，甲基丙烯酸（MAA）为功能单体，采用乳液聚合法制备TNT的分子印迹聚合物（MIPs）。将制备的MIPs分散在溶剂中，通过表面涂覆法制备出检测TNT的分子印迹电化学传感器。紫外光谱表明TNT与MAA之间存在相互作用力，有助于形成结构稳定、亲和性强的MIPs。利用扫描电镜观测不同制备条件下印迹聚合物的表观形貌，发现溶剂用量为30mL、乳化剂用量为12mg时制备的聚合物形貌较优异。吸附实验表明MIPs对TNT的吸附量随着TNT初始浓度的增加而增加，140min后达到最大吸附量的95%。MIPs对TNT的分离常数远大于RDX和DNT，对RDX和DNT的选择性系数均达到4.4以上，说明MIPs对TNT有较好的选择性吸附能力。铁氰化钾探针实验和对TNT的响应曲线验证了电化学传感器的成功制备，该传感器富集3min就达到了最大电流值的94%，5min内达到吸附平衡。TNT浓度在0.1~5mg/mL的范围内与峰电流有良好的线性关系，检出限为0.06mg/mL。MIPs传感器对TNT的电流响应分别为DNT和RDX的3.13倍、3.27倍，说明其对TNT分子具有很强的特异性识别能力。     

Optimal design of an imprinted preassembled system by quantum chemical calculations and preparation of a surface‐imprinted material for the selective removal of quinoline

In this study, we examined the rational preparation of molecularly imprinted polymers (MIPs) for the selective removal of quinoline from octane. Before the preparation, density functional theory, as one of the methods of quantum chemical calculation, was used for the simulation of a quinoline‐imprinted preassembly system. Methacrylic acid turned out to be the more suitable monomer for quinoline compared with acrylamide, and different template–monomer ratios, including 1:1, 1:2, and 1:3, were studied and are discussed. On the basis of the result of molecular simulation, quinoline‐imprinted polymers were prepared with a combination of surface imprinting and living polymerization. The prepared quinoline–MIPs were characterized and used as selective adsorbents for batch‐mode binding experiments. The fitting result of the adsorption data indicates that the adsorption kinetics and adsorption isotherms of the quinoline‐imprinted polymers fit well a pseudo‐second‐order kinetics model and the Freundlich model, respectively. A selective recognition ability was demonstrated by equilibrium binding analysis. This study will provide needful guidance and a theoretical basis for the preparation of imprinted materials in the field of industrial denitrification. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 41730.     

Preparation and evaluation of a molecularly imprinted polymer for tolazoline

A uniformly sized molecularly imprinted polymer for the peripheral vasodilator drug tolazoline (T‐MIP) was prepared, and a nonimprinted polymer (NIP) was also synthesized in the same way but in the absence of the template. The T‐MIP was prepared with methylacrylic acid as functional monomer and ethylene glycol dimethacrylate as crosslinker by a multistep swelling and polymerization method. These imprinted materials were characterized by scanning electron microscopy, nitrogen adsorption, and static adsorption experiments. Binding studies were also performed to evaluate the uptake of T‐MIP and NIP with the results that T‐MIP had a significantly higher binding capacity for tolazoline (T) than did NIP. The maximum static adsorption capacities of T‐MIP and NIP for T were 78.9 and 38.8 μmol/g, respectively. The T‐MIPs and NIPs were used as stationary phases of solid‐phase extraction (SPE), and a relative selectivity coefficient (k′) value of 5.21 was obtained, which showed that the T‐MIP sorbent had higher selectivity than the NIP sorbent. The method was applied to the determination of T in urine samples. The prepared polymer sorbent showed promise for SPE for gas chromatography determination of T in urine samples. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Designing and preparing of quercetin surface‐imprinted material and its molecular recognition characteristics

Quercetin is an important compound of flavonoids. In this work, quercetin molecule surface‐imprinted material with high performance was prepared using a novel surface‐imprinting technique of “synchronously graft‐polymerizing and imprinting.” The modified micron‐sized silica gel particles containing amino groups were used as matrix, methacrylic acid (MAA) was used as functional monomer, and N,N′‐Methylenebisacrylamide (MBA) was used as crosslinker. In dimethyl formamide solution of quercetin, MAA molecules arranged automatically around the template quercetin molecule by right of hydrogen bonding interactions of two type, ordinary hydrogen bond and π‐type hydrogen bond. By initiating the surface‐initiating system of – , the graft/cross‐linking polymerization of MAA on SiO₂ particles and the quercetin molecule surface‐imprinting were simultaneously carried out, forming quercetin molecule surface‐imprinted material MIP‐PMAA/SiO₂. With another two flavonoids, rutin and genistein, as contrasting substances, the molecule recognition character of the quercetin molecule surface‐imprinted material MIP‐PMAA/SiO₂ was investigated with batch and column methods. The experimental results show that the imprinted material MIP‐PMAA/SiO₂ possesses special recognition selectivity and excellent binding affinity for quercetin molecule. The binding capacity of MIP‐PMAA/SiO₂ for quercetin is 0.325 mmol/g, and its selectivity coefficients for quercetin relative to rutin and genistein are 7.69 and 4.40, respectively. The main conditions of imprinting process affect the property of MIP‐PMAA/SiO₂ greatly, and the optimal molar ratio of monomer MAA to crosslinker MBA is 7 : 1 and appropriate molar ratio of monomer MAA to template quercetin is equal to 6 : 1. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 41112.     

戊唑醇-三唑酮双模板分子印迹聚合物在烟叶农残检测中的应用

以戊唑醇（TBZ）和三唑酮（TDF）为双模板分子，甲基丙烯酸（MAA）为功能单体，乙二醇二甲基丙烯酸酯（EGDMA）为交联剂，按摩尔比为1∶4∶20制备了戊唑醇-三唑酮双模板分子印迹聚合物（MIPs）。考察了MIPs的吸附动力学、静态吸附及亲和位点特征和选择识别性能。结果表明，MIPs可在2.5h内达到吸附平衡，Scatchard分析得出MIPs存在高低两类亲和位点，且具有良好的组选择性和特异选择性。以MIPs作为固相萃取填料，制备分子印迹固相萃取柱（MISPE）用于烟叶样品前处理，并建立MISPE-超高效液相色谱-串联质谱法检测烟叶中（戊唑醇、三唑酮、腈菌唑和三唑醇）残留的方法。结果显示，MISPE柱对戊唑醇、三唑酮、腈菌唑和三唑醇的富集效果较好，平均回收率为72%~110.3%，相对标准偏差在2.38%~7.92%（n=3）。该方法简单、选择性高，可实现对烟叶中三唑类杀菌剂残留的准确分析。     

Preparation of (S)‐ibuprofen‐imprinted polymer and its molecular recognition study

Two molecularly imprinted polymers (MIPs) were prepared using (S)‐ibuprofen as the template molecule as well as methacrylic acid (MAA) or 4‐vinylpyridine and ethylene glycol dimethacrylate (EGDMA) as the functional monomer and crosslinker, respectively. Free radical polymerization was carried out at 4°C under ultraviolet (UV) radiation. The MIPs thus obtained were ground into 25–44 μm, which were slurry packed into analytical columns. The template molecules were removed by acetic acid/methanol solution (1:9, v/v). high‐performance liquid chromatography (HPLC), with UV detection, was used to evaluate the binding performance of the MIP for the template. The selectivity of (S)‐ibuprofen and naproxen on the host–guest system were assessed using acetonitrile‐based mobile phases. The limits of detection of ibuprofen and naproxen were found to be 0.1844 mmol/L and 0.3264 mmol/L, while the limits of quantitation were 0.6262 mmol/L and 1.0909 mmol/L, respectively. The stationary phase was applied successfully to the commercial tablet analysis. Ibuprofen and naproxen were extracted from tablets with acetonitrile; analysis results showed a good relative standard deviation (RSD) of 0.81–1.24% and accuracy from ?4.01 to +2.98% for ibuprofen as well as an RSD of 0.59–0.86% and accuracy from ?4.01 to ?2.01% for naproxen. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 2972–2979, 2006     

Imprinted β‐cyclodextrin polymers using naringin as template

The objective of this study was to identify a kind of molecular imprinting polymer (MIP) which was suitable for recognizing naringin (NG) in aqueous medium. Based on two crosslinkers (hexamethylene diisocyanate and epichlorohydrin) and two polymerization methods (solution polymerization and emulsion polymerization), four non‐covalent naringin‐β‐cyclodextrine (NG‐β‐CD) imprinted polymers were prepared by using β‐CD as a functional monomer and NG as a template molecule. The binding property and selectivity were evaluated by equilibrium binding experiments. These demonstrated that all the sites in the MIPs show good selective binding ability for NG from naringin dihydrochalcone, a structurally similar molecule. Of the four MIPs, rod‐like 3# MIP which was prepared by emulsion polymerization using hexamethylene diisocyanate as crosslinker exhibited the highest selectivity, its imprinting factor α being 1.53. Scatchard analysis of 3# MIP suggests that there are two classes of binding sites during the MIP's recognition of NG. Additionally, the 3# MIP could be used at least five times without any loss in sorption capacity. Copyright © 2011 Society of Chemical Industry     

Molecular imprinted solid‐phase extraction of huperzine A from Huperzia Serrata

On the basis of the non‐covalent interaction between template and monomer, porous molecularly imprinted polymers (MIPs) were synthesized by a thermal‐initiated polymerization method using huperzine A as template, acrylamide, or methacrylic acid as function monomer, ethylene glycol dimethacrylate as cross‐linking agent. The interaction between template and functional monomers was studied by UV spectrophotometry, which showed a formation of huperzine A‐monomer complexes with stoichiometric ratio of 1 : 2 in the pre‐polymerized systems. The resultant MIP particles were tested in the equilibrium binding experiment to analyze their adsorption ability to huperzine A, and were characterized by Fourier Transform Infrared (FTIR) study. The recognition properties of MIP were estimated in solid‐phase extraction by selecting four compounds (isolated from the Chinese herb Huperzia serrata) as substrates, and were compared with and prior to those of the NIP. High affinity and adsorption of MIP1 which was prepared in chloroform with huperzine A as imprinted molecule, and acrylamide (AM) as functional monomer, made an attractive application of MIP1 in separation processes. In final, using MIP1 solid‐phase extraction micro‐column, huperzine A was enriched and separated from the real extraction sample of Huperzia serrata. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Fabrication of ordered microporous styrene‐acrylonitrile copolymer blend imprinted membranes for selective adsorption of phenol from salicylic acid using breath figure method

Highly selective, ordered microporous molecularly imprinted membranes (MIMs) for phenol were synthesized by breath figure (BF) method using styrene‐acrylonitrile copolymer (SAN) as the membrane matrix and molecularly imprinted polymer nanoparticles (nano‐MIPs) as the imprinted nanoparticles. The nano‐MIPs were synthesized by oil‐in‐water emulsion polymerization using 4‐vinyl pyridine (4‐VP), methyl methacrylate (MMA) or cinnamic acid (CA) as the functional monomer, respectively. The prepared nano‐MIPs were characterized by transmission electron microscope (TEM) and Raman, whereas MIMs were characterized by SEM, membrane flux, and selective adsorption experiments. Morphological analysis exhibited that the addition of nano‐MIPs improved the formation of ordered and well‐defined porous membrane morphology. Compared with MMA‐MIM and CA‐MIM, the 4‐VP‐MIM exhibited higher membrane flux, adsorption capacity, and stronger selective binding for phenol as well as excellent permeation selectivity for phenol. Moreover, the selective effect of 4‐VP‐MIM on phenol was strongly affected by the amount of 4‐VP imprinted nanoparticles (nano‐4‐VP‐MIPs). The experimental data revealed that the 4‐VP‐MIM containing 2.0 wt % of nano‐4‐VP‐MIPs exhibited the highest separation selectivity for the template phenol, whose selectivity coefficients for phenol relative to salicylic acid (SA) and p‐hydroxybenzoic acid (p‐HB) were 5.6770 and 5.5433, respectively, which was close to the predicted selectivity coefficient value. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42350.