Chiral separation with polyurea membrane consisting of L‐lysinyl residue: Proposal of facile method for prediction of permselectivity

Novel chiral polyureas were prepared from L ‐lysine‐4‐nitroanilide and 2,4‐toluene diisocyanate. The polyurea thus prepared gave a durable self‐standing membrane that can be directly converted into molecular recognition membranes by applying an alternative molecular imprinting. The Z‐D ‐glutamic acid (D ‐Glu) molecularly imprinted membrane adsorbed D ‐Glu in preference to L ‐glutamic acid (L ‐Glu) from racemic mixture of Glu and vice versa. Those two types of molecularly imprinted membrane showed optical resolution ability, adopting a concentration gradient as a driving force for membrane transport. A facile method to predict permselectivity of racemic mixture of charged permeant was proposed. From the observed membrane resistance, the permselectivity was predicted. The predicted permselectivity coincided with the observed one. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Optical Resolution Membranes from Polysulfones Bearing Alanine Derivatives as Chiral Selectors

Polysulfones bearing a derivative of alanyl residue employed as chiral selectors were prepared by polymer modification. The specific rotation ([α]_D) of the polysulfone with a derivative of D ‐alanyl residue (PSf‐Ac‐D ‐Ala) was determined to be 2.87 deg · cm² · g^?1 (c = 1.00 g · dL^?1 in DMF) and that with L ‐alanyl residue (PSf‐Ac‐L ‐Ala) to be ‐2.36 deg · cm² · g^?1 (c = 1.00 g · dL^?1 in DMF). The membrane from PSf‐Ac‐D ‐Ala preferentially adsorbed the D ‐isomer of Glu from racemic mixture of Glu and vice versa. Chiral separation ability was studied by applying a potential difference as a driving force for membrane transport. The permselectivity of PSf‐Ac‐D ‐Ala toward D ‐Glu (α_D/L) was determined to be 1.40, and that of PSf‐Ac‐L ‐Ala toward the L ‐isomer (α_L/D) to be 1.48 at 18.0 V, reflecting their adsorption selectivity.

     

Preparation and characterization of metal-complex imprinted PVDF hollow fiber membranes

Using nickel-2,2′-dipyridyl complex as a template, N-vinyl-2-pyrrolidone as the metal coordination functional monomer, and ethylene glycol dimethacrylate as the crosslinker, polyvinylidene fluoride (PVDF) hollow fiber ultrafiltration membrane as the supported membrane, metal complex imprinted polymeric membranes were prepared. The association constant of template-monomer interaction in the prepolymerization solution was estimated to be 4.38 × 10⁴ (L/mol)² by spectrophotometric titration analysis. The attenuated total reflection Fourier transform infrared spectroscopy and scanning electron micrograph characterization indicated that the surface of the support PVDF membrane was completely coated by the imprinted polymer layer after modification. The imprinted membranes exhibited the selective permeability for the template in certain nickel acetate solution. The molecularly imprinted membranes gave higher permeation separation factors at about pH 6, whereas increasing pressure would lower the separation ability. The effects of ion concentration, cations and counterions, ligand selectivity, pH, and trans-membrane pressure were investigated and the permeation performances of the imprinted membranes could be regarded as facilitated transport mechanism. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

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.     

Molecular‐imprinted nylon membranes for the permselective binding of phenylalanine as optical‐resolution membrane adsorbents

Nylon 6, nylon 6,6, and terephthalic phenylene polyamide (TPPP) were functionalized by phase‐inversion molecular imprinting to add L ‐phenylalanine recognition ability. Formic acid containing 20 wt % nylon and 8 wt % L ‐phenylalanine was used as the solvent for the cast solution of the imprinting process. The resultant porous membranes behaved as membrane adsorbents that separated the L /D mixture of the substrate. The imprinted nylon 6 and nylon 6,6 presented high selectivity to the L ‐form substrate with respect to the TPPP membranes, but the imprinted TPPP membranes showed higher binding capacity with 0.57 μmol/g for L ‐phenylalanine. The apparent partition coefficients of L ‐ and D ‐forms by the imprinted membranes were 6.8, 4.2, and 1.7 for nylon 6, nylon 6,6, and TPPP, respectively. The separation manner of the L ‐ and D ‐forms from the mixture was also confirmed by membrane filtration under 1.5 kgf/cm² of applied pressure. The imprinted nylon 6, nylon 6,6, and TPPP membranes had separation factors of L ‐ and D ‐phenylalanines of 1.1, 1.1, and 1.2, respectively. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 620–626, 2005     

Optical resolution of racemic amino acid derivatives with chiral polyamides bearing glutamyl residue as a diacid component

Novel chiral polyamides with chiral environment in their main chains were obtained from aromatic diamine, 4,4′‐diaminodiphenylmethane (DADPM), and the D ‐isomer or the L ‐isomer of N‐α‐protected glutamic acid, such as N‐α‐benzyloxycarbonyl‐D ‐glutamic acid (Z‐D ‐Glu‐OH) or N‐α‐benzyloxycarbonyl‐L ‐glutamic acid (Z‐L ‐Glu‐OH), in the presence of triphenyl phosphite (TPP). Two types of newly prepared polyamide showed optical rotation, implying that there were asymmetric carbons in their main chains. Circular dichroism studies demonstrated that resulting chiral poly‐ amides took a helical structure. Optical resolution ability of those two types of polyamide was studied by adopting potential difference as a driving force for membrane transport. Membranes showed permselectivity toward racemic mixture of N‐α‐acetyltryptophan (Ac‐Trp). The permselectivity was dependent on the absolute configuration of diacid component. The permselectivity was expressed by diffusivity selectivity, which was determined by the presence of chiral helicity. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Transport selectivity of tribenuron‐methyl imprinted polymer nanowire membrane prepared using N,O‐bismethacryloyl ethanolamine as a functional crosslinking monomer

Using tribenuron‐methyl as a template and N,O‐bismethacryloyl ethanolamine as a functional crosslinking monomer, a molecularly imprinted nanowire membrane was prepared over an anodic alumina oxide membrane. The nanowire fabric of the imprinted membrane was established with a scanning electron microscope and a transmission electron microscope. However, the nonimprinted particulate membrane is formed in the absence of a template. Scatchard analysis showed that an equal class of binding sites were formed in the imprinted nanowire membrane and the dissociation constant and the maximum number of these binding sites were estimated to be 1.44 × 10⁻⁵ M and 22.7 µmol/g, respectively. The permeation experiments throughout the imprinted membrane and the nonimprinted one were carried out in a solution containing the template and its competitive analogs. These results demonstrated that the molecularly imprinted nanowire membrane exhibited higher transport selectivity for the template tribenuron‐methyl than its analogs, chlorimuron‐ethyl, thifensulfuron‐methyl and N‐(4‐bromophenylcarbamoyl)‐5‐chloro‐1H‐benzo[d]imidazole‐2‐carboxamide. But the nonimprinted granular membrane had no permselectivity for the four substrates. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Molecularly imprinted fluorescent polymers as chemosensors for the detection of mercury ions in aqueous media

This article describes the investigation of molecularly imprinted fluorescent polymer membranes as sensing receptors for Hg²⁺ detection by an optical approach. The polymers were synthesized with 4‐vinylpyridine as a functional monomer and Hg²⁺ as a template; 9‐vinylcarbazole was used as both a complex‐forming agent and a fluorescence probe. The free‐radical polymerization was performed within a semicylindrical Teflon mold and was initiated by 2,2′‐azobisisobutyronitrile at 60°C. The template, ion‐bonded to pyridine and carbazole groups in the polymer membrane, was removed by acid treatment. Attenuated total reflectance–Fourier transform infrared (FTIR) spectroscopic measurements and scanning electron microscopy images were used to compare the chemistry and surface morphology, respectively, of both imprinted and nonimprinted polymer materials. The final polymer membranes with semicylindrical shapes were used directly to determine Hg²⁺ concentration in aqueous solutions by the monitoring of the fluorescence intensity of the carbazole groups quenched upon complex formation with metal ions. The values of the Hg²⁺ binding ratio for the imprinted and nonimprinted polymeric membranes were compared, and the results indicate the superior sensitivity and selectivity of the imprinted membranes. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Molecularly imprinted polymers for the selective recognition of l‐phenylalanine based on 1‐buty‐3‐methylimidazolium ionic liquid

To enhance the affinity of 4‐vinyl pyridine to l ‐phenylalanine (l ‐Phe) and convert the imprinting process from the aqueous phase to the organic phase, an oil‐soluble amino acid ionic liquid was introduced as a template. In this study, 1‐butyl‐3‐methylimidazolium α‐aminohydrocinnamic acid salt was first applied to prepared surface molecularly imprinted polymers (MIPs) in acetonitrile for the selective recognition of l ‐Phe. Fluorescence quenching analysis of the functional monomer on the template was investigated under different conditions to study the imprinting mechanism. Several binding studies, such as the sorption kinetics, sorption thermodynamics, and solid‐phase extraction application, and the chiral resolution of racemic phenylalanine were investigated. The binding isotherms were fitted by nonlinear regression to the Freundlich model to investigate the recognition mechanism. The affinity distribution analysis revealed that polymers imprinted by ionic liquid showed higher homogeneous binding sites than those imprinted by l ‐Phe. The competition tests were conducted by a molecularly imprinting solid‐phase extraction procedure to estimate the selective separation properties of the MIPs for l ‐Phe. The target MIP was shown to be successfully for the separation of l ‐Phe from an amino acid mixture. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42485.     

DNA adsorption on a poly‐L‐lysine‐immobilized poly(2‐hydroxyethyl methacrylate) membrane

The DNA adsorption properties of poly‐L ‐lysine‐immobilized poly(2‐hydroxyethyl methacrylate) (pHEMA) membrane were investigated. The pHEMA membrane was prepared by UV‐initiated photopolymerization and activated with epichlorohydrin. Poly‐L ‐lysine was then immobilized on the activated pHEMA membrane by covalent bonding, via a direct chemical reaction between the amino group of poly‐L ‐lysine and the epoxy group of pHEMA. The poly‐L ‐lysine content of the membrane was determined as 1537 mg m^?2. The poly‐L ‐lysine‐immobilized membrane was utilized as an adsorbent in DNA adsorption experiments. The maximum adsorption of DNA on the poly‐L ‐lysine‐immobilized pHEMA membrane was observed at 4 °C from phosphate‐buffered salt solution (pH 7.4, 0.1 M; NaCl 0.5 M) containing different amounts of DNA. The non‐specific adsorption of DNA on the plain pHEMA membrane was low (about 263 mg m^?2). Higher DNA adsorption values (up to 5849 mg m^?2) were obtained in which the poly‐L ‐lysine‐immobilized pHEMA membrane was used. Copyright © 2003 Society of Chemical Industry     

Side chain functionality dominated the chromatography of N‐protected amino acid on molecularly imprinted polymer

Molecularly imprinted polymer (MIP) with N^α‐protected amino acid as the print molecule was prepared and used as the stationary phase for the chromatographic study of molecular recognition. Particles of MIP were prepared by photopolymerization of 4‐vinylpyridine in the presence of tert‐butyloxycarbonyl‐L ‐tyrosine (Boc‐L ‐Tyr) and packed into a column for the chromatographic resolution of Boc‐L ‐Tyr and tert‐butyloxycarbonyl‐L ‐phenylalanine (Boc‐L ‐Phe). These two N^α‐protected amino acids that differ from each other in the side chain with one hydroxyl group on the benzene ring could be well separated on the MIP. A separation factor of about two was achieved by using a mixture of acetonitrile (99.5 v/v %) and acetic acid (0.5 v/v %) as the mobile phase. Results suggest that the interaction between hydroxyl group in the side chain of amino acid and pyridine in the polymer dominated the selective adsorption of print molecule on the MIP. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2007     

Recognition and Selective Transport of Nucleic Acid Components through Molecularly Imprinted Polymeric Membranes

To induce “molecular memory” in a membrane substrate at the same time that the membrane was prepared from its polymer solution, an alternative molecular imprinting technique was applied. Upon membrane formation, a “molecular memory” of the imprint molecule is retained by the formed membrane that recognizes or favors interaction with print molecule analogues. In the present study, polystyrene resin bearing a tetrapeptide derivative, a derivative of natural polymer, and an entirely non‐chiral synthetic polymer were adopted as candidate materials to form molecular recognition sites. 9‐Ethyladenine was adopted as a print molecule. These molecularly imprinted polymeric membranes recognized and adsorbed adenosine ( As ), which is an analogue of the print molecule, in preference to guanosine ( Gs ) from As / Gs mixtures. However Gs was permeated in preference to As contrary to adsorption selectivity, possibly because of the relatively high affinity between As and the membrane.     

Nickel(II)‐imprinted monolithic columns for selective nickel recognition

Ni²⁺‐imprinted monolithic column was prepared for the removal of nickel ions from aqueous solutions. N‐Methacryloyl‐L ‐histidine was used as a complexing monomer for Ni²⁺ ions in the preparation of the Ni²⁺‐imprinted monolithic column. The Ni²⁺‐imprinted poly(hydroxyethyl methacrylate‐N‐methacryloyl‐L ‐histidine) (PHEMAH) monolithic column was synthesized by bulk polymerization. The template ion (Ni²⁺) was removed with a 4‐(2‐pyridylazo) resorcinol (PAR):NH₃? NH₄Cl solution. The water‐uptake ratio of the PHEMAH–Ni²⁺ monolith increased compared with PHEMAH because of the formation of nickel‐ion cavities in the polymer structure. The adsorption of Ni²⁺ ions on both the PHEMAH–Ni²⁺ and PHEMAH monoliths were studied. The maximum adsorption capacity was 0.211 mg/g for the PHEMAH–Ni²⁺ monolith. Fe³⁺, Cu²⁺, and Zn²⁺ ions were used as competitive species in the selectivity experiments. The PHEMAH–Ni²⁺ monolithic column was 268.8, 25.5, and 10.4 times more selective than the PHEMAH monolithic column for the Zn²⁺, Cu²⁺, and Fe³⁺ ions, respectively. The PHEMAH–Ni²⁺ monolithic column could be used repeatedly without a decrease in the Ni²⁺ adsorption capacity. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Molecularly imprinted polymers by phase inversion technique for the selective recognition of saccharides of biomedical interest in aqueous solutions

The purpose of this work was the preparation and characterization of polymeric membranes for the selective recognition of saccharides using molecular imprinting technology associated with phase inversion. A system able to bind saccharides with high selectivity is particularly important in the pharmaceutical sector, since some of these compounds are constituents of molecules which can exert serious toxic effects even at very low concentrations. Two polymeric matrices were prepared using poly(ethylene‐co‐vinyl alcohol) copolymers, with an ethylene molar content of 32% and 44%, and were imprinted with two different saccharide molecules: maltose and 2‐keto‐3‐deoxy‐d ‐manno‐octulosonate (KDO). Matrices imprinted against maltose and KDO showed an easy template extraction, high binding capability and satisfactory selectivity, particularly for the matrix with an ethylene molar content of 44%. © 2017 Society of Chemical Industry     

Synthesis of ion‐imprinting chitosan/PVA crosslinked membrane for selective removal of Ag(I)

A novel ion‐imprinted membranes were synthesized for selective removal and preconentration for Ag(I) ions from aqueous solutions. The membranes were obtained via crosslinking of chitosan (CS), PVA, and blend chitosan/PVA using glutaraldehyde (GA) as crosslinker. The FTIR spectra were used to confirm the membrane formation. Comparing with the nonimprinted membranes, Ag(I)‐imprinted CS and CS/PVA has higher removal capacity and selectivity for Ag⁺ ions. An enhancement in the Ag⁺ removal capacity by ～ 20% (from 77.8 to 94.4 mg g^–1) and ～ 50% (from 83.9 to 125 mg g^–1) was found in the Ag(I)‐imprinted CS and Ag(I)‐imprinted CS/PVA membranes, respectively, when compared with the nonimprinted membranes. Removal equilibra was achieved in about 40 min for the non‐ and ion‐imprinted CS/PVA. The pH and temperature significantly affected the removal capacity of ion‐imprinted membrane. The relative selectivity coefficient values of Ag⁺/Cu²⁺ and Ag⁺/Ni²⁺ are 9 and 10.7 for ion‐imprinted CS membrane and 11.1 and 15 for ion‐imprinted CS/PVA membrane when compared with nonimprinted membranes. The imprinted membranes can be easily regenerated by 0.01M EDTA and therefore can be reused at least five times with only 15% loss of removal capacity. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Molecularly imprinted electrochemical sensor for the determination of ampicillin based on a gold nanoparticle and multiwalled carbon nanotube‐coated pt electrode

A novel molecularly imprinted electrochemical sensor was developed for the sensitive and selective determination of ampicillin (AMP). The sensor was prepared on a platinum electrode modified with multiwalled carbon nanotubes (MWCNTs), gold nanoparticles (AuNPs), and a thin film of molecularly imprinted polymers (MIPs). MWCNTs and AuNPs were introduced to enhance the sensor's electronic transmission and sensitivity. The molecularly imprinted polymer (MIP) was synthesized using AMP as the template molecule, methacrylic acid as functional monomer, and ethylene glycol maleic rosinate acrylate (EGMRA) as cross‐linker. The performance of the proposed imprinted sensor was investigated using cyclic voltammetry (CV), differential pulse voltammetry (DPV), and electrochemical impedance spectroscopy (EIS). The results showed that the imprinted film displayed a fast and sensitive response to AMP. Under optimal conditions, response peak current had a linear relationship with the concentration of AMP in the range of 1.0 × 10^?8 mol/L to 5.0 × 10^?6 mol/L and a detection limit of 1.0 × 10^?9 mol/L (S/N = 3). This imprinted sensor was used to detect AMP in food samples with recoveries of 91.4–105%. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 40613.     

Preparation of Fe3O4/poly(l‐glutamic acid) microspheres and their adsorption of Cu(II) ions

Fe₃O₄/poly(l ‐glutamic acid) (P‐l ‐Glu) magnetic microspheres were synthesized in an l ‐glutamic acid solution by coprecipitation and a dehydration condensation reaction and were characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, and ζ‐potential measurement. P‐l ‐Glu was coated on the surface of Fe₃O₄ microspheres. The average particle diameter of Fe₃O₄/P‐l ‐Glu was 388 nm and dispersed homogeneously in water. The adsorption of Cu(II) ions on Fe₃O₄/P‐l ‐Glu was further studied. The effect of different pH values and reaction times on the adsorption of Fe₃O₄/P‐l ‐Glu was discussed. The adsorption equilibrium was reached in 40 min, and the maximum adsorption for Cu(II) ions was more than 500 mg/g; this value occurred at pH 8 in water. The adsorption dynamic process fit the Freundlich isotherms well, and the adsorption kinetics followed the adsorption mechanism of the pseudo‐second‐order equation, which was the main complexation reaction. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 43730.     

Synthesis and characterization of amphiphilic biodegradable poly(glutamic acid‐co‐lactic acid‐co‐glycolic acid) by direct polycondensation

Poly(glutamic acid‐co‐lactic acid‐co‐glycolic acid) (PGLG), an amphiphilic biodegradable copolymer, was synthesized by simply heating a mixture of L ‐glutamic acid (Glu), DL ‐lactic acid, and glycolic acid with the present of stannous chloride. The unique branched architecture comprising of glutarimide unit, polyester unit, and polyamide unit was confirmed by NMR spectrum. The PGLG was soluble in many organic solvents and aqueous solution of sodium hydroxide (pH ≥ 9.0). The thermal properties were evaluated using thermogravimetric analysis and differential scanning calorimetry. Molecular weights were determined by ¹H NMR end‐group analysis and GPC, respectively, and the results indicated that the higher Glu content resulted in a decrease of the molecular weight. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Using polystyrene‐co‐maleic acid for molecularly imprinted membranes prepared in supercritical carbon dioxide

Supercritical CO₂ (ScCO₂) has been used to prepare molecularly imprinted polymers of poly(styrene‐co‐maleic acid) (PSMA) for targeted uracil (URA). The condition of ScCO₂ was on 16 MPa between 35 and 50°C. The resultant imprinted membranes prepared at 35 and 50°C bound URA with 9.2 ± 0.10 and 12.6 ± 0.06 μmol g⁻¹, respectively. Competitive binding studies were undertaken in binary substrate solution containing each of URA/DMURA, URA/Thymine, and URA/Cytosine with 2 μM. The URA imprinted membrane showed high separation factor (α) with 17 for both URA/DMURA and URA/Thymine and for URA/Cytosine, α = 13. Results strongly suggested that the URA imprinted membrane had effective selectivity hydrogen bonding to separately bind in the binary components to the template. Effect of organic solvents on the URA imprinting in ScCO₂ was also studied, in addition to comparison of properties with those obtained in both ScCO₂ and water. Evidence presented that ScCO₂ medium was effective to prepare the URA imprinted membrane. We discussed that ScCO₂ fluid was efficient to fix the shape of URA template into the PSMA membrane through hydrogen bonding. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Synthesis of novel photoresponsive molecularly imprinted polymer microspheres with special binding properties

An azobenzene‐containing molecularly imprinting polymer microsphere with photoresponsive binding properties toward 2,4‐dichlorophenoxyacetic acid (2,4‐D) was successful prepared via silica surface polymerization. The number‐average diameters of silica and imprinting polymer microsphere are 0.5 and 0.7 μm, respectively. The static adsorption, binding and selectivity experiments were performed to investigate the adsorption properties and recognition characteristics of the polymers for 2,4‐D. The equilibrium adsorptive experiments indicated that 2,4‐D‐SMIP(surface molecularly imprinted polymers) has significantly higher adsorption capacity for 2,4‐D than its nonimprinted polymers (SNIP).The binding constant K_d and apparent maximum number Q_max of the imprinted polymer were determined by Scatchard analysis as 0.054 mmol L^?1 and 0.167 mmol g^?1_, respectively. The result of photoregulated release and uptake of 2,4‐D experiment demonstrated that azo‐containing SMIP can make use of light and change it into mechanical properties to release and take up the template molecules. It means that the SMIP can be controlled by light. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 130: 869‐876, 2013