Influence of polymer morphology on the ability of imprinted network polymers to resolve enantiomers

Sellergren, Börje; Shea, Kenneth J.

doi:10.1016/0021-9673(93)83112-6

Cited by 403 publications

(323 citation statements)

References 29 publications

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“…As reported by Sellergren and Shea, 23 the pore diameter seems to be relatively large (about 1500 Å) even under dry conditions. However, the contribution of intraparticle convective flow to mass transfer is probably negligible because of the low flow velocity of the mobile phase.…”

Section: Chromatographic Conditionssupporting

confidence: 70%

Kinetic Study of the Concentration Dependence of the Mass Transfer Rate Coefficient in Enantiomeric Separation on a Polymeric Imprinted Stationary Phase

Miyabe

Guiochon

2000

ANAL. SCI.

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Molecular imprinting is a most attractive method of preparation of dedicated stationary phases for chromatography. Its use for enantioseparations is attracting considerable interest. 1,2 Imprinted materials can provide a very high selectivity for the objective compound, i.e., the imprinted molecule. [1][2][3][4][5] Although analytical applications are rapidly developing, the situation on the preparative front is less rosy. 1 Columns packed with imprinted stationary phases exhibit a poor efficiency and elution peaks are often unsymmetrical, especially for the more retained enantiomer. Sellergren et al. 1,2 suggested that the nonlinear behavior of the adsorption isotherm was the main cause of the broad and unsymmetrical bands observed for L-phenylalanine anilide (PA) on an L-PA imprinted chiral stationary phase. Although the possibility of a slow mass transfer kinetics was also pointed out, no detailed study supported this assumption. Yet, information on the mass transfer characteristics of imprinted stationary phases is necessary to clarify strategies for the improvement of these materials.Most kinetic studies in chromatography assume that four mass transfer processes are involved in a column, (1) axial dispersion, (2) fluid-to-particle mass transfer, (3) intraparticle diffusion, and (4) adsorption/desorption. 6 The contributions of these four processes to peak spreading are evaluated separately. Axial dispersion and the fluid-to-particle mass transfer resistance are inherent to flow processes through packed beds. They are well understood, relatively easy to control, and their contributions are often small. By contrast, intraparticle diffusion and adsorption/desorption give often larger contributions to the mass transfer resistance in the column. Their properties are intrinsic to each packing material and they are still often poorly understood. In order to evaluate the actual performance of packing materials, the characteristics of the mass transfer kinetics inside stationary phase particles must be clarified.Sajonz et al. 7 measured the adsorption equilibrium isotherm and the mass transfer kinetics of L-and D-PA on a polymeric stationary phase imprinted with L-PA, using a staircase frontal analysis method. The isotherm was well represented by either the Bi-Langmuir or the Freundlich models, but not by the simple Langmuir isotherm. The equilibrium data suggested that the distribution of the adsorption energy on the surface of the imprinted stationary phase is heterogeneous and showed that this phase has a high selectivity for the imprinted L-enantiomer. The lumped mass transfer rate coefficient (km,L) was calculated from each single breakthrough curve by applying the transport model of chromatography. 6 The values of km,L increased with increasing concentration of the enantiomers. The extent of the positive concentration dependence of km,L was larger for L-PA than for D-PA. It is expected that a more detailed analysis of the overall mass transfer rate parameter, km,L, could provide new, useful information and all...

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Section: Chromatographic Conditionssupporting

confidence: 70%

Kinetic Study of the Concentration Dependence of the Mass Transfer Rate Coefficient in Enantiomeric Separation on a Polymeric Imprinted Stationary Phase

Miyabe

Guiochon

2000

ANAL. SCI.

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“…It has been reported that a porogenic solvent can affect the structure and morphology of a MIP, and the retention of an analyte on the MIP. 15 As expected, there are large differences in the retention, selectivity and enantioseparation factors of nilvadipine among MIPs 4 -7. Figure 5 shows the effect of a toluene concentration used as a mobile phase on the retention, selectivity and enantioseparation factors of nilvadipine on MIPs 4 -7, which are prepared using toluene, chloroform, cyclohexanol and phenylacetonitrile, respectively, as the porogens.…”

Section: Effect Of Porogensupporting

confidence: 58%

Retentivity and Enantioselectivity of Uniformly-sized Molecularly Imprinted Polymers for (S)-Nilvadipine in Aqueous and Non-Aqueous Mobile Phases

2005

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Uniformly-sized molecularly imprinted polymers (MIPs) for (S)-nilvadipine have been prepared by a multi-step swelling and polymerization method using methacrylic acid or 4-vinylpyridine (4-VPY) as a functional monomer, ethylene glycol dimethacrylate (EDMA) as a cross-linker, and toluene, chloroform, cyclohexanol or phenylacetonitrile as a porogen. The chiral recognition abilities of the MIPs for nilvadipine were evaluated using aqueous and non-aqueous mobile phases. Among the MIPs, the (S)-nilvadipine-imprinted 4-VPY-co-EDMA polymers prepared using toluene as a porogen showed the highest recognition ability for nilvadipine in both aqueous and non-aqueous mobile phases. In addition to molecular shape recognition, hydrogen-bonding interactions of the NH proton of nilvadipine with a pyridyl group of the (S)-nilvadipine-imprinted 4-VPY-co-EDMA polymers could play an important role in the retention and chiral recognition of nilvadipine in aqueous and non-aqueous mobile phases. Furthermore, the MIP for (S)-nilvadipine gave the highest molecular recognition ability when a porogenic solvent during polymerization was used as the mobile phase modifier.

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“…ionic, hydrophobic and hydrogen bonding. The non-covalent imprinting approach seems to hold more potential for the future of molecular imprinting due to the vast number of compounds, including biological compounds, which are capable of non-covalent interactions with functional monomers [29][30]. Limits to the non-covalent molecular imprinting are set by the peculiar molecular recognition conditions.…”

Section: Non-covalent Approachmentioning

confidence: 99%

Characteristic and Synthetic Approach of Molecularly Imprinted Polymer

Yan

Row

2006

IJMS

462

231

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Abstract:Molecularly imprinted polymers (MIP) exhibiting high selectivity and affinity to the predetermined molecule (template) are now seeing a fast growing research. However, optimization of the imprinted products is difficult due to the fact that there are many variables to consider, some or all of which can potentially impact upon the chemical, morphological and molecular recognition properties of the imprinted materials. This review present a summary of the principal synthetic considerations pertaining to good practice in the polymerization aspects of molecular imprinting, and is primarily aimed at researcher familiar with molecular imprinting methods but with little or no prior experience in polymer synthesis. The synthesis, characteristic, effect of molecular recognition and different preparation methods of MIP in recent few years are discussed in this review, unsolved problems and possible developments of MIP were also been briefly discussed.

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Influence of polymer morphology on the ability of imprinted network polymers to resolve enantiomers

Cited by 403 publications

References 29 publications

Kinetic Study of the Concentration Dependence of the Mass Transfer Rate Coefficient in Enantiomeric Separation on a Polymeric Imprinted Stationary Phase

Kinetic Study of the Concentration Dependence of the Mass Transfer Rate Coefficient in Enantiomeric Separation on a Polymeric Imprinted Stationary Phase

Retentivity and Enantioselectivity of Uniformly-sized Molecularly Imprinted Polymers for (S)-Nilvadipine in Aqueous and Non-Aqueous Mobile Phases

Characteristic and Synthetic Approach of Molecularly Imprinted Polymer

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