Chiral separation of 1,1′‐bi‐2‐naphthol and its analogue on molecular imprinting monolithic columns by HPLC

Ou, Junjie; Tang, Shouwan; Zou, Hanfa

doi:10.1002/jssc.200500165

Cited by 21 publications

(12 citation statements)

References 26 publications

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“…Molecularly imprinted polymers (MIPs) are tailor‐made materials with high selectivity for a template and have been intensively studied in the recent years. 1, 2 MIPs have been exploited for several applications such as chemical sensors, 3, 4 capillary electrochromatography, 5, 6 enantiomer separations, 7, 8 artificial antibodies, 9–11 HPLC stationary phases, 1, 12, 13 and solid‐phase extraction. 14–16 In general, MIPs are prepared by bulk polymerization method.…”

Section: Introductionmentioning

confidence: 99%

Clozapine recognition via molecularly imprinted polymers; bulk polymerization versus precipitation method

Mohajeri

Karimi

Aghamohammadian

et al. 2011

J of Applied Polymer Sci

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Two clozapine (CLZ) imprinted polymers were prepared by bulk and precipitation methods. Methacrylic acid and ethylene glycol dimethacrylate (EDMA) were used as functional and crosslinker monomers, respectively. The mean diameter and particle size distribution of the imprinted (P-MIP) and nonimprinted (P-NIP) particles obtained in precipitation method were examined. A conventional batch-adsorption test was applied for characterization of CLZ-polymer interaction. Dissociation constant (K D ) and maximum binding sites (B max ) were calculated using Scatchard analysis. To evaluate the recognition properties of polymers, phenytoin (PTN) binding to each polymer was also studied and compared to CLZ. The imprinting factor (IF) and selectivity factor (a) were also determined for each polymer. Average diameter and polydispersity of P-MIP were 925 nm and 0.17, respectively. The data for P-NIP were 1.05 lm and 0.18. The K D , IF, and a values calculated for P-MIP were 0.45 lM, 3.26, and 17.43, respectively. The data for imprinted polymer, prepared by bulk polymerization (B-MIP), were 14.5 lM, 1.95, and 3.67. These results demonstrated that precipitation polymerization is a more convenient, more effective, and more reproducible method than bulk polymerization for the synthesis of uniformly sized micron and submicronimprinted polymer particles.

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Section: Introductionmentioning

confidence: 99%

Clozapine recognition via molecularly imprinted polymers; bulk polymerization versus precipitation method

Mohajeri

Karimi

Aghamohammadian

et al. 2011

J of Applied Polymer Sci

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“…Ou et al. reported the preparation of molecularly imprinted monolithic polymer columns with ( R )‐(+)‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol and ( S )‐(−)‐1,1′‐bi‐2‐naphthol as the template molecules, respectively. The authors used in situ polymerization using ethylene dimethacrylate and 4‐vinylpyridine as cross‐linker and functional monomer, respectively.…”

Section: Preparation Of Monolithic Chiral Stationary Phasesmentioning

confidence: 99%

“…Ou et al. reported the chiral separation of ( R , S )‐1,19‐bi‐2‐naphthol on MIP monolithic columns having ( R )‐(+)‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol and ( S )‐(−)‐1,1′‐bi‐2‐naphthol as template molecules, respectively. The authors claimed that hydrogen bonding interactions in acetonitrile and hydrophobic interactions in aqueous solution among enantiomers and polymers were responsible for the retention and resolution.…”

Section: Applicationsmentioning

confidence: 99%

“…The authors described separation mechanism and reported hydrophobic interactions, and ionic and/or hydrogen bonding forces responsible for the recognition mechanism. Ou et al [87] reported the chiral separation of (R,S)-1,19-bi-2-naphthol on MIP monolithic columns having (R)-(+)-5,5 ,6,6 ,7,7 ,8,8octahydro-1,1 -bi-2-naphthol and (S)-(−)-1,1 -bi-2-naphthol as template molecules, respectively. The authors claimed that hydrogen bonding interactions in acetonitrile and hydrophobic interactions in aqueous solution among enantiomers and polymers were responsible for the retention and resolution.…”

Section: Capillary Electrochromatographymentioning

confidence: 99%

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Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography

2014

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During the last decade, chiral monolithic stationary phases have been prepared and used for rapid enantioseparations in CEC and HPLC. Various chiral selectors are used to prepare these CSPs. The preparation, properties, and applications of these CSPs are discussed in this paper. Attempts have been made to describe optimization strategies and the chiral recognition mechanisms. A comparison of chiral separations in CEC and HPLC is described. Efforts have also been made to predict the future perspectives and challenges of chiral monolithic stationary phases. The most effective chiral selectors include polysaccharides, cyclodextrins, and macrocyclic glycopeptide antibiotics. These chiral phases produced acceptable analytical enantiomeric separation of a variety of racemates. However, the development of these CSPs for preparative-scale separations is needed.

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“…Molecularly imprinted materials offer attractive properties such as stability, ease of preparation, environment friendly, and low cost for demanding or special analytical tasks [11][12][13]. Hence, CEC-based MIP monoliths have the potential to be a powerful tool in the chiral separation field, possessing not only predictable recognition ability but also the elution order [14][15][16][17][18]. Traditionally, MIPs are fabricated using one func- tional monomer, namely methacrylic acid (MAA).…”

Section: Introductionmentioning

confidence: 99%

A molecularly imprinted monolith for the fast chiral separation of antiparasitic drugs by pressurized CEC

Liao

Wang

Lin

et al. 2010

J of Separation Science

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Molecularly imprinted polymer (MIP) monoliths with (S)-ornidazole ((S)-ONZ) as the template molecule have been designed and prepared by the simple thermal polymerization of methacrylic acid, 4-vinylpyridine, and ethylene dimethacrylate in the presence of a binary porogenic mixture of toluene and dodecanol. The influences of polymerization mixture composition on the chiral recognition of ONZ have been evaluated, and the imprint effect in the optimized MIP monolith has been clearly demonstrated. The new monolithic stationary phase with optimized porous property and good selectivity was used for the chiral separation of ONZ by pressurized CEC. The pressurized CEC conditions were also optimized to obtain the good chiral separation. The enantiomers were rapidly separated within 9 min on the MIP-based chiral stationary phase, whereas the chiral separation was not obtained on the nonimprinted polymer. Additionally, the proposed method has been successfully applied to the chiral separation of ONZ in tablet samples by injection of the crude sample. The cross-selectivity for similar antiparasitic drug was investigated. The results indicated that the chiral separation of secnidazole could also be obtained on the optimized MIP monolith within 14 min.

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Chiral separation of 1,1′‐bi‐2‐naphthol and its analogue on molecular imprinting monolithic columns by HPLC

Cited by 21 publications

References 26 publications

Clozapine recognition via molecularly imprinted polymers; bulk polymerization versus precipitation method

Clozapine recognition via molecularly imprinted polymers; bulk polymerization versus precipitation method

Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography

A molecularly imprinted monolith for the fast chiral separation of antiparasitic drugs by pressurized CEC

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