Chromatographic evaluation of poly (trans-1,2-cyclohexanediyl-bis acrylamide) as a chiral stationary phase for HPLC

Zhong, Qiqing; Han, Xinxin; He, Lixia; Beesley, Thomas E.; Trahanovsky, Walter S.; Armstrong, Daniel W.

doi:10.1016/j.chroma.2004.12.088

Cited by 41 publications

(36 citation statements)

References 27 publications

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“…In this way, the polymerization was confined to the surface of solid support or in the vicinity of surface and the undesirable solution polymerization was limited by the diffusion of radical to the bulk solution [25]. Therefore, compared with the ''grafting to'' method, high polymer grafting density can be achieved by this ''grafting from'' method [23,25,27].…”

Section: Introductionmentioning

confidence: 96%

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Grafting of silica with a hydrophilic triol acrylamide polymer via surface‐initiated “grafting from” method for hydrophilic‐interaction chromatography

Peng

Yuan

2011

J of Separation Science

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A novel hydrophilic polymer-coated silica sorbent has been prepared using the radical "grafting from" polymerization method through surface-bound azo initiators for hydrophilic-interaction chromatography (HILIC). The azo groups were introduced to the surface of silica gel through the reaction with amino groups on the surface of silica gel with 4,4'-azobis(4-cyanopentanoic acid chloride) (ACVC). The resultant azo-immobilized silica gel served as surface initiator to polymerize hydrophilic triol acrylamide monomer N-acryloyltris(hydroxymethyl) aminomethane (NA) in methanol to get hydrophilic polymer-coated silica sorbent. The obtained poly(NA)-coated silica (pNA-sil) was characterized by Fourier transform infrared spectroscopy (FT-IR), elemental analysis (EA), and nitrogen sorption porosimetry (NSP). Then the pNA-sil was packed into the stainless-steel column and evaluated in high-performance liquid chromatography (HPLC). Good chromatographic performance for the separation of peptides and nucleosides was obtained under HILIC mode. The results indicated that the pNA-sil stationary phase behaved as mixed-mode retention mechanisms of hydrophilic and ionic interactions. Furthermore, the pNA-sil phase was used to separate tryptic digest of β-casein and our results showed that more than 12 peptides peaks were resolved and well distributed within the elution window. Finally, the pNA-sil stationary phase was demonstrated to possess remarkable reproducibility and stability. Taken together, the pNA-sil stationary phase prepared in the current study offers a potential application in proteomics study.

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Section: Introductionmentioning

confidence: 96%

“…In recent years, polymer-coating inorganic materials have brought great interests for serving as chromatographic packing materials [13,16,18,21,23,24]. In general, there are two different approaches, ''grafting to'' and ''grafting from'', for the modification of the surface of inorganic materials by organic polymer layers [25,26].…”

Section: Introductionmentioning

confidence: 99%

Grafting of silica with a hydrophilic triol acrylamide polymer via surface‐initiated “grafting from” method for hydrophilic‐interaction chromatography

Peng

Yuan

2011

J of Separation Science

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“…Chiral recognition of optically active polymers has been utilized in various forms of catalytic and separation chemistry. For example, one of the generally function of chiral polymers is the use as chiral stationary phase in high-performance liquid chromatography (HPLC) for the separation of racemic mixtures [2,[34][35][36][37][38]. Optically active polymers were divided to three types: biopolymers, polymers prepared by almost completely isotactic polymerization by modification of naturally occurring polymer backbones such as polysaccharides and synthetic polymers [2].…”

Section: Introductionmentioning

confidence: 99%

Advances in synthetic optically active condensation polymers - A review

Mallakpour

Zadehnazari²,

Iran³

2011

Express Polym. Lett.

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Abstract. The study of optically active polymers is a very active research field, and these materials have exhibited a number of interesting properties. Much of the attention in chiral polymers results from the potential of these materials for several specialized utilizations that are chiral matrices for asymmetric synthesis, chiral stationary phases for the separation of racemic mixtures, synthetic molecular receptors and chiral liquid crystals for ferroelectric and nonlinear optical applications. Recently, highly efficient methodologies and catalysts have been developed to synthesize various kinds of optically active compounds. Some of them can be applied to chiral polymer synthesis. In a few synthetic approaches for optically active polymers, chiral monomer polymerization has essential advantages in applicability of monomer, apart from both asymmetric polymerization of achiral or prochiral monomers and enantioselective polymerization of a racemic monomer mixture. The following are the up to date successful approaches to the chiral synthetic polymers by condensation polymerization reaction of chiral monomers.

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“…The effectiveness of such designs has been proven by many studies on chiral recognition by polymers bearing both chiral cyclic structures and functional groups for intermolecular interactions. [18][19][20][21] For example, stationary phases based on poly(trans-1,2-cyclohexanediyl-bisacrylamide), 19 which has a dichiral cyclic structure with restricted configuration, can separate many enantiomers. Accordingly, we evaluated the chiral induction with poly(1) consisting of units containing a chiral bicyclic structure and two amide groups by nuclear magnetic resonance (NMR) and CD spectroscopic measurements.…”

Section: Introductionmentioning

confidence: 99%

Chiral interaction between aromatic aldehydes and a polymer bearing large chiral rings obtained by cyclopolymerization of bisacrylamide

Ochiai

Ito

Endō

2009

Polym J

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This paper describes the investigation of an interaction between chiral induction behavior and a chiral polymer obtained by cyclopolymerization of a bisacrylamide (1) prepared from a-pinene and acrylonitrile. Poly(1) can interact with aromatic aldehydes, as confirmed by infrared (IR), circular dichroism (CD), diffusion-ordered nuclear magnetic resonance spectroscopy (DOSY) and 1-D nuclear Overhauser effect difference (1-D NOE) measurements. The observed induced CD demonstrates that the chiral framework of poly(1) forced aldehydes to remain in chiral environments. IR, DOSY and 1-D NOE measurements on mixtures of poly (1) Keywords: chiral interaction; cyclopolymerization; radical polymerization INTRODUCTION Chiral polymers have been used as stationary phases for chiral separation 1-10 and as templates for asymmetric reactions. 11-15 To achieve high performance with a chiral polymer, the polymer needs appropriate functional groups and a rigid structure. As a candidate, we designed a chiral polyacrylamide prepared through cyclopolymerization of a chiral bisacrylamide (1) (Scheme 1). 16 The monomer can easily be prepared by a one-step reaction of a-pinene and acrylonitrile. 17 The cyclopolymerization proceeds through the formation of 10-or 11-membered chiral rings. Although the structure of the rings has not been clarified completely by spectroscopic analyses, computational calculation suggested that the 11-membered ring formations are significantly predominant over 10-membered ring formations because of steric hindrance and the stability of propagating radicals. The details will be described elsewhere. In spite of the typically unfavorable large ring formation, this cyclopolymerization can yield soluble polymers bearing the desired cyclic units in quantitative yields. The selectivity of the cyclopolymerization without branching was confirmed by matrix-assisted laser desorption-ionization time of flight mass spectroscopy analysis of poly(1) obtained by reversible additionfragmentation chain transfer (RAFT) polymerization, indicating that poly(1) has only one initiating and terminating group originating from the chain transfer agent. The circular dichroism (CD) spectra of the resulting polymers show Cotton effects originating from the amide moieties in chiral environments and suggest the potential application of poly(1) as a chiral polymer. The chiral rings in poly(1) contain

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Chromatographic evaluation of poly (trans-1,2-cyclohexanediyl-bis acrylamide) as a chiral stationary phase for HPLC

Cited by 41 publications

References 27 publications

Grafting of silica with a hydrophilic triol acrylamide polymer via surface‐initiated “grafting from” method for hydrophilic‐interaction chromatography

Grafting of silica with a hydrophilic triol acrylamide polymer via surface‐initiated “grafting from” method for hydrophilic‐interaction chromatography

Advances in synthetic optically active condensation polymers - A review

Chiral interaction between aromatic aldehydes and a polymer bearing large chiral rings obtained by cyclopolymerization of bisacrylamide

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