Molecular Length Recognition of Polyaromatics Using Lipid Membrane Analogue-Immobilized Silica Gels

Ihara, Hirotaka; Fukumoto, Takanori; Hirayama, Chuichi

doi:10.2116/analsci.9.711

Cited by 17 publications

(2 citation statements)

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“…This peak was attributed to a crystallineto-isotropic phase transition based on the octadecyl moiety [25]. Figure 3 indicates that the peak-top temperature decreases from 48 °C to 38 °C, with peak shape broadening.…”

Section: Evaluation Of Side-chain Orientation In Grafted Polymeric Phasementioning

confidence: 98%

Enhancement of Thermal Stability and Selectivity by Introducing Aminotriazine Comonomer to Poly(Octadecyl Acrylate)-Grafted Silica as Chromatography Matrix

et al. 2018

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This paper introduces a poly(octadecyl acrylate) (pODA)-based organic phase on silica, which is assisted by 2-vinyl-4,6-diamino-1,3,5-triazine (AT), for a chromatography stationary phase. The ODA-AT copolymer grafting onto silica surface was characterized by elemental analysis, FT-IR spectroscopy, scanning electron microscopy, thermo gravimetric analysis and differential scanning calorimeter (DSC). An endothermic peak top of the copolymer-grafted silica was increased to 46 • C from 38 • C, which was a peak top of pODA homopolymer. For high performance liquid chromatography (HPLC) application, the molecular selectivity increased with an increase in the AT contents of the ODA-AT copolymer as organic phase. The co-existence of an aminotriazine moiety in the copolymer promoted side-chain ordering of the poly(octadecyl) moiety, thus enhancing molecular planarity selectivity for PAHs in reversed-phase liquid chromatography.

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Section: Evaluation Of Side-chain Orientation In Grafted Polymeric Phasementioning

confidence: 98%

Enhancement of Thermal Stability and Selectivity by Introducing Aminotriazine Comonomer to Poly(Octadecyl Acrylate)-Grafted Silica as Chromatography Matrix

et al. 2018

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“…We have investigated the hybridization between silica gels and polymers [1][2][3][4][5][6][7][8][9][10] such as polystyrene, 1 poly(acrylonitrile), 6 and poly(methyl acrylate) 3 which were applied to separation. These polymers possess π-electrons to be used as a π-π interaction source and thus have been applied as packing materials for liquid chromatography with π-electron recognition.…”

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Polymer Effect on Molecular Recognition. Enhancement of Molecular-Shape Selectivity for Polycyclic Aromatic Hydrocarbons by Poly(acrylonitrile)

Takafuji

Dong

Goto

et al. 2002

Polym J

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ABSTRACT:Poly(acrylonitrile) immobilized onto porous silica (Sil-AN n ) was prepared to evaluate the effect of polymerization degree of poly(acrylonitrile) on selective interaction with polycyclic aromatic hydrocarbons. The HPLC using the packed column (Sil-AN n ) and an aqueous solution as a mobile phase showed higher selectivity for structural isomers of polycyclic aromatic hydrocarbons compared with simply cyanopropylated silica (Sil-CN) and alkylated silica (Sil-C 4 ). It was considered that silica-supported poly(acrylonitrile) recognized molecular aromaticity of π-electron containing compounds rather than molecular hydrophobicity. Furthermore, similar results were obtained in the selectivity towards geometrical isomers such as trans-and cis-stilbenes or triphenylene and o-terphenyl and structural isomers such as o-, m-, p-terphenyls. Also the separation factors increased with an increase in polymerization degree of AN n . This paper discusses that polymeric structures enhance the selectivity.KEY WORDS Polymer Grafting Silica / High Performance Liquid Chromatography (HPLC) / Multiple π-π Interactions / CN-π-to-benzene-π Interaction / Molecular Aromaticity / Geometrical Isomers / Structural Isomers / Specific behaviors of many polymers are based on their configurations and conformations. The chemical structures of monomer units and their arrangements influence on the conformational structures of polymer chain and then closely relate to their functions whose are carried out by multiple interactions through accumulation of their functional groups. In biological systems, there are many examples of protein polymers, the structures of which determine the biological functions. The molecular assemblies such as bio-membranes also show specific behaviors in bio-systems.On the other hand, synthetic polymers are used as many industrial materials such as films, fibers and adhesions. It is well-known that crystallinity and polymerization degree influence the properties of polymers. Many researchers have reported physical and chemical properties of polymers with functional groups in their main and side chains because it is important to mimic the functions of biopolymers using simply synthetic polymers. This will expand possible applications of polymers.We have investigated the hybridization between silica gels and polymers 1-10 such as polystyrene, 1 poly(acrylonitrile), 6 and poly(methyl acrylate) 3 which were applied to separation. These polymers possess π-electrons to be used as a π-π interaction source and thus have been applied as packing materials for liquid chromatography with π-electron recognition. As a re- † To whom correspondence should be addressed. sult, we have found that the polymer-immobilized silica showed much better selectivity for structural isomers of polycyclic aromatic hydrocarbons than the corresponding monomer-immobilized silica. In this paper, we wish to report the effects of polymerization degree of polymers on separation behavior of polycyclic aromatic hydrocarbons by using poly(acrylonitrile). ...

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A Facile and Specific Approach to New Liquid Chromatography Adsorbents Obtained by Ionic Self‐Assembly

Qiu

Mallik

Takafuji

et al. 2011

Chemistry A European J

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A new ionic-liquid monomer, 1-vinyl-3-octadecylimidazolium bromide ([C(18)VIm]Br), was prepared and polymerized on porous silica particles by means of a surface-initiated radical chain-transfer reaction. Further modification for functionalization was performed through the exchange of counteranions from bromide to methyl orange (MO). Two new silica-poly(octadecylimidazolium) (Sil-PImC(18)) hybrid materials (Sil-PImC(18)-Br and Sil-PImC(18)-MO) were synthesized and characterized by elemental analysis, thermogravimetric analysis, diffuse reflectance infrared Fourier transform spectroscopy (DRIFT), and solid-state (13)C CP/MAS NMR spectroscopy. Sil-PImC(18)-MO presented ultra-high shape selectivity for constrained isomers of polycyclic aromatic hydrocarbons (PAHs) both in reversed- and normal-phase HPLC when used as the stationary phase. Fundamental aspects of the molecular shape selectivity were evaluated by using Standard Reference Material (SRM) 869b; the column selectivity test mixture for liquid chromatography. The impact of this phase was also demonstrated by the separation of SRM 1647e (16 priority pollutant PAHs) and several steroid isomers. Enhanced selectivity could be explained by the highly oriented arrangement between the octadecylimidazolium chain and a rigid segment of MO. These findings may open a new window of research for the design of materials used in chromatographic supports, solid extraction, catalysis, and electrolytes by simple modifications of the counterions in the poly(ionic liquid) analogous phase.

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Molecular Length Recognition of Polyaromatics Using Lipid Membrane Analogue-Immobilized Silica Gels

Cited by 17 publications

References 1 publication

Enhancement of Thermal Stability and Selectivity by Introducing Aminotriazine Comonomer to Poly(Octadecyl Acrylate)-Grafted Silica as Chromatography Matrix

Enhancement of Thermal Stability and Selectivity by Introducing Aminotriazine Comonomer to Poly(Octadecyl Acrylate)-Grafted Silica as Chromatography Matrix

Polymer Effect on Molecular Recognition. Enhancement of Molecular-Shape Selectivity for Polycyclic Aromatic Hydrocarbons by Poly(acrylonitrile)

A Facile and Specific Approach to New Liquid Chromatography Adsorbents Obtained by Ionic Self‐Assembly

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