Aminopropyl-Silica Gel Modified with Nickel(II)-Phthalocyanine for Separation of .PI.-Electron Rich Compounds by High Performance Liquid Chromatography.

Mifune, Masaki; Onoda, Midori; Takatsuki, Tsutomu; Kanai, Takemine; Iwado, Akimasa; Motohashi, Noriko; Haginaka, Jun; Saito, Yutaka

doi:10.1248/cpb.47.346

Cited by 15 publications

(10 citation statements)

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“…14,15) It has also been known that many substances from environmental pollutants and mutagens are plane-type molecules having p electrons. The planar recognition ability of the M-PCS D column was evaluated using, as a sample, pairs of substances having different planarity, A (biphenylene/biphenyl), B (fluorene/ diphenylmethane) and C (triphenylene/o-terphenyl).…”

Section: ® -Columnsmentioning

confidence: 99%

“…8,9) On the other hand, it has been reported that a silica-based M-PCS D column, wherein metal phthalocyanine sulfonic acid derivative (M-PCS) is immobilized on silica gels, and of which separation mechanism is principally based on the p-p interaction in a polar solvent (e.g., methanol-water system), is useful for separations of PAHs. [13][14][15][16] In the M-PCS D , metal phthalocyanine is immobilized on silica gels in a horizontal manner, and the immobilization makes greater planar recognition ability than that of the PYE column ® . 14,15) Generally, PAHs having many aromatic rings are slightly/poorly soluble in a polar solvent, and, therefore, PAHs are usually extracted with a non-polar eluent before applying to HPLC.…”

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“…[13][14][15][16] In the M-PCS D , metal phthalocyanine is immobilized on silica gels in a horizontal manner, and the immobilization makes greater planar recognition ability than that of the PYE column ® . 14,15) Generally, PAHs having many aromatic rings are slightly/poorly soluble in a polar solvent, and, therefore, PAHs are usually extracted with a non-polar eluent before applying to HPLC. Thus, a comparative study has been carried out to elucidate the mechanism underlying the separation of PAHs with the M-PCS D columns and other columns including the PYE ® column in a non-polar eluent, such as n-hexane.…”

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HPLC Retention Behavior of Poly-Aromatic-Hydrocarbons on Aminopropyl Silica Gels Modified with Cu(II)- and Ni(II)-Phthalocyanine Derivatives in Non-polar Eluent

Akizawa

Kitamura

Yamane

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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were purchased from Aldrich, U.S.A. Phthalocyanine (H 2 -PC) was obtained from Tokyo Kasei, Japan. As a supports, Develosil NH 2 -5 ® (hereinafter, referred to as "Dev", Nomura Kagaku, Japan) which is a spherical aminopropyl silica gels (particle size, 5 mm; specific surface area, 350 m 2 /g; average pore size, 120 Å) was used. As an eluent, n-hexane for HPLC (Nacalai Tesque, Japan) was mainly used, and as a solvent for packing M-PCS D , slurry solvent A Conc. (Chemco Scientific, Japan) was used. The commercially available PYE ® column and NPE ® (nitro-phenylethyl silica gels) column (Nacalai Tesque, Japan) were used for comparison to elucidate the underlying separation mechanism of the M-PCS D column. M-PCS D ColumnsMetal-phthalocyanine tetrasulfonyl chloride (MPCSCl: MϭH 2 , Ni 2ϩ and Cu 2ϩ , see Fig. 1) was synthesized from H 2 -PC, Cu-PC and Ni-PC as described by Nadler et al.17) The resultant Ni-PCSCl (5.6 mg), Cu-PCSCl (5.6 mg) or H 2 -PCSCl (5.3 mg) was each dissolved in dioxane (150 ml), following the addition of Dev (1.5 g), and was refluxed for 2 h. After standing to cool, M-PCS D was separated by filtration, and washed with methanol (100 ml), dried thoroughly in vacuo over diphosphorous pentoxide. The M-PCS D column was then prepared by packing the obtained M-PCS D into a stainless-steel column (f4.6ϫ150 mm) for HPLC by a conventional slurry packing method. Throughout the process, the filtrate and the like were clear and colorless, and the absorption spectra thereof were free from characteristic absorption band(s) of M-PCSCls or M-PCSs. From these evidences, it was concluded that M-PCS was completely immobilized on silica gels. The amount of M-PCS immobilized was also estimated from the absorption spectrum of the initial M-PCS solution in dioxane.

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Section: ® -Columnsmentioning

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HPLC Retention Behavior of Poly-Aromatic-Hydrocarbons on Aminopropyl Silica Gels Modified with Cu(II)- and Ni(II)-Phthalocyanine Derivatives in Non-polar Eluent

Akizawa

Kitamura

Yamane

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Chemically modified silicas are used extensively in many scientific and technological applications, for example, as HPLC bonded phases for specific separations (2,3,(9)(10)(11), supports for catalysts in specific organic reactions (12), supports for microorganisms (13) and pesticides (14), and the immobilization of humic acid (15) and the extraction of metallic cations from aqueous and nonaqueous solvents by forming immobilized metallic complexes, which present variable composition and distorted geometries (16). This last application has been extensively studied 1 To whom correspondence should be addressed.…”

Section: Introductionmentioning

confidence: 99%

New Factorial Designs to Evaluate Chemisorption of Divalent Metals on Aminated Silicas

Cestari

Vieira

Nascimento

et al. 2001

Journal of Colloid and Interface Science

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“…Cu 2+ and Ni2+-phthalocyanine [14] derivatives, as well as metal porphyrins [15], have been recently immobilized on silica gel and used to separate polycydic aromatic hydrocarbons (PAHs).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new organometallic complexes bonded stationary phases for high-performance liquid chromatography

Bordelanne

Delville

Félix³

et al. 2000

Chromatographia

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KeyWordsColumn liquid chromatography Synthesis of bonded stationary phases Organometallic complexes Charge-transfer interactions PAHs SummaryThe preparation, characterization and potential liquid chromatographic applications of various organometallic iron complexes silica stationary phases are presented. These new supports are synthesized by covalently linking ferrocene, as well as some of its cationic derivatives, to appropriately derivatized silica support matrices. These columns exhibit moderate to high selectivity towards the separation of polycyclic aromatic hydrocarbons (PAHs). A charge transfer retention mechanism has been proposed. A comparison with a reference stationary phase, 3,5-dinitrobenzamide (DNB), to quantify the acceptor power of the new stationary bonded phases, is also reported. Finally the effect of varying the derivatives of the bonded metallocene on PAHs retention is discussed.

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Aminopropyl-Silica Gel Modified with Nickel(II)-Phthalocyanine for Separation of .PI.-Electron Rich Compounds by High Performance Liquid Chromatography.

Cited by 15 publications

References 1 publication

HPLC Retention Behavior of Poly-Aromatic-Hydrocarbons on Aminopropyl Silica Gels Modified with Cu(II)- and Ni(II)-Phthalocyanine Derivatives in Non-polar Eluent

HPLC Retention Behavior of Poly-Aromatic-Hydrocarbons on Aminopropyl Silica Gels Modified with Cu(II)- and Ni(II)-Phthalocyanine Derivatives in Non-polar Eluent

New Factorial Designs to Evaluate Chemisorption of Divalent Metals on Aminated Silicas

Synthesis and characterization of new organometallic complexes bonded stationary phases for high-performance liquid chromatography

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