A catechol receptor model by macrocyclic polyamines

Kimura, Eiichi; Watanabe, Asuka; Kodama, Mutsuo

doi:10.1021/ja00345a066

Cited by 53 publications

(17 citation statements)

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“…Figure 3 shows the anionic responses to phenol (14) at pH 6, observed for liquid membranes 1 -5 based on lipophilic macrocyclic polyamine 1 and simple aliphatic monoamines 2 -5, respectively, despite that 14 (pK a 9.99) 20 exists almost exclusively in its undissociated, neutral form in the aqueous solution bulk at the experimental pH. The strongest response was observed for membrane 2 based on tri(decyl)amine (2). The slopes of the potentiometric response curves in the concentration range of 10 -3 -10 -2 M 14 were ca.…”

Section: Potentiometric Response Behaviors Of Membranes Based On Alipmentioning

confidence: 98%

“…Based on the findings of Kimura et al 2 that a macrocyclic polyamine forms complexes with neutral phenols in aqueous solutions, we previously examined potentiometric responses to phenols by a PVC matrix liquid membrane based on lipophilic macrocyclic pentaamine 1, and found that the membrane exhibits anionic responses to undissociated, neutral phenols. 3,4 This response behavior is quite similar to that observed for PVC matrix liquid membranes based on quaternary ammonium or phosphonium salts.…”

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A Variety of Lipophilic Amines Incorporated in Liquid Membranes Exhibit Potentiometric Responses to Neutral Phenols

et al. 1998

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In a preceding paper 1 we reported on a systematic study of potentiometric responses to neutral phenols (ArOH) by poly(vinyl chloride) (PVC) matrix liquid membranes based on quaternary ammonium or phosphonium salts (Q + X -), and proposed a new model for the observed anionic responses. In this model, the decrease in the amount of Q + and X -that are chargeseparated across the membrane interface is explained on the basis of the following two processes: (i) Complexation of Q + X -and the extracted ArOH, leading to a net movement of anionic species (X -) from the aqueous to the membrane phase. (ii) Proton dissociation of the complexed ArOH and concomitant ejection of HX into the aqueous phase, involving a net movement of cationic species (H + ) from the membrane to the aqueous phase. A theoretical treatment based on the above model reproduced the potentiometric response behaviors for undissociated phenols. This model was further supported by optical second harmonic generation (SHG), which enabled a direct observation of the processes occurring at the interface of a liquid membrane and an aqueous solution.Based on the findings of Kimura et al.2 that a macrocyclic polyamine forms complexes with neutral phenols in aqueous solutions, we previously examined potentiometric responses to phenols by a PVC matrix liquid membrane based on lipophilic macrocyclic pentaamine 1, and found that the membrane exhibits anionic responses to undissociated, neutral phenols.3,4 This response behavior is quite similar to that observed for PVC matrix liquid membranes based on quaternary ammonium or phosphonium salts. A variety of lipophilic amines incorporated in PVC matrix liquid membranes exhibited anionic potentiometric responses to phenolic compounds at the pH conditions under which the phenols exist mainly or exclusively in their undissociated, neutral forms. The examined lipophilic amines include a macrocyclic pentaamine, tri(decyl)amine, 4,7-diphenyl-1,10-phenanthroline (bathophenanthroline), 4-octadecylpyridine, and sapphyrin. The potentiometric selectivities of the membranes based on lipophilic aliphatic amines (B) reflected the acidity (hydrogen bond donor activity) and lipophilicity (extractability) of the phenols (ArOH), similarly as membranes based on lipophilic quaternary ammonium salts (Q + X -). The anionic responses were explained on the basis of a decrease in the charge separation of protonated amines (BH + ) and their counteranions (X -) across the membrane interface. Possible processes leading to a decrease in the charge separation between BH + and X -are (i) complexation between ArOH and BH + X -, followed by proton dissociation and ejection of HX into the aqueous phase, as well as (ii) complexation between ArOH and B. The membrane based on sapphyrin showed a high potentiometric selectivity to catechol, possibly due to geometrical discrimination of the ortho dihydroxy structure of catechol by the nitrogen(s) on the rigid macrocyclic structure of sapphyrin.

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Section: Potentiometric Response Behaviors Of Membranes Based On Alipmentioning

confidence: 98%

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confidence: 99%

A Variety of Lipophilic Amines Incorporated in Liquid Membranes Exhibit Potentiometric Responses to Neutral Phenols

et al. 1998

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“…Based on the ®ndings of Kimura et al [9] that macrocyclic polyamine forms stable complexes with neutral catecholic compounds with loss of H in neutral pH aqueous solutions, Umezawa et al have developed a potentiometric sensor for determination of neutral phenols [10±13]. They have found that liquid membranes incorporated with lipophilic polyamines are able to generate a selective anionic response in the presence of undissociated phenol derivatives.…”

Section: Introductionmentioning

confidence: 99%

Influence of Substituents in Nitrogen Atoms in Macrocyclic Polyamine Incorporated into Poly(vinyl chloride) Matrix Liquid Membrane on Its Potentiometric Response to Neutral Phenols

et al. 2000

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Here we present the results of a study on the generation of the negative potentiometric response of solvent polymeric membranes based on macrocyclic ditopic hexaamines in the presence of neutral dihydroxybenzene isomers. The pH‐SEM profiles of the membranes investigated demonstrate a high affinity for proton uptake from the aqueous solution by host polyamine molecules. The substituents of the amine nitrogen atoms in host molecules strongly influence on the potentiometric anionic signal generation of membranes with hexaamine towards neutral dihydroxybenzenes. The possible mechanism of signal generation is discussed.

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“…In contrast, k increased with an increase in ACN% for 1,2-benzenediol over this range. This result could be attributed to the fact that the o-dihydroxy groups of 1,2-benzenediol might be a good donor to macrocyclic polyamine as reported by Kimura et al [29], and could exert retardation on the migration of 1,2-benzenediol while two hydroxyl groups of 1,4-benzenediol and 1,3-benzenediol are far from each other and they could not interact effectively with macrocyclic polyamines. Therefore, as the further increase in ACN %, this interaction eventually prevailed over the reduced RP chromatographic interaction and dominated the retention process for 1,2-benzenediol.…”

Section: Electrochromatographic Performance On the Monolithic Columnmentioning

confidence: 87%

Macrocyclic polyamine‐modified poly(glycidyl methacrylate‐co‐ethylene dimethacrylate) monolith for capillary electrochromatography

Tian¹,

Fang-Xing²,

Yang³

et al. 2008

Electrophoresis

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Macrocyclic polyamine-modified poly(glycidyl methacrylate-co-ethylene dimethacrylate) monolith for capillary electrochromatography 1,4,10,13,,17-dione (macrocyclic polyamine)-modified polymer-based monolithic column for CEC was prepared by ring opening reaction of epoxide groups from poly(glycidyl methacrylate-co-ethylene dimethacrylate) (GMA-co-EDMA) monolith with macrocyclic polyamine. Conditions such as reaction time and concentration of macrocyclic polyamine for the modification reaction were optimized to generate substantial EOF and enough chromatographic interactions. Anodic EOF was observed in the pH range of 2.0-8.0 studied due to the protonation of macrcyclic polyamine at the surface of the monolith. Morphology of the monolithic column was examined by SEM and the incorporation of macrocyclic polyamine to the poly(GMA-co-EDMA) monolith was characterized by infrared (IR) spectra. Successful separation of inorganic anions, isomeric benzenediols, and benzoic acid derivatives on the monolithic column was achieved for CEC. In addition to hydrophobic interaction, hydrogen bonding and electrostatic interaction played a significant role in the separation process.

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A catechol receptor model by macrocyclic polyamines

Cited by 53 publications

References 1 publication

A Variety of Lipophilic Amines Incorporated in Liquid Membranes Exhibit Potentiometric Responses to Neutral Phenols

A Variety of Lipophilic Amines Incorporated in Liquid Membranes Exhibit Potentiometric Responses to Neutral Phenols

Influence of Substituents in Nitrogen Atoms in Macrocyclic Polyamine Incorporated into Poly(vinyl chloride) Matrix Liquid Membrane on Its Potentiometric Response to Neutral Phenols

Macrocyclic polyamine‐modified poly(glycidyl methacrylate‐co‐ethylene dimethacrylate) monolith for capillary electrochromatography

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