Electrochemical preparation of a ladder polymer containing phenazine rings

Chiba, Kazuyuki; Ohsaka, Takeo; Ohnuki, Yoshio; Oyama, Noboru

doi:10.1016/0022-0728(87)85034-9

Cited by 196 publications

(145 citation statements)

References 20 publications

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“…In addition, the electrochemical response obtained for 2,3-DAP resembles to those obtained for m-aminophenol [6] in the same conditions, suggesting that the oxidation of 2,3-DAP could also produce a crosslinked or a polyphenol-like material (Scheme 1). However, 2,3-DAP could also be seen as a o-phenylenediamine derivative and Po-PD is a ladder polymer with cyclic structure [46] like poly(o-aminophenol) [9,12]. Indeed, Del Valle et al have proposed that poly(2,3-DAP), produced in dry acetonitrile, has a ladder structure similar to Po-PD, with the hydroxyl group linked to the ladder backbone [48].…”

Section: Methodsmentioning

confidence: 99%

“…m-Phenylenediamine polymers could present two structures including rigid rod-like ladder or network type, depending on the coupling orientation in the m-PD monomer [35,42] [43][44][45] to form an electroactive film. The poly(o-phenylenediamine (Po-PD) is a ladder polymer [46] with structure and properties closely related to those of poly(o-aminophenol) [9,12]. Barbero et al reported that the global reaction rate of o-PD polymerization is faster than o-AP polimerization [12].…”

Section: Introductionmentioning

confidence: 99%

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Spectroelectrochemical study of the oxidation of diaminophenols on platinum electrodes in acidic medium

Salavagione

Arias

Garcés

et al. 2005

Electrochimica Acta

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The electrochemical oxidation of 2,3-2,4-and 2,5-diaminophenol, on platinum electrode, in acid medium was studied using cyclic voltammetry, in situ UV-vis and in situ FTIR spectroscopies. The spectroscopic data indicates that 2,4-diaminophenol suffers hydrolysis giving the formation of 2-amino-hydroquinone/2-amino-p-benzoquinone in solution. The oxidation mechanism of 2,5-diaminophenol is similar to the p-phenylenediamine giving 2-hydroxy-p-benzoquinoneimine and its hydrolysis product, 2-hydroxy-p-benzoquinone. The electrochemical results suggest that 2,3-diaminophenol generates a non-electroactive polymeric material on the electrode surface.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Spectroelectrochemical study of the oxidation of diaminophenols on platinum electrodes in acidic medium

Salavagione

Arias

Garcés

et al. 2005

Electrochimica Acta

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“…Effect of PPD polymerization potential on the selectivity of Pt D /PPD-BSA The structure of PPD films and their mechanisms of formation are known to be complex, and have been studied in some detail by many authors [34][35][36][37][38][39][40][41][42]. The properties of PPD have been suggested to depend mainly on the conditions of the polymerization, such as pH, electrolyte composition, temperature and the applied potential.…”

Section: Pt D /Nafion/pei/gluox/ppd-bsamentioning

confidence: 99%

Highly selective and stable microdisc biosensors for l-glutamate monitoring

Govindarajan

McNeil

Lowry

et al. 2013

Sensors and Actuators B: Chemical

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a b s t r a c tGlutamate mediates most of the excitatory synaptic transmission in the brain, and its abnormal regulation is considered a key factor underlying the appearance and progression of many neurodegenerative and psychiatric diseases. In this work, a microdisc-based amperometric biosensor for glutamate detection with highly enhanced selectivity and good stability is proposed. The biosensor utilizes the enzyme glutamate oxidase which was dip-coated onto 125 m diameter platinum discs. To improve selectivity, phosphatidylethanolamine was pre-coated prior to enzyme deposition, and electropolymerization of o-phenylenediamine was performed to entrap the enzyme within a polymer matrix. A variety of coating configurations were tested in order to optimize biosensor performance. For stability measurements, biosensors were biased continuously and calibration curves calculated each day for a period of 5-6 days. The optimized biosensors exhibited very high sensitivity (71 ± 1 mA M −1 cm −2 ), low detection limit of ∼2.5 M glutamate, selectivity (over 87% against ascorbic acid), very good temporal stability during continuous use, and a response time of <5 s. These biosensors are therefore good candidates for further development as devices for continuous monitoring during traumatic brain injury or neurosurgery.

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“…On the contrary, it is well documented that o-aminophenol can be electrochemically polymerized in acidic medium to yield an electroactive polymeric material that shows phenoxazine ladder structures [3,6]. It was also suggested that the products formed upon oaminophenol electrochemical oxidation depend on the pH of the polymerization solution [7] although it is worth noting that similar structure and properties can be obtained regardless of the polymerization method employed, either chemical or electrochemical [1].…”

Section: Introductionmentioning

confidence: 99%

The chemical and electrochemical oxidative polymerization of 2-amino-4-tert-butylphenol

Abidi

López-Bernabéu

Huerta

et al. 2016

Electrochimica Acta

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Poly(2-amino-4-tert-butylphenol), poly(2A-4TBP), was synthesized from monomer aqueous solution using either electrochemical or chemical oxidation procedures. Several spectroscopic characterization techniques were employed to gain information on the chemical structure and redox behavior of the obtained materials. It was found that the chemical polymerization product could be described as an oligomer mixture containing up to 16 monomer units. In parallel to other polymers derived from o-aminophenol, phenoxazine rings constitute also the basic structure of poly(2A-4TBP). In addition, the occurrence of N-N couplings, which are favored by the presence of the voluminous tert-butyl substituent, seems also relevant. No significant structural differences were found between the chemically or electrochemically synthesized materials.

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Electrochemical preparation of a ladder polymer containing phenazine rings

Cited by 196 publications

References 20 publications

Spectroelectrochemical study of the oxidation of diaminophenols on platinum electrodes in acidic medium

Spectroelectrochemical study of the oxidation of diaminophenols on platinum electrodes in acidic medium

Highly selective and stable microdisc biosensors for l-glutamate monitoring

The chemical and electrochemical oxidative polymerization of 2-amino-4-tert-butylphenol

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