Spectroscopic investigation on polymer films obtained by oxidation of o-phenylenediamine on platinum electrodes at different pHs

Losito, Ilario; Giglio, Elvira De; Cioffi, Nicola; Malitesta, Cosimino

doi:10.1039/b101626l

Cited by 82 publications

(103 citation statements)

References 36 publications

(39 reference statements)

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“…intensity at higher potentials show these vibrational modes are unequivocally related with the oxidized state of the polymer. In fact, the higher frequency band can be assigned to the C=C stretching vibration of quinoid rings, which is here more intense and shifted to lower wavenumbers than in Fig.3, whereas the 1190 cm -1 feature is attributed to a combination of quinoid C-N-C stretching and C-H in-plane bending [24,30,31]. The assignment of the 1280 cm -1 peak is uncertain but, according to previous literature data, it can be attributed to the persistence of persulfate ions which were employed as the oxidizing agent [32].…”

Section: Chemically Polymerized 2a-4tbpmentioning

confidence: 98%

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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Section: Chemically Polymerized 2a-4tbpmentioning

confidence: 98%

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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“…The secondary peak can be assigned to aromatic carbons bound to amine and to imine nitrogens. 9,43,45,46 The C 1s binding energy ͑BE͒ of these nitrogen functionalities has been reported not to be unambiguously distinguishable from those for carbon singly bound to oxygen groups, 45 but the low amount of oxygen detected in the survey spectrum ͑not shown͒ suggests that C-OH/C-O-C functionalities do not contribute significantly to the 285.9 eV peak. The N1s spectrum displays a broad peak contributed by three components at 398.0 ͑7.1%͒, 399.4 ͑61.6%͒, and 401.0 ͑31.3%͒ eV.…”

Section: D118mentioning

confidence: 99%

“…In fact, it has already been proposed that o-phenylenediamine can be electrochemically polymerized, yielding phenazine rings, thanks to the presence of two amino groups in ortho position. [41][42][43][44] A similar mechanism could act in the case of 2-adpa electropolymerization to give the corresponding ladder structure, as shown for the fully oxidized state in Scheme 3. An additional support to the hypothesis pointing to the formation of D119 Journal of The Electrochemical Society, 153 ͑7͒ D114-D122 ͑2006͒ D119 similar polymeric products from neutral red and 2-adpa can be found in the fact that the four-unit oligomer electrogenerated from o-phenylenediamine, which is known to contain phenazine units, shows a UV-visible spectrum quite similar to that displayed in Fig.…”

Section: D118mentioning

confidence: 99%

Synthesis and Characterization of Electroactive Films Deposited from Aniline Dimers

Cotarelo

Huerta

Quijada

et al. 2006

J. Electrochem. Soc.

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The electrochemical oxidation of the aniline dimers 2-aminodiphenylamine ͑2-adpa͒ and 4-aminodiphenylamine ͑4-adpa͒ has been performed in strongly acidic medium on platinum, graphite, and indium tin oxide electrodes. The resulting films have been characterized by a number of electrochemical, microscopic, and spectroscopic techniques in order to gain some insight on their respective chemical structures. Both poly͑2-adpa͒ and poly͑4-adpa͒ are electroactive species which differ significantly one from another. It was found that aged poly͑4-adpa͒ displayed electrochemical, morphologic and spectroscopic characteristics similar to those shown by polyaniline. On the contrary, poly͑2-adpa͒ is really a mixture of three oligomerization products. The two main oligomers contain both open-ring and cycled phenazine centers, although their chemical structures seem to differ in the cap-end of the chain growth. The third oligomer is a minor product which seems a highly symmetric macrocycle involving several 2-adpa molecules.

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“…The quantification of amines from the total nitrogen concentration can be difficult if other functional groups with similar N1s binding energies are present. Aldehydes like pentafluorobenzaldehyde [13,14] or trifluoromethylbenz aldehyde [15] were reported as derivatization agents for primary amino groups.…”

Section: Introductionmentioning

confidence: 99%

TFAA chemical derivatization and XPS. Analysis of OH and NHx polymers

Pippig

Sarghini

Holländer

et al. 2009

Surface & Interface Analysis

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The determination of functional groups on complex polymer surfaces by X-ray photoelectron spectroscopy (XPS) can be improved considerably by derivatization reactions. Simple polymers containing hydroxyl groups or amino groups were investigated as reference materials for the derivatization with trifluoroacetic anhydride (TFAA).Poly(vinyl alcohol) (PVA), poly(hydroxyethyl methacrylate) (PHEMA), poly(vinyl butyral) (PVB), poly(allylamine) (PAAm), and poly(diallyl amine) (PDAAm) were derivatized using TFAA and analyzed with XPS. Polyethylene (PE) was used as an independent external reference for the binding energy (BE). Applying this procedure, the BE scales of all measurements were referenced to the carbon atoms of PE. It was found that the BE of the CF 3 component in the C1s region is different when bonded as an acetate or as an amide. The CF 3 BE is also influenced by the density of these groups in the polymer molecule. In TFAA-PVA, where every second main chain carbon atom carries a trifluoroacetate (TFAc) group, the BE is 294.3 eV while in TFAA-PVB with only isolated groups, the BE is 293.6 eV. The BE of the CF 3 component in the trifluoroacetamides (TFAAms) prepared from PAAm and PDAAm was found to be 292.5 and 292.3 eV, respectively. Compared with the analog fluorine free compounds, the BE is shifted toward higher values also for the ester carbon atom, the amide carbon atom, and the carbon atom to which the ester or amide is bonded.The data suggest that the gas phase reaction of TFAA with a polymer surface is diffusion limited. The actual ester or amide formation is a fast reaction and runs as a wave into the surface.

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Spectroscopic investigation on polymer films obtained by oxidation of o-phenylenediamine on platinum electrodes at different pHs

Cited by 82 publications

References 36 publications

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

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

Synthesis and Characterization of Electroactive Films Deposited from Aniline Dimers

TFAA chemical derivatization and XPS. Analysis of OH and NHx polymers

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