Semiconducting materials from oxidative coupling of phenylenediamines under various acidic conditions

Bláha, Michal; Morávková, Zuzana; Humpolíček, Petr; Stejskal, Jaroslav

doi:10.1016/j.matchemphys.2017.11.007

Cited by 19 publications

(11 citation statements)

References 93 publications

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“…The oxidation of aromatic amines, especially o‐phenylenediamine (OPD), has already been utilized for various applications such as detection of metal ions, preparation of conducting polymers, pesticides and dyes . OPD is a colorless, nonfluorescent compound which can be oxidized by molecular oxygen or hydrogen peroxide in the presence of metal ions, forming 2,3–diaminophenazine (DAP) as the main oxidation product (Equation 1)…”

Section: Introductionmentioning

confidence: 99%

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂

Vetr

Moradi‐Shoeili

Özkâr

2018

Applied Organom Chemis

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Metal ferrites nanocrystallites, MFe2O4 (M = Mn, Co, Ni, Zn) were prepared by coprecipitation method and characterized by a combination of physico‐chemical and spectroscopic techniques. MFe2O4 nanoparticles having particle size in the range 10–35 nm were tested as catalysts in the oxidation of o‐phenylenediamine (OPD) to 2,3–diaminophenazine (DAP) using hydrogen peroxide as oxidant at room temperature. Kinetic data was collected for the catalytic oxidation of OPD to DAP by monitoring the UV–vis absorbance at 415 nm and fit well to the Michaelis–Menten model yielding kinetic parameters Km (Michaelis–Menten constant) and Vmax (maximum rate of reaction). MnFe2O4 nanoparticles provide the highest catalytic activity in the oxidation of OPD to DAP at room temperature. A colorimetric method was developed based on the MnFe2O4/OPD system for the detection of H2O2 in reaction solution. The method has a detection limit of 30 μM for H2O2 and wide linear range.

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Section: Introductionmentioning

confidence: 99%

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂

Vetr

Moradi‐Shoeili

Özkâr

2018

Applied Organom Chemis

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“…In order to identify the interactions between EG and PPD, we characterized the UV–Visible absorption spectra of PPD and EG‐PPD (Figure 3(b)). According to the UV–vis spectrum, there is a strong peak in PPD spectrum at 243 nm (which is the transition of π−π*) 32 and a main peak at 255 nm in EG‐PPD spectrum which is shifted compared to PPD. This could be ascribed to the π‐π stacking interactions between PPD and EG 33 .…”

Section: Resultsmentioning

confidence: 99%

High‐thermal conductivities of epoxy composites via p‐phenylenediamine interfacial modification and process intensification

Bao

Cui

et al. 2021

J of Applied Polymer Sci

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High loadings of fillers are usually needed to achieve high‐thermal conductivity (TC) of polymer‐based composites, which inevitably sacrifices processability and meanwhile causes high‐cost. Therefore, it is of great significance to achieve high‐TC composites under low‐filler loading. Here, a novel p‐phenylenediamine (PPD) modified expanded graphite (EG‐PPD)/epoxy (EP) composite with high TC and low‐filler content was successfully prepared via pre‐dispersion and vacuum assisted mixing strategy. With the improved interfacial compatibility between EG and EP by PPD, the prepared EG‐PPD/EP composite exhibited excellent thermal management performance, resulting in the TC of which reached 4.00 W·m−1·K−1 with only 10 wt% (5.59 vol%) of EG‐PPD, which is approximately 19 times higher than that of pure EP. Meantime, the interface thermal resistance of EG‐PPD/EP composite between EG‐PPD and EP is reduced by 33% compared with EG/EP composite. This composite with excellent TC property is expected to be used in thermal management field.

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“…Their low intensity indicates a significant decrease in the proportion of 1,3-substituted phenyl rings in the polymer as compared to the monomer. The new broad intense band at 830 cm −1 in the polymer spectrum indicates the presence of a large number of 1,2,4,5-substituted aromatic rings in the polymer, resulting from cyclization reactions [37,76,77].…”

Section: The Effect Of Substituent Types In Arylamine Groups Of the Quinone Ring On The Oxidation Reaction Rate And The Structure Of The mentioning

confidence: 99%

“…When a substituent is in the orthoposition, this monomer gives a polymer with a molecular weight of 2 × 10 3 g/mol and electrical conductivity up to 10 −3 S•cm −1 . Amino and hydroxy groups in the aromatic ring activate the oxidative polymerization, but, during the oxidation, phenylenediamines and aminophenols themselves form either low molecular weight soluble products or crosslinked polycyclic structures [28,[34][35][36][37][38][39]. The electrical conductivity of polyphenylenediamines was in the range of 10 −4 -10 −6 S•cm −1 [34,36].…”

Section: Introductionmentioning

confidence: 99%

Peculiarities of Oxidative Polymerization of Diarylaminodichlorobenzoquinones

et al. 2021

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New oxidative polymerization monomers—diarylaminodichlorobenzoquinones were synthesised by alkylating aniline, m-phenylenediamine and methanilic acid with chloranil. Oxidative polymerization of diarylaminodichlorobenzoquinones was studied for the first time in relation to the concentration of the monomer, acid, and oxidant/monomer ratio. It was found that the synthesized monomers are highly active in the polymerization reaction, and the oxidation rate grows with the increase in the acid concentration. Only one arylamine group is involved in the polymerization reaction. The optimal oxidant/monomer ratio is stoichiometric for one arylamine group, despite the bifunctionality of the monomers. It was shown that the type of the substituent in the aniline ring (electron donor or electron acceptor) determines the growth of the polymer chain and the structure of the resulting conjugated polymers. A mechanism for the formation of active polymerization centers for diarylaminodichlorobenzoquinones was proposed. FTIR-, NMR-, X-ray photoelectron spectroscopy, and SEM were used to identify the structure of the synthesized monomers and polymers. The obtained polymers have an amorphous structure and a loose globular morphology. The frequency dependence of the electrical conductivity was studied.

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Semiconducting materials from oxidative coupling of phenylenediamines under various acidic conditions

Cited by 19 publications

References 93 publications

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂

High‐thermal conductivities of epoxy composites via p‐phenylenediamine interfacial modification and process intensification

Peculiarities of Oxidative Polymerization of Diarylaminodichlorobenzoquinones

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Semiconducting materials from oxidative coupling of phenylenediamines under various acidic conditions

Cited by 19 publications

References 93 publications

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe2O4 (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H2O2

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe2O4 (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H2O2

High‐thermal conductivities of epoxy composites via p‐phenylenediamine interfacial modification and process intensification

Peculiarities of Oxidative Polymerization of Diarylaminodichlorobenzoquinones

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Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂

Oxidation of o‐phenylenediamine to 2,3‐diaminophenazine in the presence of cubic ferrites MFe₂O₄ (M = Mn, Co, Ni, Zn) and the application in colorimetric detection of H₂O₂