Electrosynthesis and characterization of poly(1,3-dimethoxybenzene)

Martínez, Y.; Hernández, Ricardo; Kalaji, M.; Márquez, Jairo; Márquez, O. P.

doi:10.1016/s0379-6779(98)80126-4

Cited by 58 publications

(7 citation statements)

References 24 publications

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“…The conductivity value obtained places this material in the semiconducting range. However, the values are two order of magnitude lower than that reported for the poly(1,3-dimethoxybenzene) [10]. This can be attributed to the steric hindrance of the alkoxy substituents and the residual metal ions of the catalytic oxidants.…”

Section: Optical and Electrical Propertiescontrasting

confidence: 55%

“…3, four peaks (d 99.02, 120.41, 135.06, and 156.51) appear in the aromatic region, related to the six aromatic carbon atoms of the polymer repeating unit. The concise peaks of 13 C-NMR spectrum indicated that in poly(1,3-DBB), the aromatic ring moieties linkage at meta-position, which agreed with the poly(1,3-DMB) by electrosynthesis in Bu 4 NBF 4 /CH 3 CN [10].…”

Section: Instrumentalsupporting

confidence: 54%

“…7, the appearance of P2 exhibits grains of irregular granular shape. That is different from the morphology of poly(1,3-DMB) synthesized via the electrochemical oxidation [10].…”

Section: Thermal and Morphological Propertiesmentioning

confidence: 57%

“…Poly(1,3-dimethoxybenzene) have been directly prepared from 1,3-dimethoxybenzene by electrochemical polymerization and oxidative coupling polymerization [10,11], while the material is insoluble in all common solvents. Oxidative coupling polymerization developed from Scholl reaction involves the coupling of aromatic nuclei by an oxidative process [12,13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of poly(1,3-dialkoxybenzene)s from facile solvent-free grinding oxidative coupling polymerization

Bai

Chen

Xu³

et al. 2011

Polym. Bull.

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Soluble conjugated aromatic poly(1,3-dialkoxybenzene)s were obtained in high yield up to 80% in 30 min by grinding 1,3-dialkoxybenzene with anhydrous FeCl 3 powder in a mortar at ambient and solvent-free condition. The polymers were characterized by FT-IR, 1 H-NMR, 13 C-NMR, and gel permeation chromatography. The structure of the aromatic rings linkage at meta-position was confirmed. Thermogravimetric analysis, UV-Vis, fluorescence spectroscopy, and four-probe a.c. technique were used to probe the thermal, optical, and electrical properties of the polymers. The polymers displayed high thermostability with the decomposition temperatures at about 382-388°C. The optical energy gap (E g ) of the polymers was 4.23 eV and electrical conductivity at room temperature was 10 -6 S cm -1 . The fluorescence curve of the polymers displayed the maximum at 344 nm in CH 2 Cl 2 solution. The morphology of the polymers was determined by X-ray diffraction and scanning electron microscope technique.

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Section: Optical and Electrical Propertiescontrasting

confidence: 55%

Section: Instrumentalsupporting

confidence: 54%

“…7, the appearance of P2 exhibits grains of irregular granular shape. That is different from the morphology of poly(1,3-DMB) synthesized via the electrochemical oxidation [10].…”

Section: Thermal and Morphological Propertiesmentioning

confidence: 57%

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of poly(1,3-dialkoxybenzene)s from facile solvent-free grinding oxidative coupling polymerization

Bai

Chen

Xu³

et al. 2011

Polym. Bull.

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“…Preparation of polymer films by oxidation and electropolymerization of aromatic compounds (aniline, phenol, benzene, and their derivatives) 1–6 and of heteroaromatic compounds (pyrrol, tiophene, and their derivatives) 7–11 has been widely used in electrode surface modification as a mean to obtain interesting electrode properties. The increasing development of new electrode materials has motivated the electropolymerization study of new organic molecules.…”

Section: Introductionmentioning

confidence: 99%

Prediction of reactive sites for the electropolymerization of p‐benzenesulfonic acid derivatives: Ab initio and experimental study

Nabais

Fartaria

Fernandes

et al. 2004

Int J of Quantum Chemistry

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ABSTRACT:A theoretical study of the electronic structure of some p-benzenesulfonic acid derivatives is carried out to explain the electrooxidation of these compounds, in particular the allyl ether p-benzenesulfonic acid, sodium salt electrooxidation, and electrode surface modification observed during electrochemical studies. The effects of the alkyl side chain and of the aromatic ring during electrooxidation are considered using the UHF and B3LYP levels of theory. The changes in monomer structure after removal of an electron are explained by the nodal structure of the highest occupied molecular orbital (HOMO), ␣ and ␤ single occupied molecular orbitals (SOMO) and by their energies. Apart from frontier molecular orbital theory, charge reaction control, which is expected to occur at higher oxidation potentials, is also discussed. The calculations indicate that the unpaired electron spin distribution and atomic charge variation in the radical cation is very sensitive to the nature of the alkyl side chain. In fact, this distribution reflects the electronic structure of these monomers related to their oxidability. It is shown that the removal of an electron is carried out by two competing mechanisms.

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Spectroelectrochemical Behaviour of 1,4‐Dimethoxypillar[5]arene (P5A) and its Monomer in Different Organic Solvents

et al. 2021

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This work is dedicated to Prof. Marcin Opałło on the occasion of his 65 th birthdayThe spectroelectrochemical response of the macrocyclic compound 1,4-dimethoxypillar[5]arene (P5A) and its monomer 1,4dimethoxybenzene was investigated using cyclic voltammetry combined with UV-Vis spectroscopy. The influence of three different aprotic solvents, acetonitrile, dichloromethane, and dichloroethane, as well as supporting electrolyte, on the anodic behaviour of P5A were studied and discussed. The results indicate that the donor-acceptor Lewis-type interactions be-tween tested compounds and the solvent molecules affect the oxidation processes and thus the formal potentials (E f ). In all solvents we see subsequent oxidation of P5A to P5A 5 + followed at higher potential by an irreversible oxidation to the corresponding quinone. The results also show that small amounts of water can significantly influence the redox behaviour of the P5A.

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Electrosynthesis and characterization of poly(1,3-dimethoxybenzene)

Cited by 58 publications

References 24 publications

Synthesis and properties of poly(1,3-dialkoxybenzene)s from facile solvent-free grinding oxidative coupling polymerization

Synthesis and properties of poly(1,3-dialkoxybenzene)s from facile solvent-free grinding oxidative coupling polymerization

Prediction of reactive sites for the electropolymerization of p‐benzenesulfonic acid derivatives: Ab initio and experimental study

Spectroelectrochemical Behaviour of 1,4‐Dimethoxypillar[5]arene (P5A) and its Monomer in Different Organic Solvents

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