Electrochemical polymerization and spectroscopic investigation of 2-methylindole

Udum, Yasemin Arslan; Düdükcü, Meltem; Köleli, Fatih

doi:10.1016/j.reactfunctpolym.2007.12.006

Cited by 20 publications

(11 citation statements)

References 19 publications

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“…7,8 Many intrinsic properties (for example, the polymerization mechanism) of bicyclic heterocyclic molecules are masked by their environment or by their interactions with it. 9,10 In this case, gas-phase data can provide a better understanding of the properties of indoles in the absence of perturbations due to their interactions with the surroundings.…”

Section: ■ Introductionmentioning

confidence: 99%

“…It has been shown that indole-coated surfaces have desirable properties such as selectivity, sensitivity, and stability . Thus, they have widespread applications compared to bare surfaces and can be used as selective electrodes, which are sensitive to various cationic and anionic inorganic species, as a biosensor for biological molecules, or as a protection of metallic surfaces against corrosion. , Many intrinsic properties (for example, the polymerization mechanism) of bicyclic heterocyclic molecules are masked by their environment or by their interactions with it. , In this case, gas-phase data can provide a better understanding of the properties of indoles in the absence of perturbations due to their interactions with the surroundings.…”

Section: Introductionmentioning

confidence: 99%

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Carbon and Nitrogen K-Edge NEXAFS Spectra of Indole, 2,3-Dihydro-7-azaindole, and 3-Formylindole

et al. 2021

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The near-edge X-ray absorption fine structure (NEXAFS) spectra of indole, 2,3-dihydro-7-azaindole, and 3-formylindole in the gas phase have been measured at the carbon and nitrogen K-edges. The spectral features have been interpreted based on density functional theory (DFT) calculations within the transition potential (TP) scheme, which is accurate enough for a general description of the measured C 1s NEXAFS spectra as well as for the assignment of the most relevant features. For the nitrogen K-edge, the agreement between experimental data and theoretical spectra calculated with TP-DFT was not quite satisfactory. This discrepancy was mainly attributed to the many-body effects associated with the excitation of the core electron, which are better described using the time-dependent density functional theory (TDDFT) with the range-separated hybrid functional CAM-B3LYP. An assignment of the measured N 1s NEXAFS spectral features has been proposed together with a complete description of the observed resonances. Intense transitions from core levels to unoccupied antibonding π* states as well as several transitions with mixed-valence/Rydberg or pure Rydberg character have been observed in the C and N K-edge spectra of all investigated indoles.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Carbon and Nitrogen K-Edge NEXAFS Spectra of Indole, 2,3-Dihydro-7-azaindole, and 3-Formylindole

et al. 2021

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“…More than 200 publications and reviews deal with PIn synthesis. The most common methods for producing this polyheterocycle and its derivatives include the electrochemical synthesis and chemical oxidation in the presence of metal complex catalysts. − However, these synthetic methods are not preferred because of their low yields, the loss of redox properties after deposition on electrodes during the polymerization process, the need for expensive materials, the high sensitivity of the catalysts to oxygen, and the complexity of the procedure required to isolate the target products. − Therefore, the search for an efficient way for synthesizing PIn remains a relevant issue.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Physicochemical Properties of Poly(2-ethyl-3-methylindole)

et al. 2020

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Intramolecular acid-catalyzed cyclization was suggested for the first time for a polyaniline derivative, namely, poly[2-(2-chloro-1-methylbut-2-en-1-yl)aniline] (PClPA), to give hitherto unknown poly(2-ethyl-3-methylindole) (2E3MPIn) in a high yield (81%). This is the first example of synthesizing a polymer of the indole series with 1,5-addition of monomeric units that are incorporated into the polymer structure. The physicochemical properties of the new polymer were studied. Its structure was confirmed by spectral methods and quantum-chemical calculations. The 2E3MPIn polymer showed good thermal stability compared to the starting PClPA polymer. A study of the photoluminescence of polymers showed that the emission spectrum of 2E3MPIn demonstrated a bathochromic shift (16 nm) and a considerable increase in the luminescence intensity in comparison to PClPA. The 2E3MPIn sample was found to possess photoconductivity. Irradiation of the polymer film increases the electrical conductivity by a factor of 2. The electrochemical properties obtained from the UV–vis spectrum and cyclic voltammograms suggest that 2E3MPIn has good electroactivity. A sample of 2E3MIn demonstrates a fine porous structure resembling a “sponge”. In addition, the PClPA and 2E3MPIn samples synthesized were used as sensitive materials in resistive moisture sensors. The 2E3MPIn polymer demonstrated a higher response than PClPA to changes in the environment humidity. The observed changes in the physicochemical properties of 2E3MPIn compared to PClPA confirm that the polyheterocyclization reaction occurs successfully and can be considered as an efficient way for synthesizing new functional polymers of the indole series.

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“…Electrolysis of indole and indole derivatives in non-aqueous solvents (LiClO 4 ÀCH 3 CN, CH 2 Cl) or in aqueous acid solution (HCl, HClO 4 ) can lead to polymerisation [15,[23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Pathways of Electrochemical Oxidation of Indolic Compounds

2011

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The electrochemical behaviour of indole and a group of indole-containing compounds with a substituent at the C3 position, indol-3-acetamide (IAM), tryptamine, gramine, indole acetic acid (IAA), indole propionic acid (IPA), indole butyric acid (IBA) and tryptophan, was investigated at a glassy carbon electrode, in order to determine their oxidation pathways. Indole undergoes one irreversible pH dependent oxidation, whereas the oxidation process of indole derivatives was more complex, a two step, the oxidation at C2 position on the pyrrole ring followed by the hydroxylation at the C7 position of the benzene moiety of indoles, irreversible pH dependent oxidation.

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Electrochemical polymerization and spectroscopic investigation of 2-methylindole

Cited by 20 publications

References 19 publications

Carbon and Nitrogen K-Edge NEXAFS Spectra of Indole, 2,3-Dihydro-7-azaindole, and 3-Formylindole

Carbon and Nitrogen K-Edge NEXAFS Spectra of Indole, 2,3-Dihydro-7-azaindole, and 3-Formylindole

Synthesis and Physicochemical Properties of Poly(2-ethyl-3-methylindole)

Pathways of Electrochemical Oxidation of Indolic Compounds

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