Electrochemical and spectroelectrochemical investigations of small-bandgap π-conjugated polymers and their precursors

Schlick, Uwe; Teichert, Frank; Hanack, Michael

doi:10.1016/s0379-6779(98)80026-x

Cited by 58 publications

(9 citation statements)

References 42 publications

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“…However, upon subsequent CV scans, we observed two oxidation peaks in the CV between 0 V and 1 V that we attributed to a highly coloured, oligomeric species observed with related bis-(thienylvinyl)thiophenes formed during the reductive cycle. [59,65] On the first anodic scan of a clean electrode, the oxidation peaks between 0 and 1 V were absent, and after several cycles, we did not observe any visible film on the electrode surface owing to the solubility of the oligomeric species in THF.…”

Section: Resultsmentioning

confidence: 75%

“…The conversion to the bis(2-thienylacrylonitrile)-thiophene was nearly quantitative with yields ranging from 91-97 % in a 30 min reaction. Both Roncali et al [64] and Hanack et al [65] have synthesized the 3,4-proton version of 4a, which showed a λ max value at 480 nm in CH 2 Cl 2 and reversible oxidation and reduction waves. In addition, electrochemical anodic polymerization of the protonated derivative produced a polymer film with a band-gap of 0.65 eV.…”

Section: Resultsmentioning

confidence: 99%

“…The ab-sorption onsets of 5a-c were 600, 600 and 650 nm, respectively. For comparison, quinoidal thiophenes synthesized by Hanack et al [65,[68][69][70][71] bearing bis(2-thienyl)thiophene with 3,4-annulated phenyl and thiophene groups showed absorbance maxima at 432 and 405 nm, respectively. Additionally, non-annulated, quinoidal, terthiophenes showed an absorbance maximum at 554 nm.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Optical and Electronic Properties of Thiophene Derivatives

et al. 2009

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Using the Hinsberg synthesis of thiophenes, a versatile method to prepare fully derivatized, π-extended thiophenes is reported. Functionalized thiophenes were divergently synthesized to create three classes of compounds -electron-deficient, extended conjugation and electron-rich -to assess substituent effects on optical and electrochemical properties. Properties were assessed by solution absorption spectroscopy, solution-and solid-state fluorescence spectroscopy, cyclic voltammetry and density functional theory calculations. Tetracyano derivatives, prepared through Knoevenagel condensations of malononitrile with thiophene-2,5-dicarbaldehydes, were used as electron-poor analogs. These derivatives showed quasireversible reduction reactions and very low-lying calculated LUMO energies (-0.55 V reduction potentials vs. Fc/Fc + ). The effect of extending π conjugation

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Optical and Electronic Properties of Thiophene Derivatives

et al. 2009

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“…These chemicals, which have an extended π -conjugated structure, offer many advantages in terms of processability, and they show exceptional electrical conductivity properties. [2,5,9,[11][12][13][14][15] A significant portion of recent literature on plasma modification/deposition of substrates has focused on better controllability of film chemistry during depositions, with the goal of producing surface-active coatings. [16][17][18] Exant literature has explained clearly that pulsed plasma interactions on substrate surfaces, in general, result in higher retention of the monomer structure compared to continuous wave (CW) plasma polymerization.…”

Section: Introductionmentioning

confidence: 99%

Thiophene Deposition on Paper Surface by Pulsed RF-Plasma

Şahin

2015

Journal of Wood Chemistry and Technology

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Journal of Wood Chemistry and TechnologyPublication details, including instructions for authors and subscription information:The plasma duty cycle, in addition to power and exposure time, affects the surface atomic composition of thiophene plasma-treated paper. The elemental carbon and sulfur concentration increased from 56.7% to 78.6% and 0% to 13.4%, respectively, while oxygen decreased from 43.3% to 8.0% with the plasma treatment. Relatively large variations in the deposited film-like layer composition could be realized by changing plasma external parameters. The high-resolution (HR) C1s spectra of the thiophene plasma-treated paper clearly exhibit plasmainduced rearrangements and new sulfur functionalities on the paper surface. After a five-hour ex situ doping of thiophene plasma-treated papers with iodine, conductivity ranging from δ = 4.2E-2 to 4.1 S/cm was obtained. The low relative F/C atomic ratio after TFAA derivatization indicates that no hydroxyl groups were present on the paper surface after the thiophene plasma treatment.

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“…The π-conjugated systems along the main chain have been reported to be an effective electrically conductive layer [10]. However, it is not easy to prepare specific polymers such as heterocyclic polymers due to sensitive chemical groups.…”

Section: Introductionmentioning

confidence: 99%

Pyrrole thin films deposited on paper by pulsed RF plasma

Şahin

2007

Open Chemistry

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Attempts were made to plasma deposit an oriented π-conjugated polymer of pyrrole (Py) on paper surfaces in order to produce electrically conductive layers. The N/C atomic ratio of 0.13 − 0.24 was observed for all treatment conditions. This implies the nature of the deposition formed on the paper surface via pulsed plasma is different from that of pyrrole monomer. An increase in conductivity of all pyrrole-plasma treated papers was observed. The 50 W RF-power with 5 min plasma exposed paper sample shows 8.15 × 10 −9 S·cm −1 conductivity. The conductivity measurements indicated a plasmaenhanced ring-opening reaction mechanism of pyrrole.

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Electrochemical and spectroelectrochemical investigations of small-bandgap π-conjugated polymers and their precursors

Cited by 58 publications

References 42 publications

Synthesis and Optical and Electronic Properties of Thiophene Derivatives

Synthesis and Optical and Electronic Properties of Thiophene Derivatives

Thiophene Deposition on Paper Surface by Pulsed RF-Plasma

Pyrrole thin films deposited on paper by pulsed RF plasma

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