Structural and electronic properties of 3,4-ethylenedioxythiophene, 3,4-ethylenedisulfanylfurane and thiophene oligomers: A theoretical investigation

Alemán, Carlos; Armelín, Elaine; Iribarren, José I.; Liesa, Francisco; Laso, Manuel; Casanovas, Jordi

doi:10.1016/j.synthmet.2004.12.012

Cited by 57 publications

(50 citation statements)

References 41 publications

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“…In theoretical studies of PEDOT and PEDOT:PSS in the literature [18,[20][21][22][23] oligomers have been used to investigate the geometrical packing of PEDOT and its counter ions, as well as their interactions. Combined HF/6-31-G*, MP2/6-31++G** 3 and forcefield calculations of a charged PEDOT octamer and a toluensulphonic acid counter ion showed that the perpendicular position of the counter ion to the PEDOT chain is the most stable of the studied positions [21].…”

Section: Introductionmentioning

confidence: 99%

The electronic structure and reflectivity of PEDOT:PSS from density functional theory

et al. 2011

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The geometric and electronic structure of condensed phase organic conducting polymer PEDOT:PSS blends has been investigated by periodic density functional theory (DFT) calculations with a generalized-gradient approximation (GGA) functional, and a plane wave basis set. The influence of the degree of doping of the PEDOT polymer on structural and optical parameters such as the reflectivity, absorbance, conductivity, dielectric function, refractive index and the energy-loss function is studied. A flip from the benzoid to the quinoid structure is observed in the calculations when the neutral PEDOT is doped by negatively charged PSS. Also the optical properties are affected by the doping. In particular, the reflectivity was found to be very sensitive to the degree of doping, where higher doping implies higher reflectivity. The reflectivity is highly anisotropic, with the dominant contribution stemming from the direction parallel to the PEDOT polymer chain.

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Section: Introductionmentioning

confidence: 99%

The electronic structure and reflectivity of PEDOT:PSS from density functional theory

et al. 2011

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“…The large variation in the reported results can be attributed to differences in choice of functional, finite size scaling method used (or absence thereof), and geometrical details. 4,17,34,35,41,42 In these earlier studies, larger gaps were found for shorter oligomers compared to longer oligomers 41 . Also, the generalized gradient correction was found to give small gaps 17 whereas the B3LYP functional was found to give larger gaps 41 in closer agreement with experiment.…”

Section: 253435mentioning

confidence: 75%

Temperature dependence of band gaps and conformational disorder in PEDOT and its selenium and tellurium derivatives: Density functional calculations

Mirsakiyeva

Hugosson

Linares

et al. 2017

The Journal of Chemical Physics

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PostprintThis is the accepted version of a paper published in Journal of Chemical Physics. This paper has been peer-reviewed but does not include the final publisher proof-corrections or journal pagination.Citation for the original published paper (version of record):Mirsakiyeva, A., Hugosson, H W., Linares, M., Delin, A. (2017) Temperature dependence of band gaps and conformational disorder in PEDOT and its selenium and tellurium derivatives: density functional calculations. Journal of Chemical PhysicsAccess to the published version may require subscription. N.B. When citing this work, cite the original published paper. Permanent link to this version:http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-214934Temperature dependence of band gaps and conformational disorder in PEDOT and its selenium and tellurium derivatives: density functional calculations The conducting polymer poly(3,4-ethylenedioxythiophene), or PEDOT, is an attractive material for flexible electronics. We present combined molecular dynamics and quantum chemical calculations, based on density functional theory, of EDOT oligomers and isoelectronic selenium and tellurium derivatives (EDOS and EDOTe) to address the effect of temperature on the geometrical and electronic properties of these systems.With finite size scaling, we also extrapolate our results to the infinite polymers, i.e. PEDOT, PEDOS and PEDOTe. Our computations indicate that the most favourable oligomer conformations at finite temperature are conformations around the flat trans-conformation and a non-flat conformation around 45• from the cis-conformation. Also, the dihedral stiffness increases with the atomic number of the heteroatom. We find excellent agreement with experimentally measured gaps for PEDOT and PEDOS. For PEDOT, the gap does not increase with temperature whereas this is the case for its derivatives. The conformational disorder as well as the choice of basis set both significantly affect the calculated gaps.

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“…In fact, the torsional angle constitutes a compromise between the effect of conjugation and the steric repulsion between hydrogen which favors a nonplanar structure. In comparison with the torsional angles obtained in the case of PEDOT [48,49] (θ i = 180.0 ± 5.0 • ) and in the case of n-THP (oligothiophenes) [50,51] (θ i ≈ 150.0 • ) where the anticonformation was predicted as the global minimum at different levels of theory, that is, HF, B3LYP, B3PW91, and MP2 combined with different basis sets, the effect of insertion of PVK motive is clearly seen. However, the introduction of charges carriers into carbazole enhances the π-conjugated structures.…”

Section: Geometric Parametersmentioning

confidence: 90%

Chemical Synthesis, Electronic Study, and Vibrational Analysis of a New Organic Copolymer Based on PVK and 3-nhexylthiophene

et al. 2010

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Conjugated polymers containing carbazole moieties either in the main or in the side chains have attracted much attention because of their unique electronic properties, to their high photoluminescence quantum efficiency, and thermal stability. The aim of this work is to study a new organic copolymer which combines the PVK properties and those of PHT. We will describe in this study the protocol synthesis, the chemical structure, and the electronic and vibrational properties of the resulting copolymer. The experimental and theoretical studies are combined in order to describe the properties of this material. These properties suggest this compound (PVK-PHT) to be a good candidate for optoelectronic application.

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Structural and electronic properties of 3,4-ethylenedioxythiophene, 3,4-ethylenedisulfanylfurane and thiophene oligomers: A theoretical investigation

Cited by 57 publications

References 41 publications

The electronic structure and reflectivity of PEDOT:PSS from density functional theory

The electronic structure and reflectivity of PEDOT:PSS from density functional theory

Temperature dependence of band gaps and conformational disorder in PEDOT and its selenium and tellurium derivatives: Density functional calculations

Chemical Synthesis, Electronic Study, and Vibrational Analysis of a New Organic Copolymer Based on PVK and 3-nhexylthiophene

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