Low band-gap polymeric photovoltaic devices

Shaheen, S.E.; Vangeneugden, Dirk; Kiebooms, R.; Vanderzande, Dirk; Fromherz, T.; Padinger, F.; Brabec, Christoph J.; Sariciftci, Niyazi Serdar

doi:10.1016/s0379-6779(00)01501-0

Cited by 82 publications

(106 citation statements)

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“…[5][6][7][8] Until now, EDOT-based oligomers have not received as much attention, probably because they are difficult to synthesize and, in case of the longer species, sensitive to air oxidation. Recently published studies on oligomers of EDOT include bis 2-͑3,4-ethylenedioxy͒thienyl that can be electrochemically polymerized to form electrochromic conducting polymers, 9 and ␣, -bis͑mesitylthio͒͑3,4-ethylenedioxythiophene͒ for molecular scale electronics applications.…”

Section: Introductionmentioning

confidence: 99%

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The electronic structure of n- and p-doped phenyl-capped 3,4-ethylenedioxythiophene trimer

Jong

Gon

Crispin

et al. 2003

The Journal of Chemical Physics

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Document VersionPublisher's PDF, also known as Version of Record (includes final page, issue and volume numbers)Please check the document version of this publication:• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. The phenyl-capped 3,4-ethylenedioxythiophene ͑EDOT͒ trimer is a well-defined oligomer of the related poly͑3,4-ethylenedioxythiophene͒, the conjugated polymer that forms the basis of the commercialized conducting polymer ''PEDOT-PSS.'' EDOT-based oligomers are themselves potential candidates for applications in molecular electronics, such as organic field effect transistors and organic solar cells. Well controlled chemical doping is of importance in such applications, since it enables tuning of important properties such as the electrical conductivity, the position of the Fermi-level, the optical absorption edge, and the quantum efficiency for photovoltaic devices. The effects of chemical doping, both p-type doping with iodine, and n-type doping with lithium, on the electronic structure of condensed molecular solid films of EDOT trimer have been studied using ultraviolet photoelectron spectroscopy and x-ray photoelectron spectroscopy. The results are discussed in terms of parameters important for device applications.

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Section: Introductionmentioning

confidence: 99%

“…This has recently been demonstrated for polythiophenes and oligothiophenes containing various electron-donating groups. 5,6 Additionally, EDOT oligomers have a more rigid planar -electron system compared to thiophene oligomers, 1 which is thought to be due to intrachain interactions between sulfur and oxygen atoms. 1,11,12 …”

Section: Introductionmentioning

confidence: 99%

The electronic structure of n- and p-doped phenyl-capped 3,4-ethylenedioxythiophene trimer

Jong

Gon

Crispin

et al. 2003

The Journal of Chemical Physics

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“…The substitution also causes the optical absorption spectrum to be red-shifted, which is promising for organic solar cell applications, for which the collection of the low-energy part of the solar spectrum is a major issue. 9,10 Phenyl-capped 3,4-ethylenedioxythiophene oligomers, Ph-͑EDOT) n -Ph, were recently synthesized 11 ͑see Fig. 1͒.…”

Section: Introductionmentioning

confidence: 99%

A joint theoretical and experimental study on the electronic properties of phenyl-capped 3,4-ethylenedioxythiophene oligomers

Osikowicz

Gon

Crispin

et al. 2003

The Journal of Chemical Physics

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Document VersionPublisher's PDF, also known as Version of Record (includes final page, issue and volume numbers)Please check the document version of this publication:• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication Citation for published version (APA):Osikowicz, W., Denier van der Gon, A. W., Crispin, X., Jong, de, M. P., Friedlein, R., Groenendaal, L., ... Salaneck, W. R. (2003). A joint theoretical and experimental study on the electronic properties of phenyl-capped 3,4-ethylenedioxythiophene oligomers. Journal of Chemical Physics, 119(19), 10415-10420. DOI: 10.1063/1.1617273 General rightsCopyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. The electronic structure of a series of phenyl-capped 3,4-ethylenedioxythiophene oligomers has been studied using ultraviolet photoelectron spectroscopy ͑UPS͒ in combination with theoretical calculations. The calculations were performed for isolated oligomers within the framework of density-functional theory, using the BeckeϩLee-Yang-Parr exchange-correlation functional. Excellent agreement between the UPS spectra and the quantum-chemical calculations allowed for unambiguous interpretation of the results. We use the asymptotic extension of electronic properties of oligomers to discuss the electronic structure of neutral poly͑3,4-ethylenedioxythiophene͒. In addition, experimentally determined ionization potentials for thin films prepared by vapor deposition and spin coating are reported, and are found to depend on the preparation method. The discrepancy is assigned to differences in the molecular packing.

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“…32À36 In recent work, the precursor route toward poly(3-octylthienylene vinylene) (O-PTV) has been explored extensively by NMR spectroscopy to identify and quantify the polymer end groups and possible structural defects due to, e.g., head-to-head or tail-to-tail monomer additions during the polymerization process. 37 For that purpose, 13 C-labeled vinylene carbons were introduced into the polymer chains. Solubility in several organic solvents was ensured by the long octyl side chains.…”

Section: ' Introductionmentioning

confidence: 99%

“…6.81 (dd, J 1 = 3.5, J 2 = 1.3, 1H), 5.62 (dd, J 1 = 9.9, J 2 = 4.7, 1H), 4.01 (q, J = 6.9, 2H), 3.84 (dd, J 1 = 14.8, J 2 = 4.7, 1H), 3.69 (q, J = 6.9, 2H), 3.43 (dd, J 1 = 14.8, J 2 = 9.9, 1H), 1.26 (t, J = 6.9, 3H), 1.25 (t, J = 6.9, 3H). 13 Step 1: 1-(Thiophen-2-yl)-2-(trimethylsilyl)ethanol. Chloromethyltrimethylsilane (6.1 g, 50.0 mmol) was added dropwise to a suspension of magnesium turnings (1.25 g, 50 mmol) in dry THF (150 mL), and the mixture was allowed to react under reflux conditions for 4 h. To the freshly prepared Grignard solution, cooled to À78°C, was added dropwise thiophene-2-carbaldehyde (5.32 g, 47.5 mmol).…”

Section: Introductionmentioning

confidence: 99%

Fingerprints for Structural Defects in Poly(thienylene vinylene) (PTV): A Joint Theoretical–Experimental NMR Study on Model Molecules

et al. 2011

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Low band-gap polymeric photovoltaic devices

Cited by 82 publications

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The electronic structure of n- and p-doped phenyl-capped 3,4-ethylenedioxythiophene trimer

The electronic structure of n- and p-doped phenyl-capped 3,4-ethylenedioxythiophene trimer

A joint theoretical and experimental study on the electronic properties of phenyl-capped 3,4-ethylenedioxythiophene oligomers

Fingerprints for Structural Defects in Poly(thienylene vinylene) (PTV): A Joint Theoretical–Experimental NMR Study on Model Molecules

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