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Dicyanovinyl–Substituted Oligothiophenes: Structure-Property Relationships and Application in Vacuum-Processed Small Molecule Organic Solar Cells

  1. Roland Fitzner1,
  2. Egon Reinold1,
  3. Amaresh Mishra1,
  4. Elena Mena-Osteritz1,
  5. Hannah Ziehlke2,
  6. Christian Körner2,
  7. Karl Leo2,
  8. Moritz Riede2,
  9. Matthias Weil4,
  10. Olga Tsaryova3,
  11. André Weiß3,
  12. Christian Uhrich3,
  13. Martin Pfeiffer3,
  14. Peter Bäuerle1,*

Article first published online: 27 JAN 2011

DOI: 10.1002/adfm.201001639

Issue

Advanced Functional Materials

Advanced Functional Materials

Volume 21, Issue 5, pages 897–910, March 8, 2011

Additional Information

How to Cite

Fitzner, R., Reinold, E., Mishra, A., Mena-Osteritz, E., Ziehlke, H., Körner, C., Leo, K., Riede, M., Weil, M., Tsaryova, O., Weiß, A., Uhrich, C., Pfeiffer, M. and Bäuerle, P. (2011), Dicyanovinyl–Substituted Oligothiophenes: Structure-Property Relationships and Application in Vacuum-Processed Small Molecule Organic Solar Cells. Adv. Funct. Mater., 21: 897–910. doi: 10.1002/adfm.201001639

Author Information

  1. 1

    Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany

  2. 2

    Institute of Applied Photophysics, TU Dresden, Mommsenstraße 13, 01062 Dresden, Germany

  3. 3

    heliatek GmbH, Treidlerstr. 3, 01139 Dresden, Germany

  4. 4

    Institut für Chemische Technologien und Analytik, Abteilung Strukturchemie, Technische Universität Wien, Getreidemarkt 9/164-SC, 1060 Vienna, Austria

*Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany.

Publication History

  1. Issue published online: 25 FEB 2011
  2. Article first published online: 27 JAN 2011
  3. Manuscript Received: 6 AUG 2010

Funded by

  • German Research Foundation DFG
  • Ministry for Education and Research BMBF. Grant Number: OPEG 2010

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Keywords:

  • oligothiophenes;
  • dicyanovinylene acceptors;
  • bulk-heterojunction solar cells;
  • molecular packing;
  • structure–property relationships

Abstract

Efficient synthesis of a series of terminally dicyanovinyl (DCV)-substituted oligothiophenes, DCVnT 1–6, without solubilizing side chains synthesized via a novel convergent approach and their application as electron donors in vacuum-processed m-i-p-type planar and p-i-n-type bulk heterojunction organic solar cells is described. Purification of the products via gradient sublimation yields thermally highly stable organic semiconducting materials in single crystalline quality which allows for X-ray structure analysis. Important insights into the packing features and intermolecular interactions of these promising solar cell materials are provided. Optical absorption spectra and electrochemical properties of the oligomers are investigated and valuable structure–property relationships deduced. Photovoltaic devices incorporating DCVnTs 4–6 showed power conversion efficiencies up to 2.8% for planar and 5.2% for bulk heterojunction organic solar cells under full sun illumination (mismatch corrected simulated AM 1.5G sunlight). The 5.2% efficiency shown here represents one of the highest values ever reported for organic vacuum-deposited single heterojunction solar cells.

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