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Kotwica K, Kostyuchenko AS, Data P, et al. Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry. 2016;22(33):11795-806doi: 10.1002/chem.201600984.
Kotwica, K., Kostyuchenko, A. S., Data, P., Marszalek, T., Skorka, L., Jaroch, T., Kacka, S., Zagorska, M., Nowakowski, R., Monkman, A. P., Fisyuk, A. S., Pisula, W., & Pron, A. (2016). Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry (Weinheim an der Bergstrasse, Germany), 22(33), 11795-806. https://doi.org/10.1002/chem.201600984
Kotwica, Kamil, et al. "Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,33 (2016): 11795-806. doi: https://doi.org/10.1002/chem.201600984
Kotwica K, Kostyuchenko AS, Data P, Marszalek T, Skorka L, Jaroch T, Kacka S, Zagorska M, Nowakowski R, Monkman AP, Fisyuk AS, Pisula W, Pron A. Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry. 2016 Aug 08;22(33):11795-806. doi: 10.1002/chem.201600984. Epub 2016 Jul 12. PMID: 27404332.
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Chemistry. 2016 Aug 08;22(33):11795-806. doi: 10.1002/chem.201600984. Epub 2016 Jul 12.

Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kamil Kotwica, Anastasia S Kostyuchenko, Przemyslaw Data, Tomasz Marszalek, Lukasz Skorka, Tomasz Jaroch, Sylwia Kacka, Malgorzata Zagorska, Robert Nowakowski, Andrew P Monkman, Alexander S Fisyuk, Wojciech Pisula, Adam Pron

Affiliations

  1. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00664, Warsaw, Poland.
  2. Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira av. 55A, Omsk, Russian Federation.
  3. Laboratory of New Organic Materials, Omsk State Technical University, Mira av. 11, Omsk, 644050, Russian Federation.
  4. Physics Department, University of Durham, South Road, Durham, DH1 3LE, United Kingdom.
  5. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
  6. Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01224, Warsaw, Poland.
  7. Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira av. 55A, Omsk, Russian Federation. [email protected].
  8. Laboratory of New Organic Materials, Omsk State Technical University, Mira av. 11, Omsk, 644050, Russian Federation. [email protected].
  9. Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany. [email protected].
  10. Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924, Lodz, Poland. [email protected].
  11. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00664, Warsaw, Poland. [email protected].

PMID: 27404332 DOI: 10.1002/chem.201600984

Abstract

Star-shaped conjugated molecules, consisting of a benzene central unit symmetrically trisubstituted with either oxa- or thiadiazole bithiophene groups, were synthesized as promising molecules and building blocks for application in (opto)electronics and electrochromic devices. Their optical (Eg (opt)) as well as electrochemical (Eg (electro)) band gaps depended on the type of the side arm and the number of solubilizing alkyl substituents. Oxadiazole derivatives showed Eg (opt) slightly below 3 eV and by 0.2 eV larger than those determined for thiadiazole-based compounds. The presence of alkyl substituents in the arms additionally lowered the band gap. The obtained compounds were efficient electroluminophores in guest/host-type light-emitting diodes. They also showed a strong tendency to self-organize in monolayers deposited on graphite, as evidenced by scanning tunneling microscopy. The structural studies by X-ray scattering revealed the formation of supramolecular columnar stacks in which the molecules were organized. Differences in macroscopic alignment in the specimen indicated variations in the self-assembly mechanism between the molecules. The compounds as trifunctional monomers were electrochemically polymerized to yield the corresponding polymer network. As shown by UV/Vis-NIR spectroelectrochemical studies, these networks exhibited reversible electrochromic behavior both in the oxidation and in the reduction modes.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: electron transport; host-guest systems; self-assembly; semiconductors; supramolecular chemistry

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