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Star-shaped conjugated molecules with oxa- or thiadiazole bithiophene side arms.

Kotwica, Kamil and Kostyuchenko, Anastasia S. and Data, Przemyslaw and Marszalek, Tomasz and Skorka, Lukasz and Jaroch, Tomasz and Kacka, Sylwia and Zagorska, Malgorzata and Nowakowski, Robert and Monkman, Andrew P. and Fisyuk, Alexander S. and Pisula, Wojciech and Pron, Adam (2016) 'Star-shaped conjugated molecules with oxa- or thiadiazole bithiophene side arms.', Chemistry : a European journal., 22 (33). pp. 11795-11806.

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.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1002/chem.201600984
Publisher statement:This is the peer reviewed version of the following article: K. Kotwica, A. S. Kostyuchenko, P. Data, T. Marszalek, L. Skorka, T. Jaroch, S. Kacka, M. Zagorska, R. Nowakowski, A. P. Monkman, A. S. Fisyuk, W. Pisula, A. Pron, Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms. Chemistry - A European Journal 2016, 22(33): 11795-11806, which has been published in final form at https://doi.org/10.1002/chem.201600984. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.
Date accepted:No date available
Date deposited:11 August 2017
Date of first online publication:12 July 2016
Date first made open access:11 August 2017

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