Year

2016

Type(s)

Journal Article

Author(s)

Kotwica, K. and Kostyuchenko, A.S. and Data, P. and Marszalek, T. and Skorka, L. and Jaroch, T. and Kacka, S. and Zagorska, M. and Nowakowski, R. and Monkman, A.P. and Fisyuk, A.S. and Pisula, W. and Pron, A.

Source

Chemistry - A European Journal, 22(33): 11795—11806, 2016

Url

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84979902021&doi=10.1002%2fchem.201600984&partnerID=40&md5=ba810b83cd3c07e74c27c0789a0bb0b2

BibTeX

BibTeX

BibTeX

@ARTICLE{Kotwica201611795, author={Kotwica, K. and Kostyuchenko, A.S. and Data, P. and Marszalek, T. and Skorka, L. and Jaroch, T. and Kacka, S. and Zagorska, M. and Nowakowski, R. and Monkman, A.P. and Fisyuk, A.S. and Pisula, W. and Pron, A.}, title={Star-Shaped Conjugated Molecules with Oxa- or Thiadiazole Bithiophene Side Arms}, journal={Chemistry - A European Journal}, year={2016}, volume={22}, number={33}, pages={11795-11806}, doi={10.1002/chem.201600984}, note={cited By 15}, url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-84979902021&doi=10.1002%2fchem.201600984&partnerID=40&md5=ba810b83cd3c07e74c27c0789a0bb0b2}, affiliation={Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, 00664, Poland; Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira av. 55A, Omsk, Russian Federation; Laboratory of New Organic Materials, Omsk State Technical University, Mira av. 11, Omsk, 644050, Russian Federation; Physics Department, University of Durham, South Road, Durham, DH1 3LE, United Kingdom; Max Planck Institute for Polymer Research, Ackermannweg 10, Mainz, 55128, Germany; Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw, 01224, Poland; Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, Lodz, 90-924, Poland}, 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}, author_keywords={electron transport; host–guest systems; self-assembly; semiconductors; supramolecular chemistry}, keywords={Electrochromism; Electron transport properties; Energy gap; Light emitting diodes; Molecules; Organic compounds; Scanning tunneling microscopy; Semiconductor materials; Spectroelectrochemistry; Stars; Supramolecular chemistry; Synthesis (chemical); X ray scattering, Conjugated molecules; Electrochromic behavior; Electroluminophores; Electron transport; Oxadiazole derivatives; Spectroelectrochemical study; Structural studies; Trifunctional monomers, Self assembly}, funding_details={Russian Foundation for Basic ResearchRussian Foundation for Basic Research, RFBR, 16-33-00340 mol_a, 15-43-04313-Sibiria-a}, funding_details={2015/17/B/ST5/00179}, funding_details={European Social FundEuropean Social Fund, ESF, 283}, funding_details={European CommissionEuropean Commission, EC}, funding_text 1={K.K., L.S., S.K., M.Z., and A.P. wish to acknowledge financial support from National Centre of Science in Poland (NCN, Grant No. 2015/17/B/ST5/00179). A.S.F. and A.S.K. acknowledge partial financial support from the Russian Foundation for Basic Research (15-43-04313-Sibiria-a) and (16-33-00340 mol_a). This work has been also supported by the European Union in the framework of European Social Fund through the Warsaw University of Technology Development Programme, realized by Center for Advanced Studies, granted for K. K. The Gaussian 09 calculations were carried out at the Wroclaw Centre for Networking and Supercomputing (WCSS) Wroclaw, Poland. http://www.wcss.wroc.pl, under computational Grant No. 283.}, references={Cherioux, F., Guyard, L., Audebert, P., (1998) Chem. Commun., pp. 2225-2226; Pron, A., Gawrys, P., Zagorska, M., Djurado, D., Demadrillea, R., (2010) Chem. Soc. Rev., 39, pp. 2577-2632; Ponomarenko, S.A., Kirchmeyer, S., Elschner, A., Huisman, B.H., Karbach, A., Drechsler, D., (2003) Adv. Funct. Mater., 13, pp. 591-596; Kim, K.H., Chi, Z., Cho, M.J., Jin, J., Cho, M.Y., Kim, S.J., Joo, J., Choi, D.H., (2007) Chem. 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Dostoevsky State University, Mira av. 55A, Russian Federation; email: fisyuk@chemomsu.ru}, publisher={Wiley-VCH Verlag}, issn={09476539}, coden={CEUJE}, language={English}, abbrev_source_title={Chem. Eur. J.}, document_type={Article}, source={Scopus},