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Title: Benzo[ b]selenophene/thieno[3,2- b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers
Authors: Demina, N. S.
Rasputin, N. A.
Irgashev, R. A.
Tameev, A. R.
Nekrasova, N. V.
Rusinov, G. L.
Nunzi, J. -M.
Charushin, V. N.
Issue Date: 2020
Publisher: American Chemical Society
Citation: Benzo[ b]selenophene/thieno[3,2- b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers / N. S. Demina, N. A. Rasputin, R. A. Irgashev, et al. — DOI 10.1021/acsomega.0c00383 // ACS Omega. — 2020. — Vol. 5. — Iss. 16. — P. 9377-9383.
Abstract: Two series of new N,S,Se-heteroacenes, namely, 6H-benzo[4′,5′]selenopheno[2′,3′:4,5]thieno[3,2-b]indoles and 12H-benzo[4″,5″]selenopheno[2″,3″:4′,5′]thieno[2′,3′4,5]thieno[3,2-b]indoles, were successfully obtained using an effective strategy based on Fiesselmann thiophene and Fischer indole synthesis. The new molecules exhibit a large optical band gap (2.82 eV < Egopt < 3.23 eV) and their highest occupied molecular orbital (HOMO) energy formed by the plane π-core ranges between -5.2 and -5.6 eV, with the narrower optical band gap and lower HOMO level corresponding to selenated heteroacenes. In thin solid films of the heteroacenes, hole mobility measured using the conventional CELIV technique ranges between 10-5 and 10-4 cm2·V-1·s-1. All these make the proposed condensed-ring compounds a promising platform for the development of hole-transporting materials applicable in organic electronics. Copyright © 2020 American Chemical Society.
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85084396891
PURE ID: 12932933
ISSN: 24701343
DOI: 10.1021/acsomega.0c00383
metadata.dc.description.sponsorship: The research (synthesis of new heteroacenes and investigation of their semiconductor properties) was financially supported by the Russian Science Foundation (project no. 18-13-00409). N.S.D. and N.A.R. would like to acknowledge the financial support for the analytical studies of synthesized compounds from the Ministry of Education and Science of the Russian Federation within the framework of the State Assignment for Research (project no. AAAA-A19-119012490006-1). The authors are grateful to Grigory A. Kim for carrying out the DFT calculations which were performed using ⟨⟨Uran⟩⟩ supercomputer of the Institute of Mathematic and Mechanics of the Ural Branch of the Russian Academy of Sciences. The XRD measurements were performed using the equipment of CKP FMI IPCE RAS.
RSCF project card: 18-13-00409
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