Benzo[ b]selenophene/thieno[3,2- b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers

Nadezhda S Demina; Nikolay A Rasputin; Roman A Irgashev; Alexey R Tameev; Natalia V Nekrasova; Gennady L Rusinov; Jean-Michel Nunzi; Valery N Charushin

doi:10.1021/acsomega.0c00383

Benzo[ b]selenophene/thieno[3,2- b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers

ACS Omega. 2020 Apr 17;5(16):9377-9383. doi: 10.1021/acsomega.0c00383. eCollection 2020 Apr 28.

Authors

Nadezhda S Demina^{1

2}, Nikolay A Rasputin^{1

2}, Roman A Irgashev^{1

2}, Alexey R Tameev^{1

3}, Natalia V Nekrasova³, Gennady L Rusinov^{1

2}, Jean-Michel Nunzi⁴, Valery N Charushin^{1

2}

Affiliations

¹ I. A. Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620990, Russia.
² Ural Federal University Named after the First President of Russia B.N. Yeltsin, Mira Str., 19, Ekaterinburg 620002, Russia.
³ A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Prosp., 31, Bld.4, Moscow 119071, Russia.
⁴ Department of Physics, Engineering Physics and Astronomy, Department of Chemistry, Queens University, 90 Bader Lane, Kingston, Ontario K7L-3N6, Canada.

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 < E _g ^opt < 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.