Special Section on Solution-Processable Organic Solar Cells

Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units

[+] Author Affiliations
Yuriy N. Luponosov, Dmitry A. Khanin, Georgiy V. Cherkaev, Evgeniya A. Svidchenko

Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences, Profsoyuznaya Street 70, Moscow 117393, Russia

Jie Min, Derya Baran, Tayebeh Ameri

Friedrich-Alexander University Erlangen-Nuremberg, Institute of Materials for Electronics and Energy Technology (I-MEET), Martensstraße 7, 91058 Erlangen, Germany

Sergey A. Pisarev

Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences, Profsoyuznaya Street 70, Moscow 117393, Russia

Russian Academy of Sciences, Institute of Physiologically Active Compounds, Severny Proezd 1, Chernogolovka 142432, Russia

Svetlana M. Peregudova

Russian Academy of Sciences, Nesmeyanov Institute of Organoelement Compounds, Vavilova Street 28, Moscow 119991, Russia

Petr V. Dmitryakov

Scientific and Research Centre Kurchatov Institute, 1 Kurchatov Square, Moscow 123182, Russia

Sergei N. Chvalun

Friedrich-Alexander University Erlangen-Nuremberg, Institute of Materials for Electronics and Energy Technology (I-MEET), Martensstraße 7, 91058 Erlangen, Germany

Scientific and Research Centre Kurchatov Institute, 1 Kurchatov Square, Moscow 123182, Russia

Christoph J. Brabec

Friedrich-Alexander University Erlangen-Nuremberg, Institute of Materials for Electronics and Energy Technology (I-MEET), Martensstraße 7, 91058 Erlangen, Germany

Bavarian Center for Applied Energy Research (ZAE Bayern), Haberstraße 2a, 91058 Erlangen, Germany

Sergei A. Ponomarenko

Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences, Profsoyuznaya Street 70, Moscow 117393, Russia

Moscow State University, Chemistry Department, Leninskie Gory 1-3, Moscow 119991, Russia

J. Photon. Energy. 5(1), 057213 (Feb 16, 2015). doi:10.1117/1.JPE.5.057213
History: Received October 7, 2014; Accepted January 7, 2015
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Abstract.  Two π-conjugated acceptor-donor-acceptor-donor-acceptor-type (A-D-A-D-A) oligothiophenes, TT-(2T-DCV-Hex)2 and BT-(2T-DCV-Hex)2 were designed and synthesized with thienothiadiazole (TT) or benzothiadiazole (BT) as the core and dicyanovinyl (DCV) as the terminal acceptor groups for comprehensively investigating and understanding structure–property relationships. The resulting oligomers were first characterized by thermal analysis, UV-Vis spectroscopy, and cyclic voltammetry. By simply changing the BT to TT core in these two oligothiophenes, the highest occupied molecular orbital levels were varied from 5.55eV for BT-(2T-DCV-Hex)2 to 5.11eV for TT-(2T-DCV-Hex)2, and the optical band gaps were varied from 1.72 eV for BT-(2T-DCV-Hex)2 to 1.25 eV for TT-(2T-DCV-Hex)2, ascribed to the stronger electron accepting character of the TT core. However, the power conversion efficiency of bulk heterojunction organic solar cells (OSCs) with TT-(2T-DCV-Hex)2 as donor and [6,6]-phenyl C70-butyric acid methyl ester (PC71BM) as acceptor was measured to be 0.04% only, which is much lower than that of BT-(2T-DCV-Hex)2:PC71BM (1.54%). Compared to the TT-(2T-DCV-Hex)2 system, the BT-(2T-DCV-Hex)2 based device shows smoother film surface morphology, and superior charge generation and charge carrier mobilities. Therefore, the results clearly demonstrate that in addition to modifying the alkyl side chains and π-bridge lengths, the design of new small molecules for high-performance OSCs should also aim to choose suitable acceptor units.

Figures in this Article
© 2015 Society of Photo-Optical Instrumentation Engineers

Citation

Yuriy N. Luponosov ; Jie Min ; Dmitry A. Khanin ; Derya Baran ; Sergey A. Pisarev, et al.
"Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units", J. Photon. Energy. 5(1), 057213 (Feb 16, 2015). ; http://dx.doi.org/10.1117/1.JPE.5.057213


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