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Journal of Photonics for Energy

Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units
Author(s): Yuriy N. Luponosov; Jie Min; Dmitry A. Khanin; Derya Baran; Sergey A. Pisarev; Svetlana M. Peregudova; Petr V. Dmitryakov; Sergei N. Chvalun; Georgiy V. Cherkaev; Evgeniya A. Svidchenko; Tayebeh Ameri; Christoph J. Brabec; Sergey A. Ponomarenko
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Paper 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 −5.55  eV for BT-(2T-DCV-Hex)2 to −5.11  eV 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.

Paper Details

Date Published: 16 February 2015
PDF: 17 pages
J. Photon. Energy. 5(1) 057213 doi: 10.1117/1.JPE.5.057213
Published in: Journal of Photonics for Energy Volume 5, Issue 1
Show Author Affiliations
Yuriy N. Luponosov, Institute of Synthetic Polymeric Materials (Russia)
Jie Min, Friedrich-Alexander-Univ. Erlangen-Nürnberg (Germany)
Dmitry A. Khanin, Institute of Synthetic Polymeric Materials (Russian Federation)
Derya Baran, Friedrich-Alexander-Univ. Erlangen-Nürnberg (Germany)
Sergey A. Pisarev, Institute of Synthetic Polymeric Materials (Russia)
Svetlana M. Peregudova, A.N. Nesmeyanov Institute of Organoelement Compounds (Russian Federation)
Petr V. Dmitryakov, Russian Research Ctr. Kurchatov Institute (Russian Federation)
Sergei N. Chvalun, Friedrich-Alexander-Univ. Erlangen-Nürnberg (Germany)
Russian Research Ctr. Kurchatov Institute (Russia)
Georgiy V. Cherkaev, Institute of Synthetic Polymeric Materials (Russia)
Evgeniya A. Svidchenko, Institute of Synthetic Polymeric Materials (Russia)
Tayebeh Ameri, Friedrich-Alexander-Univ. Erlangen-Nürnberg (Germany)
Christoph J. Brabec, Friedrich-Alexander-Univ. Erlangen-Nürnberg (Germany)
Bavarian Center for Applied Energy Research (ZAE Bayern) (Germany)
Sergey A. Ponomarenko, Institute of Synthetic Polymeric Materials (Russia)
Moscow State University (Russia)


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