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

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

doi:10.1117/1.JPE.5.057213

16 February 2015 Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units

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

Author Affiliations +

Journal of Photonics for Energy, Vol. 5, Issue 1, 057213 (February 2015). https://doi.org/10.1117/1.JPE.5.057213

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.

Citation Download Citation

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, and Sergey A. Ponomarenko "Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units," Journal of Photonics for Energy 5(1), 057213 (16 February 2015). https://doi.org/10.1117/1.JPE.5.057213

Published: 16 February 2015

ACCESS THE FULL ARTICLE

INSTITUTIONAL
Select your institution to access the SPIE Digital Library.

SELECT YOUR INSTITUTION

PERSONAL
Sign in with your SPIE account to access your personal subscriptions or to use specific features such as save to my library, sign up for alerts, save searches, etc.

PERSONAL SIGN IN

No SPIE Account? Create one

PURCHASE THIS CONTENT

SUBSCRIBE TO DIGITAL LIBRARY

50 downloads per 1-year subscription

Members: $195

Non-members: $335 ADD TO CART

25 downloads per 1 - year subscription

Members: $145

Non-members: $250 ADD TO CART

PURCHASE SINGLE ARTICLE

Includes PDF, HTML & Video, when available