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; Sergei A. Ponomarenko

doi:10.1117/1.JPE.5.057213

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, Sergei A. Ponomarenko

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

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 p-bridge lengths, the design of new small molecules for high-performance OSCs should also aim to choose suitable acceptor units.

Original language	English (US)
Journal	Journal of Photonics for Energy
Volume	5
Issue number	1
DOIs	https://doi.org/10.1117/1.JPE.5.057213
State	Published - Jan 1 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 Society of Photo-Optical Instrumentation Engineers.

Keywords

Donor-acceptor oligomer
benzothiadiazole
charge carrier mobility
charge generation
dicyanovinyl group
organic solar cell
thienothiadiazole

ASJC Scopus subject areas

Atomic and Molecular Physics, and Optics
Renewable Energy, Sustainability and the Environment

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1117/1.JPE.5.057213

Cite this

Luponosov, Y. N., Min, J., Khanin, D. A., Baran, D., Pisarev, S. A., Peregudova, S. M., Dmitryakov, P. V., Chvalun, S. N., Cherkaev, G. V., Svidchenko, E. A., Ameri, T., Brabec, C. J., & Ponomarenko, S. A. (2015). 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). https://doi.org/10.1117/1.JPE.5.057213

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

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 p-bridge lengths, the design of new small molecules for high-performance OSCs should also aim to choose suitable acceptor units.",

keywords = "Donor-acceptor oligomer, benzothiadiazole, charge carrier mobility, charge generation, dicyanovinyl group, organic solar cell, thienothiadiazole",

author = "Luponosov, {Yuriy N.} and Jie Min and Khanin, {Dmitry A.} and Derya Baran and Pisarev, {Sergey A.} and Peregudova, {Svetlana M.} and Dmitryakov, {Petr V.} and Chvalun, {Sergei N.} and Cherkaev, {Georgiy V.} and Svidchenko, {Evgeniya A.} and Tayebeh Ameri and Brabec, {Christoph J.} and Ponomarenko, {Sergei A.}",

note = "Publisher Copyright: {\textcopyright} 2015 Society of Photo-Optical Instrumentation Engineers.",

year = "2015",

month = jan,

day = "1",

doi = "10.1117/1.JPE.5.057213",

language = "English (US)",

volume = "5",

journal = "Journal of Photonics for Energy",

issn = "1947-7988",

publisher = "SPIE",

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Luponosov, YN, Min, J, Khanin, DA, Baran, D, Pisarev, SA, Peregudova, SM, Dmitryakov, PV, Chvalun, SN, Cherkaev, GV, Svidchenko, EA, Ameri, T, Brabec, CJ & Ponomarenko, SA 2015, '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, vol. 5, no. 1. https://doi.org/10.1117/1.JPE.5.057213

TY - JOUR

T1 - Synthesis and photovoltaic effect in red/near-infrared absorbing A-D-A-D-A-type oligothiophenes containing benzothiadiazole and thienothiadiazole central units

AU - Luponosov, Yuriy N.

AU - Min, Jie

AU - Khanin, Dmitry A.

AU - Baran, Derya

AU - Pisarev, Sergey A.

AU - Peregudova, Svetlana M.

AU - Dmitryakov, Petr V.

AU - Chvalun, Sergei N.

AU - Cherkaev, Georgiy V.

AU - Svidchenko, Evgeniya A.

AU - Ameri, Tayebeh

AU - Brabec, Christoph J.

AU - Ponomarenko, Sergei A.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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 p-bridge lengths, the design of new small molecules for high-performance OSCs should also aim to choose suitable acceptor units.

AB - 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 p-bridge lengths, the design of new small molecules for high-performance OSCs should also aim to choose suitable acceptor units.

KW - Donor-acceptor oligomer

KW - benzothiadiazole

KW - charge carrier mobility

KW - charge generation

KW - dicyanovinyl group

KW - organic solar cell

KW - thienothiadiazole

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U2 - 10.1117/1.JPE.5.057213

DO - 10.1117/1.JPE.5.057213

M3 - Article

AN - SCOPUS:84923171882

SN - 1947-7988

VL - 5

JO - Journal of Photonics for Energy

JF - Journal of Photonics for Energy

IS - 1

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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