Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules

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Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules. / Baranov, Denis S.; Nevostruev, Danil A.; Kazantsev, Maxim S. et al.

In: ChemistrySelect, Vol. 6, No. 24, 28.06.2021, p. 6043-6049.

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

BibTeX

@article{beba40556bd544d3a315330c84dcb314,

title = "Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules",

abstract = "Two acceptor small molecules consisting of 2-(11-oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile frameworks connected by a bis(thiophen-2-ylethynyl)arene bridge were synthesized by the two-step sequence of Sonogashira cross-coupling and Knoevenagel condensation in order to investigate their performance as non-fullerene acceptors in organic solar cells. Optical, electrochemical and photovoltaic properties of new 2,2′-[2,2′-(5,5′-(arenediyl)bis(ethyne-2,1-diyl)bis(thien-5,2-diyl))bis(11-oxoanthra[2,1-b]thiophen-6-ylidene)]dipropanedinitriles and previously studied analogs of 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were compared to assess the effect of introducing ethynylthiophene units between the arene linker and the 2-(11-oxoanthrathiophen-6-ylidene)propanedinitrile units. Despite the proper energy level alignment and morphology, composites of the newly synthesized compounds with the PBDB-T donor polymer demonstrate a moderate PCE of 0.54 %. The small value of the short circuit current as compared to composites with fullerene acceptors is probably due to the low electron mobility in the newly synthesized compounds. The low electron mobility, in turn, is probably cause by the LUMO localization at the edge units of the acceptor-type molecules, in contrast to the almost uniform LUMO delocalization over the whole π-conjugated system for high-performing non-fullerene acceptors such as ITIC.",

keywords = "Electron-deficient compounds, Fused-ring systems, Polycycles, Solar Cells, Sulfur heterocycles",

author = "Baranov, {Denis S.} and Nevostruev, {Danil A.} and Kazantsev, {Maxim S.} and Zinoviev, {Vladimir A.} and Zelentsova, {Ekaterina A.} and Dmitriev, {Alexey A.} and Gritsan, {Nina P.} and Tsentalovich, {Yuri P.} and Maria Kotova and Johannes D{\"u}reth and Andreas Sperlich and Vladimir Dyakonov and Kulik, {Leonid V.}",

note = "Funding Information: The reported study was funded by RFBR, projects number 19-03-00149 and number 20-33-70126. Maria Kotova, Andreas Sperlich and Vladimir Dyakonov acknowledge EU H2020-MSCA-ITN-2016 ?SEPOMO? 722651. Funding Information: . The reported study was funded by RFBR, projects number 19‐03‐00149 and number 20‐33‐70126. Maria Kotova, Andreas Sperlich and Vladimir Dyakonov acknowledge EU H2020‐MSCA‐ITN‐2016 “SEPOMO” 722651 Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = jun,

day = "28",

doi = "10.1002/slct.202101491",

language = "English",

volume = "6",

pages = "6043--6049",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "24",

}

RIS

TY - JOUR

T1 - Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules

AU - Baranov, Denis S.

AU - Nevostruev, Danil A.

AU - Kazantsev, Maxim S.

AU - Zinoviev, Vladimir A.

AU - Zelentsova, Ekaterina A.

AU - Dmitriev, Alexey A.

AU - Gritsan, Nina P.

AU - Tsentalovich, Yuri P.

AU - Kotova, Maria

AU - Düreth, Johannes

AU - Sperlich, Andreas

AU - Dyakonov, Vladimir

AU - Kulik, Leonid V.

N1 - Funding Information: The reported study was funded by RFBR, projects number 19-03-00149 and number 20-33-70126. Maria Kotova, Andreas Sperlich and Vladimir Dyakonov acknowledge EU H2020-MSCA-ITN-2016 ?SEPOMO? 722651. Funding Information: . The reported study was funded by RFBR, projects number 19‐03‐00149 and number 20‐33‐70126. Maria Kotova, Andreas Sperlich and Vladimir Dyakonov acknowledge EU H2020‐MSCA‐ITN‐2016 “SEPOMO” 722651 Publisher Copyright: © 2021 Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/6/28

Y1 - 2021/6/28

N2 - Two acceptor small molecules consisting of 2-(11-oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile frameworks connected by a bis(thiophen-2-ylethynyl)arene bridge were synthesized by the two-step sequence of Sonogashira cross-coupling and Knoevenagel condensation in order to investigate their performance as non-fullerene acceptors in organic solar cells. Optical, electrochemical and photovoltaic properties of new 2,2′-[2,2′-(5,5′-(arenediyl)bis(ethyne-2,1-diyl)bis(thien-5,2-diyl))bis(11-oxoanthra[2,1-b]thiophen-6-ylidene)]dipropanedinitriles and previously studied analogs of 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were compared to assess the effect of introducing ethynylthiophene units between the arene linker and the 2-(11-oxoanthrathiophen-6-ylidene)propanedinitrile units. Despite the proper energy level alignment and morphology, composites of the newly synthesized compounds with the PBDB-T donor polymer demonstrate a moderate PCE of 0.54 %. The small value of the short circuit current as compared to composites with fullerene acceptors is probably due to the low electron mobility in the newly synthesized compounds. The low electron mobility, in turn, is probably cause by the LUMO localization at the edge units of the acceptor-type molecules, in contrast to the almost uniform LUMO delocalization over the whole π-conjugated system for high-performing non-fullerene acceptors such as ITIC.

AB - Two acceptor small molecules consisting of 2-(11-oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile frameworks connected by a bis(thiophen-2-ylethynyl)arene bridge were synthesized by the two-step sequence of Sonogashira cross-coupling and Knoevenagel condensation in order to investigate their performance as non-fullerene acceptors in organic solar cells. Optical, electrochemical and photovoltaic properties of new 2,2′-[2,2′-(5,5′-(arenediyl)bis(ethyne-2,1-diyl)bis(thien-5,2-diyl))bis(11-oxoanthra[2,1-b]thiophen-6-ylidene)]dipropanedinitriles and previously studied analogs of 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were compared to assess the effect of introducing ethynylthiophene units between the arene linker and the 2-(11-oxoanthrathiophen-6-ylidene)propanedinitrile units. Despite the proper energy level alignment and morphology, composites of the newly synthesized compounds with the PBDB-T donor polymer demonstrate a moderate PCE of 0.54 %. The small value of the short circuit current as compared to composites with fullerene acceptors is probably due to the low electron mobility in the newly synthesized compounds. The low electron mobility, in turn, is probably cause by the LUMO localization at the edge units of the acceptor-type molecules, in contrast to the almost uniform LUMO delocalization over the whole π-conjugated system for high-performing non-fullerene acceptors such as ITIC.

KW - Electron-deficient compounds

KW - Fused-ring systems

KW - Polycycles

KW - Solar Cells

KW - Sulfur heterocycles

UR - http://www.scopus.com/inward/record.url?scp=85110522112&partnerID=8YFLogxK

U2 - 10.1002/slct.202101491

DO - 10.1002/slct.202101491

M3 - Article

AN - SCOPUS:85110522112

VL - 6

SP - 6043

EP - 6049

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 24

ER -

ID: 29238478