Synthesis of 2,2′-[2,2′-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)]tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics

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Synthesis of 2,2′-[2,2′-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)]tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics. / Baranov, Denis S.; Krivenko, Olga L.; Kazantsev, Maxim S. et al.

In: Synthetic Metals, Vol. 255, 116097, 01.09.2019.

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

BibTeX

@article{1c9643ef41fd42a193e39e61b06cacac,

title = "Synthesis of 2,2′-[2,2′-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)]tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics",

abstract = "Three novel molecules based on thiophene-fused 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) units linked through functionalized π-conjugated arene bridges are synthesized by three-step sequence of Sonagashira coupling, double thioannulation and Knoevenagel condensation. The energy of their frontier orbitals shows that these molecules are suitable for replacing fullerenes as electron acceptors in composites with conjugated donor polymers used in organic photovoltaics (OPV). The composite of polymer donor PCDTBT with fluorene-linked thiophene-fused TCAQs demonstrates good solubility in organic solvents and bulk heterojunction morphology with characteristic donor and acceptor domain size of several tens of nanometers, favourable for photoelectric conversion. This composite also exhibits prominent light-induced EPR signal indicating efficient photoinduced free charge generation. OPV devices based on this composite were fabricated by vacuum-free method. They show photoelectric conversion with maximum PCE of 0.71%.",

keywords = "Functionalized anthra[2,3-b]thiophenes, Non-fullerene acceptors, Photovoltaic properties, Synthesis, π-Extended TCNQ-based molecules, DESIGN, ACENES, SEMICONDUCTORS, 11,11,12,12-TETRACYANO-9,10-ANTHRAQUINODIMETHANE, HETEROACENES, CONJUGATED POLYMERS, TETRACYANOQUINODIMETHANE, CHARGE-TRANSFER, DERIVATIVES, pi-Extended TCNQ-based molecules, ELECTRON-ACCEPTORS",

author = "Baranov, {Denis S.} and Krivenko, {Olga L.} and Kazantsev, {Maxim S.} and Nevostruev, {Danil A.} and Kobeleva, {Elena S.} and Zinoviev, {Vladimir A.} and Dmitriev, {Alexey A.} and Gritsan, {Nina P.} and Kulik, {Leonid V.}",

year = "2019",

month = sep,

day = "1",

doi = "10.1016/j.synthmet.2019.06.013",

language = "English",

volume = "255",

journal = "Synthetic Metals",

issn = "0379-6779",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of 2,2′-[2,2′-(arenediyl)bis(anthra[2,3-b]thiophene-5,10-diylidene)]tetrapropanedinitriles and their performance as non-fullerene acceptors in organic photovoltaics

AU - Baranov, Denis S.

AU - Krivenko, Olga L.

AU - Kazantsev, Maxim S.

AU - Nevostruev, Danil A.

AU - Kobeleva, Elena S.

AU - Zinoviev, Vladimir A.

AU - Dmitriev, Alexey A.

AU - Gritsan, Nina P.

AU - Kulik, Leonid V.

PY - 2019/9/1

Y1 - 2019/9/1

N2 - Three novel molecules based on thiophene-fused 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) units linked through functionalized π-conjugated arene bridges are synthesized by three-step sequence of Sonagashira coupling, double thioannulation and Knoevenagel condensation. The energy of their frontier orbitals shows that these molecules are suitable for replacing fullerenes as electron acceptors in composites with conjugated donor polymers used in organic photovoltaics (OPV). The composite of polymer donor PCDTBT with fluorene-linked thiophene-fused TCAQs demonstrates good solubility in organic solvents and bulk heterojunction morphology with characteristic donor and acceptor domain size of several tens of nanometers, favourable for photoelectric conversion. This composite also exhibits prominent light-induced EPR signal indicating efficient photoinduced free charge generation. OPV devices based on this composite were fabricated by vacuum-free method. They show photoelectric conversion with maximum PCE of 0.71%.

AB - Three novel molecules based on thiophene-fused 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) units linked through functionalized π-conjugated arene bridges are synthesized by three-step sequence of Sonagashira coupling, double thioannulation and Knoevenagel condensation. The energy of their frontier orbitals shows that these molecules are suitable for replacing fullerenes as electron acceptors in composites with conjugated donor polymers used in organic photovoltaics (OPV). The composite of polymer donor PCDTBT with fluorene-linked thiophene-fused TCAQs demonstrates good solubility in organic solvents and bulk heterojunction morphology with characteristic donor and acceptor domain size of several tens of nanometers, favourable for photoelectric conversion. This composite also exhibits prominent light-induced EPR signal indicating efficient photoinduced free charge generation. OPV devices based on this composite were fabricated by vacuum-free method. They show photoelectric conversion with maximum PCE of 0.71%.

KW - Functionalized anthra[2,3-b]thiophenes

KW - Non-fullerene acceptors

KW - Photovoltaic properties

KW - Synthesis

KW - π-Extended TCNQ-based molecules

KW - DESIGN

KW - ACENES

KW - SEMICONDUCTORS

KW - 11,11,12,12-TETRACYANO-9,10-ANTHRAQUINODIMETHANE

KW - HETEROACENES

KW - CONJUGATED POLYMERS

KW - TETRACYANOQUINODIMETHANE

KW - CHARGE-TRANSFER

KW - DERIVATIVES

KW - pi-Extended TCNQ-based molecules

KW - ELECTRON-ACCEPTORS

UR - http://www.scopus.com/inward/record.url?scp=85067611919&partnerID=8YFLogxK

U2 - 10.1016/j.synthmet.2019.06.013

DO - 10.1016/j.synthmet.2019.06.013

M3 - Article

AN - SCOPUS:85067611919

VL - 255

JO - Synthetic Metals

JF - Synthetic Metals

SN - 0379-6779

M1 - 116097

ER -

ID: 20641192