A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles

Denis S. Baranov; Mikhail N. Uvarov; Maxim S. Kazantsev; Evgeni M. Glebov; Danil A. Nevostruev; Evgeny A. Mostovich; Olga V. Antonova; Leonid V. Kulik

doi:10.1002/ejoc.201800275

A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles

Denis S. Baranov, Mikhail N. Uvarov, Maxim S. Kazantsev, Evgeni M. Glebov, Danil A. Nevostruev, Evgeny A. Mostovich, Olga V. Antonova, Leonid V. Kulik

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

4 Citations (Scopus)

Abstract

A concise organolithium-free route to build electron-accepting molecules consisting of two 2-(11-oxoanthra[1,2-b]thiophen-6-ylidene)propanedinitrile units connected by functionalized π-conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron-accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light-induced electron transfer in their blend with a donor polymer, poly(3-hexylthiophene-2,5-diyl), detected by electron paramagnetic resonance spectroscopy.

Original language	English
Pages (from-to)	2259-2266
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201800275
Publication status	Published - 24 May 2018

Keywords

Annulation
Electron-deficient compounds
Functional organic materials
Fused-ring systems
Polycycles
Quinones
Sulfur heterocycles
PERFORMANCE ORGANIC SEMICONDUCTORS
SOLAR-CELLS
SMALL MOLECULES
NON-FULLERENE ACCEPTORS
LIGHT-INDUCED EPR
FIELD-EFFECT TRANSISTORS
ASYMMETRIC LINEAR ACENES
ACETYLENIC DERIVATIVES
BASIS-SETS
SODIUM SULFIDE

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10.1002/ejoc.201800275

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Baranov, D. S., Uvarov, M. N., Kazantsev, M. S., Glebov, E. M., Nevostruev, D. A., Mostovich, E. A., Antonova, O. V., & Kulik, L. V. (2018). A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles. European Journal of Organic Chemistry, 2018(19), 2259-2266. https://doi.org/10.1002/ejoc.201800275

Baranov, Denis S. ; Uvarov, Mikhail N. ; Kazantsev, Maxim S. ; Glebov, Evgeni M. ; Nevostruev, Danil A. ; Mostovich, Evgeny A. ; Antonova, Olga V. ; Kulik, Leonid V. / A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 19. pp. 2259-2266.

@article{dd1648a23bd942d0884284fda4ae7636,

title = "A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles",

abstract = "A concise organolithium-free route to build electron-accepting molecules consisting of two 2-(11-oxoanthra[1,2-b]thiophen-6-ylidene)propanedinitrile units connected by functionalized π-conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron-accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light-induced electron transfer in their blend with a donor polymer, poly(3-hexylthiophene-2,5-diyl), detected by electron paramagnetic resonance spectroscopy.",

keywords = "Annulation, Electron-deficient compounds, Functional organic materials, Fused-ring systems, Polycycles, Quinones, Sulfur heterocycles, PERFORMANCE ORGANIC SEMICONDUCTORS, SOLAR-CELLS, SMALL MOLECULES, NON-FULLERENE ACCEPTORS, LIGHT-INDUCED EPR, FIELD-EFFECT TRANSISTORS, ASYMMETRIC LINEAR ACENES, ACETYLENIC DERIVATIVES, BASIS-SETS, SODIUM SULFIDE",

author = "Baranov, {Denis S.} and Uvarov, {Mikhail N.} and Kazantsev, {Maxim S.} and Glebov, {Evgeni M.} and Nevostruev, {Danil A.} and Mostovich, {Evgeny A.} and Antonova, {Olga V.} and Kulik, {Leonid V.}",

year = "2018",

month = may,

day = "24",

doi = "10.1002/ejoc.201800275",

language = "English",

volume = "2018",

pages = "2259--2266",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "19",

}

A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles. / Baranov, Denis S.; Uvarov, Mikhail N.; Kazantsev, Maxim S.; Glebov, Evgeni M.; Nevostruev, Danil A.; Mostovich, Evgeny A.; Antonova, Olga V.; Kulik, Leonid V.

In: European Journal of Organic Chemistry, Vol. 2018, No. 19, 24.05.2018, p. 2259-2266.

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

TY - JOUR

T1 - A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles

AU - Baranov, Denis S.

AU - Uvarov, Mikhail N.

AU - Kazantsev, Maxim S.

AU - Glebov, Evgeni M.

AU - Nevostruev, Danil A.

AU - Mostovich, Evgeny A.

AU - Antonova, Olga V.

AU - Kulik, Leonid V.

PY - 2018/5/24

Y1 - 2018/5/24

N2 - A concise organolithium-free route to build electron-accepting molecules consisting of two 2-(11-oxoanthra[1,2-b]thiophen-6-ylidene)propanedinitrile units connected by functionalized π-conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron-accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light-induced electron transfer in their blend with a donor polymer, poly(3-hexylthiophene-2,5-diyl), detected by electron paramagnetic resonance spectroscopy.

AB - A concise organolithium-free route to build electron-accepting molecules consisting of two 2-(11-oxoanthra[1,2-b]thiophen-6-ylidene)propanedinitrile units connected by functionalized π-conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron-accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light-induced electron transfer in their blend with a donor polymer, poly(3-hexylthiophene-2,5-diyl), detected by electron paramagnetic resonance spectroscopy.

KW - Annulation

KW - Electron-deficient compounds

KW - Functional organic materials

KW - Fused-ring systems

KW - Polycycles

KW - Quinones

KW - Sulfur heterocycles

KW - PERFORMANCE ORGANIC SEMICONDUCTORS

KW - SOLAR-CELLS

KW - SMALL MOLECULES

KW - NON-FULLERENE ACCEPTORS

KW - LIGHT-INDUCED EPR

KW - FIELD-EFFECT TRANSISTORS

KW - ASYMMETRIC LINEAR ACENES

KW - ACETYLENIC DERIVATIVES

KW - BASIS-SETS

KW - SODIUM SULFIDE

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U2 - 10.1002/ejoc.201800275

DO - 10.1002/ejoc.201800275

M3 - Article

AN - SCOPUS:85047667545

VL - 2018

SP - 2259

EP - 2266

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 19

ER -

A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles

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Keywords

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