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

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

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2018, Volume: 2018, Number: 19, Pages: 2259-2266 Pages count : 8 DOI: 10.1002/ejoc.201800275

Tags

Functional organic materials; Fused-ring systems; Sulfur heterocycles; Polycycles; Quinones; Annulation; Electron-deficient compounds

Authors

Baranov Denis S. ^1,2 , Uvarov Mikhail N. ¹ , Kazantsev Maxim S. ^2,3 , Glebov Evgeni M. ^1,2 , Nevostruev Danil A. ¹ , Mostovich Evgeny A. ^2,3 , Antonova Olga V. ⁴ , Kulik Leonid V. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, VV Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) Russian Acad Sci, Nikolaev Inst Inorgan Chem, Siberian Branch, Novosibirsk 630090, Russia

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 -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.

Baranov D.S. , Uvarov M.N. , Kazantsev M.S. , Glebov E.M. , Nevostruev D.A. , Mostovich E.A. , Antonova O.V. , Kulik L.V.
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. V.2018. N19. P.2259-2266. DOI: 10.1002/ejoc.201800275 WOS Scopus РИНЦ

Published online:	May 17, 2018
Published print:	May 24, 2018

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