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A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐ b ]thiophene‐6‐ylidene)]dipropanedinitriles
Author(s) -
Baranov Denis S.,
Uvarov Mikhail N.,
Kazantsev Maxim S.,
Glebov Evgeni M.,
Nevostruev Danil A.,
Mostovich Evgeny A.,
Antonova Olga V.,
Kulik Leonid V.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800275
Subject(s) - thiophene , chemistry , knoevenagel condensation , cyclic voltammetry , electron paramagnetic resonance , photochemistry , electron acceptor , conjugated system , molecule , spectroscopy , annulation , polymer chemistry , polymer , organic chemistry , electrochemistry , catalysis , physics , electrode , nuclear magnetic resonance , quantum mechanics
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.