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

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

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research