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

被引：5
作者：
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 ]
机构：
[1] Russian Acad Sci, VV Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Novosibirsk 630090, Russia
[3] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
[4] Russian Acad Sci, Nikolaev Inst Inorgan Chem, Siberian Branch, Novosibirsk 630090, Russia
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 19期
基金：
俄罗斯科学基金会;
关键词：
Functional organic materials; Fused-ring systems; Sulfur heterocycles; Polycycles; Quinones; Annulation; Electron-deficient compounds; ASYMMETRIC LINEAR ACENES; NON-FULLERENE ACCEPTORS; ACETYLENIC DERIVATIVES; ORGANIC SEMICONDUCTORS; SMALL MOLECULES; BASIS-SETS; PERFORMANCE; DESIGN; POLYMERS; SULFUR;
D O I：
10.1002/ejoc.201800275
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：2259 / 2266
页数：8
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