结合烁尔反应和亲核芳香族氢取代 (SNH) 两步合成基于 [1,2,5]oxadiazolo[3,4-b]quinoxaline 的新型融合体系

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-07-26 DOI:10.1007/s11172-024-4281-z

E. M. Krynina, Yu. A. Kvashnin, D. A. Gazizov, M. I. Kodess, M. A. Ezhikova, G. L. Rusinov, E. V. Verbitskiy, V. N. Charushin

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引用次数: 0

摘要

基于氢的亲核芳香取代和肖尔交叉耦合的顺序，我们开发出了一种以[1,2,5]噁二唑啉-[3,4-b]喹喔啉为骨架的贫乏多环系统的简单合成路线。根据电化学和光物理测量数据，合成的化合物有可能被视为窄间隙（从 1.97 到 2.34 eV）n 型有机半导体，其能级与市售顶级电子半导体的能级相当。

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Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (SNH)

A simple synthetic route to poorly available polycyclic systems with a [1,2,5]oxadiazolo-[3,4-b]quinoxaline backbone has been developed, which is based on the sequence of nucleophilic aromatic substitution of hydrogen and the Scholl cross-coupling. According to the data from electrochemical and photophysical measurements, the synthesized compounds can be potentially considered as the narrow-gap (from 1.97 to 2.34 eV) n-type organic semiconductors, the energy levels of which are comparable to those of top commercially available electronic semiconductors.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.