Synthesis of isocoumarins and PAHs with electron-withdrawing substituents: Impact of the substituent nature on the photophysical behavior

被引：7

作者：

Arsenov, Mikhail A. ^{[1
]}

V. Fedorov, Yury ^{[1
]}

V. Muratov, Dmitry ^{[1
]}

V. Nelyubina, Yulia ^{[1
]}

Loginov, Dmitry A. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28, Moscow 119991, Russia

[2] GV Plekhanov Russian Univ Econ, 36 Stremyanny Per, Moscow 117997, Russia

来源：

DYES AND PIGMENTS | 2022年 / 206卷

基金：

俄罗斯科学基金会;

关键词：

Acenes; C-H activation; Fluorescence; Isocoumarins; Rhodium catalysis; AGGREGATION-INDUCED EMISSION; BENZOIC-ACIDS; CARBOXYLIC-ACIDS; ALKYNES; ANNULATION; COMPLEXES; CATALYST;

D O I：

10.1016/j.dyepig.2022.110653

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The efficient conditions for rhodium catalyzed oxidative coupling of electron-poor carboxylic acids with diphenylacetylene have been optimized. The best protocol uses Ag2CO3 as an oxidant and DMF as a solvent. The reactions smoothly proceed with the formation of isocoumarins and polycyclic aromatic hydrocarbons (PAHs). The isonicotinic, coumalic, coumarin-3-carboxylic, 4-nitrobenzoic, 4-cyanobenzoic, 4-(ethoxycarbonyl)benzoic, and terephthalic acids were successfully involved in the annulation. In contrast, in the case of picolinic acid, the formation of the stable chelate complex Cp*RhCl(O,N-pic) prohibits the catalytic reaction. The photophysical properties of isocoumarins and PAHs in solutions, such as fluorescence emission and solvatochromic effects, have been studied. In particular, the isocoumarin dyes demonstrate a phenomenon of aggregation-induced emission, while PAHs with electron-withdrawing substituents exhibit strong fluorescence emission in the violet region (370-390 nm) with quantum yields up to 55%.

引用

页数：12

共 45 条

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