N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines

被引：25

作者：

Sekine, Kohei ^{[1
]}

Stuck, Fabian ^{[1
]}

Schulmeister, Juergen ^{[1
]}

Wurm, Thomas ^{[1
]}

Zetschok, Dominik ^{[1
]}

Rominger, Frank ^{[1
]}

Rudolph, Matthias ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 48期

关键词：

annulation; diynes; gold catalysis; heterocycles; pentalenes; FIELD-EFFECT TRANSISTORS; ORGANIC SEMICONDUCTORS; ACTIVATION; PLATINUM; ALKYNES; ROUTE;

D O I：

10.1002/chem.201803096

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gold-catalyzed annulation of diethynyl N-heterocycles for the synthesis of quinoxaline-/phenazine-based pentalenes and the study of their optoelectronic properties are described. The inhibition of the gold catalyst by the nitrogen centers in the substrate and the product could be overcome by increasing the reaction temperature to 130 degrees C, which usually leads to catalyst decomposition in gold catalysis. At 130 degrees C, 6,7-di(arylethynyl)quinoxalines in chlorobenzene give the corresponding pentalenes. The annulation of 2,3-di(arylethynyl)quinoxalines requires an even higher temperature under microwave irradiation. The quinoxaline-based pentalenes showed lower LUMO levels compared to the corresponding naphthalene-based pentalenes.

引用

页码：12515 / 12518

页数：4

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