Synthesis and Optical Properties of Diaza- and Tetraazatetracenes

被引：59

作者：

Lindner, Benjamin D. ^{[1
]}

Engelhart, Jens U. ^{[1
]}

Maerken, Michaela ^{[1
]}

Tverskoy, Olena ^{[1
]}

Appleton, Anthony L. ^{[2
]}

Rominger, Frank ^{[1
]}

Hardcastle, Kenneth I. ^{[3
]}

Enders, Markus ^{[4
]}

Bunz, Uwe H. F. ^{[1
]}

机构：

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

[2] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[3] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

[4] Heidelberg Univ, Anorgan Chem Inst, D-69120 Heidelberg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 15期

基金：

美国国家科学基金会;

关键词：

alkynes; diamines; heterocycles; palladium; tetracenes; SUBSTITUTION; ACENES; FLUOROPHORES; ORIENTATION;

D O I：

10.1002/chem.201103227

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of functionalized diaza- and tetraazatetracenes was synthesized, either by condensation of an aromatic diamine with an ortho-quinone/diethyloxalate followed by chlorination with POCl3 to give diazatetracenes or by palladium-catalyzed coupling of a phenylenediamine with various 2,3-dichloroquinoxalines to give tetraazatetracenes (after oxidation with MnO2). Representative examples included halogenated and nitrated derivatives. The optical properties of these azatetracenes were discussed with respect to their molecular structures and substitution patterns. The diazatetracenes and tetraazatetracenes formed two different groups that had significantly different electronic structures and properties. Furthermore, 1,2,3,4-tetrafluoro-6,11-bis((triisopropylsilyl)ethynyl)benzo[b]phenazine was synthesized, which is the first reported fluorinated diazatetracene. Single-crystal X-ray analysis of this compound is reported.

引用

页码：4627 / 4633

页数：7

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