Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

被引：66

作者：

Berger, Reinhard ^{[1
]}

Wagner, Manfred ^{[1
]}

Feng, Xinliang ^{[1
,2
]}

Muellen, Klaus ^{[1
]}

机构：

[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany

[2] Tech Univ Dresden, Chair Mol Funct Mat, D-01062 Dresden, Germany

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 01期

关键词：

CRYSTAL-STRUCTURE; ULLAZINE; 1,3-DIPOLES; REACTIVITY; MOLECULES;

D O I：

10.1039/c4sc02793k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Based on polycyclic aromatic azomethine ylides (PAMYs), a metal-free "cycloaddition-planarization-sequence" is proposed, providing a unique entry to extended nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). This method is highly versatile, as the structure of unprecedented N-PAHs can be tailored by the dipolarophile in the crucial 1,3-cycloaddition-reaction. Linear, as well as five- and six-membered cyclic dipolarophiles are successfully used. The geometric and optoelectronic nature of N-PAHs are investigated by UV-vis absorption and single crystal structure analysis. Remarkably, the newly synthesized N-PAHs demonstrate varying absorption profiles, covering the whole visible light range with rich photophysical properties, for example, fluorescent quantum yields up to 54%.

引用

页码：436 / 441

页数：6

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