Berger Reinhard, Wagner Manfred, Feng Xinliang, Müllen Klaus
Max-Planck-Institut für Polymerforschung , Ackermannweg 10 , 55128 Mainz , Germany . Email:
Chair for Molecular Functional Materials , Technische Universität Dresden , 01062 Dresden , Germany . Email:
Chem Sci. 2015 Jan 1;6(1):436-441. doi: 10.1039/c4sc02793k. Epub 2014 Oct 22.
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%.
基于多环芳香偶氮甲碱叶立德（PAMYs），提出了一种无金属的“环加成-平面化序列”，为扩展含氮多环芳烃（N-PAHs）提供了独特的途径。该方法具有高度的通用性，因为在关键的1,3-环加成反应中，前所未有的N-PAHs的结构可以通过亲偶极体进行定制。线性以及五元、六元环状亲偶极体均被成功使用。通过紫外-可见吸收和单晶结构分析研究了N-PAHs的几何和光电性质。值得注意的是，新合成的N-PAHs表现出不同的吸收光谱，覆盖了整个可见光范围，具有丰富的光物理性质，例如荧光量子产率高达54%。
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