Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
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DOI：
10.1038/s41467-020-15210-2
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发表时间：
2020-03
影响因子：
16.6
通讯作者：
A. Riss;Marcus Richter;A. P. Paz;Xiao-Ye Wang;R. Raju;Yuanqing He;J. Ducke;Eduardo Corral
中科院分区：
文献类型：
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作者：
A. Riss;Marcus Richter;A. P. Paz;Xiao-Ye Wang;R. Raju;Yuanqing He;J. Ducke;Eduardo Corral
有机材料在电子、光电子和自旋电子器件中的巨大潜力使得人们对直接在绝缘界面处具有定制功能的π共轭体系的制造产生了极大的兴趣。这种材料在非金属表面上的表面制造仍有待证明具有高产率和选择性。在这里，我们提出了在金属基底上，绝缘层，和在固态下的多环芳烃链的合成。扫描探针显微镜显示azaullazine重复单元在Au（111）、Ag（111）和h-BN/Cu（111）上的形成，源于通过CN取代的多环芳香族偶氮甲碱叶立德（PAMY）中间体的环加成反应随后脱氢的分子间均偶联。基质辅助激光解吸/电离（MALDI）质谱表明，反应也发生在固态下，没有任何催化剂。这种分子间环加成反应是在任意绝缘表面上直接合成区域规整聚芳族聚合物的有前途的方法。
The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of π-conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains to be demonstrated with high yield and selectivity. Here we present the synthesis of polyaromatic chains on metallic substrates, insulating layers, and in the solid state. Scanning probe microscopy shows the formation of azaullazine repeating units on Au(111), Ag(111), and h-BN/Cu(111), stemming from intermolecular homo-coupling via cycloaddition reactions of CN-substituted polycyclic aromatic azomethine ylide (PAMY) intermediates followed by subsequent dehydrogenation. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry demonstrates that the reaction also takes place in the solid state in the absence of any catalyst. Such intermolecular cycloaddition reactions are promising methods for direct synthesis of regioregular polyaromatic polymers on arbitrary insulating surfaces.