The on‐surface synthesis of an isomer of undecacene, bearing two four‐membered rings and two para‐quinodimethane moieties, starting from a tetramethyl‐substituted diepoxy precursor, is presented. The transformation implies a thermal double deoxygenation followed by a stepwise double dehydrogenation reaction on the Au(111) surface, locally induced by inelastic tunneling electrons. This results in the transformation of para‐dimethylbenzene moieties into non‐aromatic para‐quinodimethanes. The structures and electronic properties of the intermediate and final products are investigated at the single molecule level with high spatial resolution, using both scanning tunneling microscopy/spectroscopy and non‐contact atomic force microscopy. The experimental results are supported by density functional theory calculations.

中文翻译：

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表面逐步双重脱氢形成含对醌二甲烷的十一碳烯异构体


提出了从四甲基取代的二环氧前体开始的十一碳烯异构体的表面合成，该异构体带有两个四元环和两个对醌二甲烷部分。该转变意味着在 Au(111) 表面上发生热双脱氧反应，然后由非弹性隧道电子局部诱导逐步发生双脱氢反应。这导致对二苯部分转化为非芳香族对醌二甲烷。使用扫描隧道显微镜/光谱学和非接触原子力显微镜在单分子水平上以高空间分辨率研究中间产物和最终产物的结构和电子性质。实验结果得到了密度泛函理论计算的支持。