Löw Roland, Rusch Talina, Moje Tobias, Röhricht Fynn, Magnussen Olaf M, Herges Rainer
Otto Diels Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany.
Institute for Experimental and Applied Physics, University of Kiel, Leibnizstraße 19, 24098 Kiel, Germany.
Beilstein J Org Chem. 2019 Jul 30;15:1815-1821. doi: 10.3762/bjoc.15.175. eCollection 2019.
Triazatriangulenium (TATA) and trioxatriangulenium (TOTA) ions are particularly suited systems to mount functional molecules onto atomically flat surfaces such as Au(111). The TATA and TOTA units serve as platforms that absorb onto the surface and form ordered monolayers, while the functional groups are protruding upright and freestanding from the central carbon atoms. Azobenzene derivatized TATA's are known to exhibit extremely fast → isomerization on metal surfaces, via a peculiar non-adiabatic singlet→triplet→singlet mechanism. We now prepared norbornadienes (NBD) and quadricyclanes (QC) attached to TATA and TOTA platforms which can be used to check if these accelerated rates and the spin change mechanism also apply to [2 + 2] cycloreversions (QC→NBD).
三氮杂三角烯鎓（TATA）和三氧杂三角烯鎓（TOTA）离子是特别适合将功能分子固定在诸如Au(111)等原子级平整表面上的体系。TATA和TOTA单元作为吸附在表面并形成有序单层的平台，而官能团则从中心碳原子垂直突出且独立存在。已知偶氮苯衍生的TATA在金属表面通过一种特殊的非绝热单重态→三重态→单重态机制表现出极快的异构化。我们现在制备了连接到TATA和TOTA平台上的降冰片二烯（NBD）和四环烷（QC），它们可用于检验这些加速速率和自旋变化机制是否也适用于[2 + 2]环化逆转（QC→NBD）。
