Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

Beilstein Journal of Organic Chemistry

Olaf M. Magnussen¹  Talina Rusch¹  Roland Löw²  Tobias Moje²  Fynn Röhricht²  Rainer Herges² 

[1] Institute for Experimental and Applied Physics, University of Kiel, Leibnizstraße 19, 24098 Kiel, Germany;Otto Diels Institute for Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany;

关键词: [2 + 2] cycloaddition;    [2 + 2] cycloreversion;    norbornadiene;    photochemical isomerization;    quadricyclane;    self-assembled monolayers;    TATA platform;    thermal isomerization;    TOTA platform;   

DOI  :  10.3762/bjoc.15.175

来源: DOAJ

【 摘 要 】

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 cis→trans 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).

【 授权许可】

Unknown