Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

• Roland Löw,
• Talina Rusch,
• Tobias Moje,
• Fynn Röhricht,
• Olaf M. Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

• ; quadricyclane; self-assembled monolayers; TATA platform; thermal isomerization; TOTA platform; Introduction Recently, we discovered that the thermochemically forbidden cis–trans isomerization of azobenzenes can be efficiently catalysed by a very peculiar mechanism on bulk gold [1]. In heterogeneous catalysis

• arrangement of the phenyl group and the double bond of the NBD unit and thus lowers the conjugation. We also synthesized the corresponding system directly connected to a TOTA platform 3. Functionalized TOTA molecules are more stable than the corresponding TATA systems and usually can be sublimed without

• -cyanonorbornadiene (4) was subjected to halogen–metal exchange with n-BuLi and coupled with the central atom of the TOTA platform 8 to obtain the norbornadiene-functionalized TOTA platform 3 (22%, Scheme 1). The synthesis of the corresponding TATA platform including an additional 2-methylphenyl group (2) was