Synthesis of Functionalized Triazatriangulenes for Application in Photo-Switchable Self-Assembled Monolayers

Various triazatriangulenes are synthesized by nucleophilic attack at the central C atom of triazatriangulenium ions. The molecular functions, especially azobenzenes, are fixed via an ethynyl linker by in situ deprotection of trimethylsilylalkynes. The structure of two of these molecules is further investigated by X‐ray crystallography. The photo‐induced trans/cis‐isomerization of the azobenzene substituted derivatives is analyzed in solution and shows great promise for the preparation of switchable functionalized monolayers, as the triazatriangulenes are known for their self‐assembly on gold surfaces.1 The synthesis of functionalized triazatriangulenes is presented and the trans/cis isomerization of azobenzene derivatives in solution is investigated. The described attachment of various molecular functions to the TATA platform represents a modular system for the formation of switchable SAMs.