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Synthesis of Functionalized Triazatriangulenes for Application in Photo‐Switchable Self‐Assembled Monolayers
Author(s) -
Kubitschke Jens,
Näther Christian,
Herges Rainer
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000650
Subject(s) - azobenzene , chemistry , isomerization , monolayer , linker , molecule , nucleophile , self assembly , self assembled monolayer , nucleophilic addition , ion , in situ , combinatorial chemistry , photochemistry , stereochemistry , organic chemistry , catalysis , biochemistry , computer science , operating system
Abstract 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