Covalent and noncovalent assemblies dehydrobenzoannulenes

ORGN 660

Yoshito Tobe, tobe@chem.es.osaka-u.ac.jp, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, 560-8531, Japan
Dehydrobenzoannules (DBAs) play a central role in the chemistry of carbon-rich compounds as scaffolds of optoelectronic materials and two-dimensional all-carbon networks. We are interested in the properties arising from the assembly of such motifs with covalent or noncovalent interactions. Herein we report the synthesis and molecular structure of twisted, propeller-shaped tris([14]DBA) 1 as an example of covalent assembly of DBAs. For noncovalent assembly of DBAs, two-dimensional self-assembly of DBA derivatives, such as 2 and 3, at the graphite-solvent interface will be presented. Novel two-dimensional networks were observed through the STM experiments, depending on the shape and size of the pi-electron system, length of the alkyl chains, and the solvents.