Synthesis and explosive decomposition of organometallic dehydro[18]annulenes: an access to carbon nanostructures.
The synthesis of eight new cyclobutadiene or ferrocene-fused organometallic dehydroannulenes is reported. Cadiot-type coupling of a 1-bromoethynyl-2-silylethynylbenzene derivative to an organometallic diyne (1,2-diethynyl-3,4-bis(trimethylsilyl)cyclobutadiene(cyclopentadienyl )cobalt or 1,2-diethynylferrocene) is followed by deprotection and Cu(OAc)(2)-promoted ring closure. Five of the organometallic dehydroannulenes were structurally characterized. Three of the novel cycles explode at temperatures from 196 to 293 degrees C and form insoluble carbon materials. The soot produced from 13a shows a high abundance of onion-like carbon nanostructures. The nanostructures were characterized by high-resolution transmission electron microscopy.
Laskoski
Matthew
M
USC NanoCenter and the Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA.
Steffen
Winfried
W
Morton
Jason G M
JG
Smith
Mark D
MD
Bunz
Uwe H F
UH