A one-step synthesis of a poly(iptycene) through an unusual Diels-Alder cyclization/dechlorination of tetrachloropentacene.
We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels-Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600-900 degrees C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.
Perepichka
Dmitrii F
DF
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Bendikov
Michael
M
Meng
Hong
H
Wudl
Fred
F