Tetradehydrodinaphtho[10]annulene and its transformation into zethrene: A hitherto unknown dehydroannulene and a forgotten aromatic hydrocarbon

Umeda, Rui; Hibi, Daijiro; Miki, Koji; Tobe, Yoshito

doi:10.1351/PAC-CON-09-10-12

Pure Appl. Chem., 2010, Vol. 82, No. 4, pp. 871-878

http://dx.doi.org/10.1351/PAC-CON-09-10-12

Published online 2010-03-10

Tetradehydrodinaphtho[10]annulene and its transformation into zethrene: A hitherto unknown dehydroannulene and a forgotten aromatic hydrocarbon

Rui Umeda, Daijiro Hibi, Koji Miki and Yoshito Tobe*

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan

Abstract: The synthesis and structural characterization of a hitherto unknown tetradehydro-dinaphtho[10]annulene, which had eluded isolation since attempts initiated during the late 1960s, was achieved. Moreover, the dehydroannulene was transformed into stable derivatives of zethrene, which was first reported in 1955, but forgotten for a long time. These molecules are substituted at the 7,14-positions and open the door to the zethrene family for potential application as optoelectronic materials.