10-04 :: April 2010
News in Brief
Organic Electronics //
Molecule With Promising Semiconductor Properties
including two UNH undergraduates, from the Uni- versity of New Hampshire, USA, has synthesized the
first-ever stable derivative of nonacene, creating a
compound that holds significant promise in the ma- nufacture of flexible organic electronics such as large displays, solar cells and radio frequency identification tags.
Nonacene, a compound with nine rings of benzene fused in a linear fashion, belongs to a class of organic semiconductors called acenes, widely recognized to be among the very best in terms of electronic perfor- mance. Yet they are highly unstable – they oxidize rapidly.
“We have known that nonacene would have very desirable electronic properties, but it was just a tease, because you couldn’t make it, you couldn’t use it,” says Miller, who has been working to prepare large acenes since 2007.
Miller and his team – research scientist Irvinder Kaur, postdoctoral fellow Mikael Jazdzyk, and UNH se- niors Polina Prusevich and Nathan Stein – built the large nonacene derivative from smaller pieces, the way one might build a Lego structure. The key to
the molecule’s stability is the addition of arylthio
functional groups, stable collections of atoms that
team of chemists led by professor of organic chemistry and materials science Glen Miller and
contain sulfur. “The skeleton of the molecule is still there, but it’s got additional functional groups at- tached to the skeleton,” says Miller. This not only made the derivative stable, it also made it soluble, further enhancing its usefulness.
“Before our work, the thought of preparing flexi- ble organic electronic devices using nonacene or a nonacene derivative was just a dream,” he adds. “With this major step forward, we are much closer to realizing the dream.”
Irvinder Kaur, Mikael Jazdzyk, Nathan N. Stein, Polina Pru- sevich and Glen P. Miller: Design, Synthesis, and Characte- rization of a Persistent Nonacene Derivative, In: Journal of
the American Chemical Society (JACS), Vol. 132(2010), Is-
sue 4, February 3, 2010, Pages 1261-1263, DOI:10.1021/ ja9095472: