Air-stable, high performance, rigid [:4,5]thieno[2,3-d]thiophene-derivative organic semiconductors

COMP 49

Joshua Schrier, jschrier@lbl.gov1, Sule Atahan, atahan@fas.harvard.edu2, Lin-Wang Wang, lwwang@lbl.gov1, and Alán Aspuru-Guzik, aspuru@chemistry.harvard.edu2. (1) Computational Research Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Mailstop 50F-1650, Berkeley, CA 94720, (2) Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138
There is a wide interest in finding new high performance, air-stable organic semiconductors for applications including organic field effect transistors (OFETs) and organic photovoltaics. Stimulated by recent experimental work on naphtho[2,3-b]naphtho[2',3':4,5]thieno[2,3-d]thiophene, which has demonstrated stability in air and relatively high (2-3 cm^2/V.s) hole mobility, we have computationally explored a number of related compounds using a combination of density-functional theory and molecular mechanics simulations. We predict that anthra[2,3-b]anthra[2',3':4,5]thieno[2,3-d]thiophene and pyreno[1,2-b]pyreno[2',1':4,5]thieno[2,3-d]thiophene will have hole mobilities, up to three times as the naptho compound, twice as high as pentacene, and will be stable in air. Moreover, analysis of the HOMO levels indicates that these can be substituted for tetracene in C60/tetracene/PEDOT:ITO organic photovoltaics, where the air stability and greatly improved hole mobilities will dramatically increase the performance of these devices.

This work was supported by the U. S. Department of Energy under Contract No. DE-AC03-76SF00098 and the Faculty of Arts and Sciences of Harvard University and the Henry Beck Fund at the Harvard Center for the Environment.

 

Quantum Chemistry
1:30 PM-4:15 PM, Sunday, August 19, 2007 BCEC -- 162A, Oral

Division of Computers in Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007