AMPC  Vol.2 No.3 , September 2012
Substituted Molecular p-Dopants: A Theoretical Study
Abstract: Conductivity dopants with processing properties suitable for industrial applications are of importance to the organic electronics field. However, the number of commercially available organic molecular dopants is limited. The electron acceptor 2,3,5,6-tetrafluoro-7,7,8,8,-tetracyanoquinodimethane (F4-TCNQ) is the most utilized P-dopant; however, it has high volatility and a poor sticking coefficient, which makes it difficult to control doping levels and prevent vacuum system contamination. A design concept for P-type molecular dopants based on the TCNQ core which are substituted to improve processing properties without sacrificing the electronic properties necessary is presented. The correlation between the lowest unoccupied molecular orbital (LUMO) energy and the position of substitution as well as the choice of linker is evaluated. The position of substitution as well as the choice of linker has a significant effect on the electronic properties. However, the geometry of the substituted molecules was not significantly distorted from that of the parent F4-TCNQ, and the electron density was delocalized on the TCNQ core. We also put forward four possible molecular dopants with suitable energy levels.
Cite this paper: A. Padmaperuma, "Substituted Molecular p-Dopants: A Theoretical Study," Advances in Materials Physics and Chemistry, Vol. 2 No. 3, 2012, pp. 163-172. doi: 10.4236/ampc.2012.23025.

[1]   K. Walzer, B. Maennig, M. Pfeiffer, K Leo, Chem. Rev. 107, (2007) 1233. doi:10.1021/cr050156n

[2]   X. Zhou, M. Pfeiffer, J. Blochwitz, A. Werner, A. Nollau, T. Fritz, K. Leo, Appl. Phys. Lett. 73, (2001) 3202. doi:10.1063/1.1343849

[3]   B.X. Mi, Z.Q. Gao, K.W. Cheah, C.H. Chen, Appl. Phys. Lett. 94, (2009), 073507. doi:10.1063/1.3073719

[4]   W. Gao, A. Kahn, Org. Elect. 3, (2002), 53. doi:10.1016/S1566-1199(02)00033-2

[5]   C. Williams, L. Sergey, J. Ferraris, A.A. Zakhidov, J. of Luminescence, 110, (2004), 396. doi:10.1016/j.jlumin.2004.08.038

[6]   M. Valiev, E.J. Bylaska, N. Govind, K. Kowalski, T.P. Straatsma, H.J.J. van Dam, D. Wang, J. Nieplocha, E. Apra, T.L. Windus, W.A. de Jong, Comput. Phys. Commun. 181, (2010), 1477. doi:10.1016/j.cpc.2010.04.018

[7]   A.D. Becke, Phys. Rev. A, 38, (1988), 3098.; J. P. Perdew, Phys. Rev. B, 33, (1986), 8822.; C. Lee, W. Yang, R.G. Parr, Phys. Rev. B. 37, (1988), 785. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157, (1989), 200. A.D. Becke, J. Chem. Phys. 98, (1993), 5648. doi:10.1063/1.464913

[8]   P.K. Koech, L.S. Sapochak, J.E. Rainbolt, L. Cosimbescu, E. Polikarpov, J.S. Swensen, L. Wang, A.B. Padmaperuma, D.J. Gaspar, Organic Light Emitting Materials and Devices XIII, Proc. SPIE 7415, (2009), 741505. doi:10.1117/12.827298

[9]   L. Cosimbescu, A.B. Padmaperuma, D.J. Gaspar, J. Phys. Chem. A, 115, (2011) 13498. doi:10.1021/jp2005869

[10]   T. Koopmans, Physica, 1, (1933), 104. doi:10.1016/S0031-8914(34)90011-2

[11]   R. A. Kendall, T.H. Dunning, R.J. Harrison, J. Chem. Phys. 96, (1992), 6796. doi:10.1063/1.462569

[12]   B. Milián, R. Pou-Ame’rigo, R. Viruela, E. Orti, Journal of Molecular Structure (Theochem), 709, (2004), 97. doi:10.1016/j.theochem.2003.09.011

[13]   See Supporting information for a complete list

[14]   J.E. Rainbolt, P.K. Koech, J.S. Swensen, E. Polikarpov, A. Von Ruden, L. Wang, L. Cosimbescu, L.S. Sapochak, A.B. Padmaperuma, D.J. Gaspar, Manuscript in preparation for J. Mat. Chem. (2012).

[15]   J.S. Swensen, L. Wang, J.E. Rainbolt, P.K. Koech, E. Polikarpov, A.B. Padmaperuma, D.J. Gaspar, Manuscript Submitted to Org. Elec. (2012). doi:10.1016/j.orgel.2012.07.045

[16]   Black, G.; Daily, J.; Didi-er, B.; Elsethagen, T.; Feller, D.; Gracio, D.; Hackler, M.; Havre, S.; Jones, D.; Jurrus, E.; Keller, T.; Lansing, C.; Matsumoto, S.; Palmer, B.; Peterson, M.; Schuchardt, K.; Stephan, E.; Sun, L.; Swanson, K.; Taylor, H.; Thomas, G.; Vorpagel, E.; Windus, T.; Winters, C.; "ECCE, A Problem Solving Environment for Computational Chemistry, Software Version 4.5.1", Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA, (2007).