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Theoretical Investigation of Structural Effects on the Charge Transfer Properties in Modified Phthalocyanines

Published online by Cambridge University Press:  28 December 2015

Patrick J. Dwyer  and
Stephen P. Kelty
Patrick J. Dwyer
Affiliation:
Center for Computational Research Department of Chemistry and Biochemistry, Seton Hall University South Orange, New Jersey, 07079, U.S.A.
Stephen P. Kelty*
Affiliation:
Center for Computational Research Department of Chemistry and Biochemistry, Seton Hall University South Orange, New Jersey, 07079, U.S.A.
*
*(Email: stephen.kelty@shu.edu)
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Abstract

For efficient charge separation and charge transport in optoelectronic materials, small internal reorganization energies are desired. While many p-type organic semiconductors have been reported with low internal reorganization energies, few n-type materials with low reorganization energy are known. Metal phthalocyanines have long received extensive research attention in the field of organic device electronics due to their highly tunable electronic properties through modification of the molecular periphery. In this study, density functional theory (DFT) calculations are performed on a series of zinc-phthalocyanines (ZnPc) with various degrees of peripheral per-fluoroalkyl (-C3F7) modification. Introduction of the highly electron withdrawing groups on the periphery leads to a lowering in the energy of the molecular frontier orbitals as well as an increase in the electron affinity. Additionally, all molecules studies are found to be most stable in their anionic form, demonstrating their potential as n-type materials. However, the calculated internal reorganization energy slightly increases as a function of peripheral modification. By varying the degree of modification we develop a strategy for obtaining an optimal balance between low reorganization energy and high electron affinity for the development of novel n-type optoelectronic materials.

Keywords

photovoltaicorganometallicthin film
Type
Articles
Information
MRS Advances , Volume 1 , Issue 7: Electronics and Photonics , 2016 , pp. 453 - 458
Copyright
Copyright © Materials Research Society 2015 

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References

REFERENCES

Venkataraman, D.; Yurt, S.; Venkatraman, B. H.; Gavvalapalli, , J. Phys. Chem. Lett. 1, 6 (2010).Google Scholar
Jiang, Y., et al. , Journal of Materials Chemistry. 22, 10 (2012).Google Scholar
Shirota, Y.; Kageyama, H., Chem. Rev. 107, 4 (2008).Google Scholar
Zaumseil, J.; Sirringhaus, H., Chem. Rev. 107, 4 (2007).Google Scholar
Bredas, J.-L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 104, 11 (2004).Google Scholar
Hummer, K.; Ambrosch-Draxl, C., Phys. Rev. B: Condens. Matter Mater. Phys. 72, 20 (2005)CrossRefGoogle Scholar
Zhou, Y., et al. , J. Am. Chem. Soc. 129, 41 (2007).Google Scholar
de Boer, R. W. I.; Klapwijk, T. M.; Morpurgo, A. F., Applied Physics Letters 83, 21 (2003).Google Scholar
Podzorov, V.; Pudalov, V. M.; Gershenson, M. E., Applied Physics Letters 82, 11 (2003).CrossRefGoogle Scholar
Mikolajczyk, M. M., et al. , J. Mol. Model. 17, 11 (2011).Google Scholar
Nenon, S., et al. , Thin Solid Films 518. 19 (2010).Google Scholar
Zeis, R.; Siegrist, T.; Kloc, C., Applied Physics Letters 86, 2 (2005).CrossRefGoogle Scholar
Irfan, A., et al. , Comput. Theor. Chem. 977,1–3 (2011).Google Scholar
Song, D., et al. , Applied Physics Letters 92, 14 (2008).Google Scholar
Rajesh, K. R., et al. , Bull. Mater. Sci. 37, 1 (2014).CrossRefGoogle Scholar
Bao, Z.; Lovinger, A. J.; Brown, J., J. Am. Chem. Soc. 120, 1 (1998).Google Scholar
Yoon, S. M, et al. Chem. Comm. 46 (2010).Google Scholar
Griswold, K.A. and Gorun, S.M., US Patent 20150266011Google Scholar
Gorun, S.M.; Sullivan, J.; and Ramji, K., US Patent 2015153888Google Scholar
Moons, H., et al. Inorg. Chem. 49 (2010).Google Scholar
Senevirathna, W.; Daddario, C. M.; Sauve, G., J. Phys. Chem. Lett. 5, 5 (2014).Google Scholar
Lin, T., et al. , Chem. Phys. 440, 47–52 (2014).Google Scholar
Schmidt, , et al. J. Comput. Chem. 14 (1993).Google Scholar
Becke, A. D. J. Chem. Phys. 98 (1993).Google Scholar
Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 109 (1998)Google Scholar
Dwyer, P. J., et al. , Journal of Physical Chemistry A 118 (2014).CrossRefGoogle Scholar