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Design and synthesis of novel p-type dopants for organic semiconductors

Electron transport in organic semiconductors can be controlled by doping with electron donors (n-type dopants) or acceptors (p-type dopants). One method of doping a semiconductor is to add a neutral molecule with an electron affinity higher than the ionization energy of the polymer. One of the most widely studied molecules for this purpose is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodi methane (F4TCNQ). However, F4TCNQ and related dopant molecules suffer from poor solubility in common solvents, which limits their applications.

   

We have recently devised a synthetic route to F4TCNQ analogues in which one or more of the cyano groups has been replaced with alkyl esters, leading to significantly increased solubility while maintaining electronic properties comparable to those of F4TCNQ. We are currently working on further modifications of F4TCNQ as well as the design of novel dopant molecules with the aid of ab initio calculations.

Lead references:

"Quantitative Measurements of the Temperature-dependent Microscopic and Macroscopic Dynamics of a Molecular Dopant in a Conjugated Polymer." Jun Li, Correy Koshnick, Souleymane O. Diallo, Sophia Ackling, David M. Huang, Ian E. Jacobs, Thomas Harrelson, Kunlun Hong, Guangwu Zhang, Joseph Beckett, Mark Mascal, and Adam J. Moule, Macromolecules 2017, 50, in press.

"Quantitative dedoping of conductive polymers." I. Jacobs, F. Wang, N. Hafezi, C. Medina-Plaza, T. Harrelson, J. Li, M. Augustine, M. Mascal, A. Moule, Chem. Mater. 2017, 29, 832.

"Comparison of solution-mixed and sequentially processed P3HT:F4TCNQ films: effect of doping-induced aggregation on film morphology." I. E. Jacobs, E. W. Aasen, J. L. Oliveira, T. N. Fonseca, J. D. Roehling, J. Li, G. Zhang, M. P. Augustine, M. Mascal, A. J. Moule, J. Mater. Chem. C 2016, 4, 3454.

"Introducing Solubility Control for Improved Organic p-type Dopants." J. Li, G. Zhang, D. Holm, I. E. Jacobs, B. Yin, P. Stroeve, M. Mascal, A. J. Moule, Chem. Mat., 2015, 27, 5765.

 

 

 

 

 

 

 

 

 

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