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Molecules 2014, 19(11), 18604-18617; doi:10.3390/molecules191118604

Mild Conditions for Deuteration of Primary and Secondary Arylamines for the Synthesis of Deuterated Optoelectronic Organic Molecules

National Deuteration Facility, Bragg Institute, Australian Nuclear Science and Technology Organisation (ANSTO), Locked Bag 2001, Kirrawee DC, NSW 2232, Australia
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Received: 5 September 2014 / Revised: 29 October 2014 / Accepted: 4 November 2014 / Published: 13 November 2014
(This article belongs to the Special Issue Deuterated Molecules and Polymers for Neutron Studies)
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Abstract

Deuterated arylamines demonstrate great potential for use in optoelectronic devices, but their widespread utility requires a method for large-scale synthesis. The incorporation of these deuterated materials into optoelectronic devices also provides the opportunity for studies of the functioning device using neutron reflectometry based on the difference in the scattering length density between protonated and deuterated compounds. Here we report mild deuteration conditions utilising standard laboratory glassware for the deuteration of: diphenylamine, N-phenylnaphthylamine, N-phenyl-o-phenylenediamine and 1-naphthylamine (via H/D exchange in D2O at 80 °C, catalysed by Pt/C and Pd/C). These conditions were not successful in the deuteration of triphenylamine or N,N-dimethylaniline, suggesting that these mild conditions are not suitable for the deuteration of tertiary arylamines, but are likely to be applicable for the deuteration of other primary and secondary arylamines. The deuterated arylamines can then be used for synthesis of larger organic molecules or polymers with optoelectronic applications. View Full-Text
Keywords: arylamine; deuteration; H/D exchange; neutron reflectrometry; OLED; optoelectronics arylamine; deuteration; H/D exchange; neutron reflectrometry; OLED; optoelectronics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Krause-Heuer, A.M.; Yepuri, N.R.; Darwish, T.A.; Holden, P.J. Mild Conditions for Deuteration of Primary and Secondary Arylamines for the Synthesis of Deuterated Optoelectronic Organic Molecules. Molecules 2014, 19, 18604-18617.

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