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.
Highlights
The discovery of the conductive properties of organic materials has led to the development of the large and expanding field of organic optoelectronics and conductive polymers, which encompasses technologies such as organic light-emitting diodes (OLED), organic photovoltaics (OPV) and dye sensitised solar cells (DSSC)
The synthesis of deuterated polyaromatic molecules for optoelectronic devices can be performed in a variety of ways, starting from either deuterated precursors that are assembled via standard organic chemistry techniques, or by performing hydrogen-deuterium exchange on the protonated molecule
The synthesis of three of the deuterated molecules we describe in this study (1, 2 and 3, Figure 2) has been previously reported, using Buchwald-Hartwig cross coupling of the respective deuterated amines and deuterated aryl halides
Summary
The discovery of the conductive properties of organic materials has led to the development of the large and expanding field of organic optoelectronics and conductive polymers, which encompasses technologies such as organic light-emitting diodes (OLED), organic photovoltaics (OPV) and dye sensitised solar cells (DSSC). In addition to their excellent electronic properties, the family of arylamines has favourable properties such as ion transfer processes, redox properties, and photoelectrochemical behaviour [1,2,3,4,5,6]. Polyaniline exists in three different oxidation states that have different properties
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