The organic optoelectronics materials such as conducting polymers are widely used in organic light-emitting diodes (OLED), organic photovoltaics (OPV) and dye sensitised solar cells (DSSC) and others. Today, there is much interest in the development of new optoelectronics materials with specific/tunable and desirable photoelectric properties. For example, effort has been focused on improving the low electricity-to-light conversion efficiency, as well as the poor high-voltage stability of OLED optoelectronics materials. It has been recently reported that selective deuteration of conducting polymers significantly alters the optoelectronic properties and magnetic responses of the molecules. As such, there is particular interest in deuterated molecular for use in optoelectronic materials, and the synthesis of deuterated molecular for optoelectronic materials are highly dependent on some basic deuterium reagents.
Why does deuterium affect optoelectronic material properties?
Due to the large relative mass difference of deuterium and hydrogen, the physical properties such as polarity, polarizability and molecular volume of the protonated and deuterated polymers could be different. These factors could in principle lead to a change of non-covalent (for example, hydrogen bonding, CH-π, π-π, and cation-π) interactions upon deuteration, which has an effect on the optoelectronic properties of conducting polymers .
Application of deuterated reagents in optoelectronic materials
Researches showed that the optoelectronic properties and other properties of materials can be significantly improved by using deuterated molecules to synthesize optoelectronic materials. In general, deuterated molecules used in optoelectronic materials require deuterated reagents as raw materials for synthesis. The synthesis of deuterated molecules by deuterated reagents can be performed in a variety of ways, starting from either deuterated precursors that are assembled via organic chemistry techniques, or by performing hydrogen-deuterium exchange by D2O, D2 or deuterated protic solvents to provide labile deuterium atoms.
For examples, Krause-Heuer et al . synthesized the deuterated arylamines molecules for optoelectronic materials by using Buchwald-Hartwig cross coupling of the respective deuterated amines (d5-aniline) and deuterated aryl halides (d5-bromobenzene), as shown in Fig. 1.
Fig. 1 The synthesis of deuterated arylamines molecules via the Buchwald-Hartwig cross coupling of d5-bromobenzene and d5-aniline.
Alternatively, the authors synthesized deuterated arylamines molecules also using H/D exchange with D2O as deuterium source. The experiment was facilitated by a combination of Pd/C (~1 mol %) and Pt/C (~1.5 mol %), with the reaction mixture purged with N2 (g) and then H2 (g) prior to heating at 80 ℃ for 4-24 h, as shown in Fig. 2. These deuterated arylamines are incorporated into optoelectronic materials, which may have better lifetime and efficiency compared to the protonated version, 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.
Fig. 2 The synthesis of four kinds of deuterated arylamines molecules via H/D exchange in D2O, catalyzed by Pt/C and Pd/C.
What can we do?
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- Shao, M., et al. The isotopic effects of deuteration on optoelectronic properties of conducting polymers[J]. Nature communications, 2014, 5(1): 1-11.
- Krause-Heuer, A. M., et al. Mild conditions for deuteration of primary and secondary arylamines for the synthesis of deuterated optoelectronic organic molecules[J]. Molecules, 2014, 19(11): 18604-18617.
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