Synthesis and optoelectronic properties of benzoquinone-based donor-acceptor compounds
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Herein, we report a mild and efficient palladium-catalyzed C-H functionalization method to synthesize a series of benzoquinone-based charge transfer derivatives in good yields. The optoelectronic properties of these compounds were explored both theoretically and experimentally and correlations to structure were identified as a function of the nature and position of the donor group (meta and para) attached to the benzoquinone acceptor. Compound 3 , where benzoquinone is para-conjugated to the diphenylamine donor group, exhibited thermally activated delayed fluorescence (TADF) with a biexponential lifetime characterized by a prompt nanosecond component and a delayed component of 353 μs.
Sutherland , D , Sharma , N , Rosair , G , Samuel , I D W , Lee , A-L & Zysman-Colman , E 2019 , ' Synthesis and optoelectronic properties of benzoquinone-based donor-acceptor compounds ' , Beilstein Journal of Organic Chemistry , vol. 15 , pp. 2914-2921 . https://doi.org/10.3762/bjoc.15.285
Beilstein Journal of Organic Chemistry
Copyright © 2019 Sutherland et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
DescriptionWe thank Heriot-Watt University (James Watt Scholarship for DRS) for funding. Mass spectrometry data was acquired at the EPSRC UK National Mass Spectrometry Facility at Swansea University. We thank the Leverhulme Trust (RPG-2016-047) and EPSRC (EP/P010482/1) for financial support.
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