Synthesis and optoelectronic properties of benzoquinone-based donor-acceptor compounds

Daniel Sutherland, Nidhi Sharma, Georgina Rosair, Ifor D. W. Samuel, Ai-Lan Lee, Eli Zysman-Colman

Research output: Contribution to journalArticlepeer-review


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.
Original languageEnglish
Pages (from-to)2914-2921
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Publication statusPublished - 4 Dec 2019


  • Materials chemistry
  • Physical organic chemistry
  • Spectroscopy
  • Thermally activated delayed fluorescence


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