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

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

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Abstract

Herein, we report a mild and efficient palladium-catalyzed C–H functionalization method to synthesize a series of benzoquinone (BQ)-based charge-transfer (CT) derivatives in good yields. The optoelectronic properties of these compounds were explored both theoretically and experimentally and correlations to their structures 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 ns component and a delayed component of 353 μs.

Original languageEnglish
Pages (from-to)2914-2921
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 4 Dec 2019

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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