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

doi:10.3762/bjoc.15.285

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 language	English
Pages (from-to)	2914-2921
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.285
Publication status	Published - 4 Dec 2019

Keywords

Materials chemistry
Physical organic chemistry
Spectroscopy
Thermally activated delayed fluorescence

ASJC Scopus subject areas

Organic Chemistry

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title = "Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds",

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.",

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AU - Sutherland, Daniel R.

AU - Sharma, Nidhi

AU - Rosair, Georgina M.

AU - Samuel, Ifor D. W.

AU - Lee, Ai-Lan

AU - Zysman-Colman, Eli

PY - 2019/12/4

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N2 - 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.

AB - 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.

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KW - Physical organic chemistry

KW - Spectroscopy

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JO - Beilstein Journal of Organic Chemistry

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

Abstract

Keywords

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