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

doi:10.3762/bjoc.15.285

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

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Abstract

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 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

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10.3762/bjoc.15.285Licence: CC BY

Sutherland_2019_BJOC_Benzoquinone_CC
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.
Final published version, 1.43 MBLicence: CC BY

TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs
Zysman-Colman, E. (PI)
EPSRC
1/03/17 → 31/03/21
Project: Standard
Blue-Emitting TADF Materials: Blue-Emitting TADF Materials for OLEDs Based on a Lewis Acid-Containing Acceptor
Zysman-Colman, E. (PI)
The Leverhulme Trust
1/08/16 → 30/04/22
Project: Standard

Synthesis and Optoelectronic Properties of Benzoquinone-Based Donor- Acceptor Compounds (dataset)
Sutherland, D. R. (Creator), Sharma, N. (Creator), Rosair, G. M. (Creator), Samuel, I. D. W. (Creator), Lee, A.-L. (Creator) & Zysman-Colman, E. (Creator), University of St Andrews, 2019
DOI: 10.17630/178f3a7c-4717-43f0-a145-049675825e1a
Dataset

File

Cite this

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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-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.",

keywords = "Materials chemistry, Physical organic chemistry, Spectroscopy, Thermally activated delayed fluorescence",

author = "Daniel Sutherland and Nidhi Sharma and Georgina Rosair and Samuel, {Ifor D. W.} and Ai-Lan Lee and Eli Zysman-Colman",

note = "We 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.",

year = "2019",

month = dec,

day = "4",

doi = "10.3762/bjoc.15.285",

language = "English",

volume = "15",

pages = "2914--2921",

journal = "Beilstein Journal of Organic Chemistry",

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publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - Synthesis and optoelectronic properties of benzoquinone-based donor-acceptor compounds

AU - Sutherland, Daniel

AU - Sharma, Nidhi

AU - Rosair, Georgina

AU - Samuel, Ifor D. W.

AU - Lee, Ai-Lan

AU - Zysman-Colman, Eli

N1 - We 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.

PY - 2019/12/4

Y1 - 2019/12/4

N2 - 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.

AB - 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.

KW - Materials chemistry

KW - Physical organic chemistry

KW - Spectroscopy

KW - Thermally activated delayed fluorescence

U2 - 10.3762/bjoc.15.285

DO - 10.3762/bjoc.15.285

M3 - Article

SN - 1860-5397

VL - 15

SP - 2914

EP - 2921

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Keywords

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Projects

TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs

Blue-Emitting TADF Materials: Blue-Emitting TADF Materials for OLEDs Based on a Lewis Acid-Containing Acceptor

Datasets

Synthesis and Optoelectronic Properties of Benzoquinone-Based Donor- Acceptor Compounds (dataset)

Cite this