Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters

Kang Yuan; Abhishek Kumar Gupta; Changfeng Si; Marina Uzelac; Eli Zysman-Colman; Michael James Ingleson

doi:10.1021/acs.orglett.3c02167

Brominated B₁-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters

Kang Yuan, Abhishek Kumar Gupta, Changfeng Si, Marina Uzelac, Eli Zysman-Colman^*, Michael James Ingleson^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

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Abstract

Bromo-functionalized B1-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than −3.0 eV were synthesized and used in cross-couplings to form donor–acceptor materials. These materials spanned a range of S1 energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B1-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized.

Original language	English
Pages (from-to)	5880-5884
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	31
Early online date	27 Jul 2023
DOIs	https://doi.org/10.1021/acs.orglett.3c02167
Publication status	Published - 11 Aug 2023

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10.1021/acs.orglett.3c02167Licence: CC BY

Yuan_2023_OL_Brominated-B1-polycyclic_CC
Copyright © 2023 The Authors. Published by American Chemical Society under under a Creative Commons CC BY licence.
Final published version, 2.36 MBLicence: CC BY

Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. J. B. (PI), Morris, R. E. (CoI), Smith, A. D. (CoI) & Zysman-Colman, E. (CoI)
UK Research and Innovation
1/05/23 → 30/04/28
Project: Standard
Going Deeper with Boron: Near-infrared emitting TADF materials based on very strong organoboron acceptors
Zysman-Colman, E. (PI)
The Leverhulme Trust
1/07/22 → 31/08/26
Project: Standard

Brominated B1-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-IR Delayed Fluorescence Emitters (dataset)
Yuana, K. (Creator), Gupta, A. K. (Creator), Si, C. (Creator), Uzelac, M. (Creator), Zysman-Colman, E. (Creator) & Ingleson, M. J. (Creator), University of St Andrews, 13 Sept 2023
DOI: 10.17630/fd1c4863-0606-4595-9c89-f40ef45fef4d
Dataset

File
Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters (dataset)
Yuan, K. (Creator), Gupta, A. K. (Creator), Si, C. (Creator), Uzelac, M. (Creator), Zysman-Colman, E. (Creator) & Ingleson, M. J. (Creator), Cambridge Crystallographic Data Centre, 2023
https://dx.doi.org/10.5517/ccdc.csd.cc2g1t8m and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc2g1t7l (show fewer)
Dataset

Cite this

@article{5301cb8ea45c4312b28a6870a436f81b,

title = "Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters",

abstract = "Bromo-functionalized B1-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than −3.0 eV were synthesized and used in cross-couplings to form donor–acceptor materials. These materials spanned a range of S1 energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B1-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized.",

author = "Kang Yuan and Gupta, {Abhishek Kumar} and Changfeng Si and Marina Uzelac and Eli Zysman-Colman and Ingleson, {Michael James}",

note = "Funding: This project has received funding from the Leverhulme Trust (Grant RPG-2022-032) and the European Research Council (ERC) under the European Union{\textquoteright}s Horizon 2020 research and innovation program (Grant Agreement 769599). C.S. thanks the China Scholarship Council (201806890001), and M.I. and E.Z.-C. thank the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517) for support.",

year = "2023",

month = aug,

day = "11",

doi = "10.1021/acs.orglett.3c02167",

language = "English",

volume = "25",

pages = "5880--5884",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "31",

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TY - JOUR

T1 - Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters

AU - Yuan, Kang

AU - Gupta, Abhishek Kumar

AU - Si, Changfeng

AU - Uzelac, Marina

AU - Zysman-Colman, Eli

AU - Ingleson, Michael James

N1 - Funding: This project has received funding from the Leverhulme Trust (Grant RPG-2022-032) and the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation program (Grant Agreement 769599). C.S. thanks the China Scholarship Council (201806890001), and M.I. and E.Z.-C. thank the EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517) for support.

PY - 2023/8/11

Y1 - 2023/8/11

N2 - Bromo-functionalized B1-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than −3.0 eV were synthesized and used in cross-couplings to form donor–acceptor materials. These materials spanned a range of S1 energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B1-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized.

AB - Bromo-functionalized B1-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than −3.0 eV were synthesized and used in cross-couplings to form donor–acceptor materials. These materials spanned a range of S1 energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B1-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized.

U2 - 10.1021/acs.orglett.3c02167

DO - 10.1021/acs.orglett.3c02167

M3 - Article

SN - 1523-7060

VL - 25

SP - 5880

EP - 5884

JO - Organic Letters

JF - Organic Letters

IS - 31

ER -

Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters

Abstract

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Projects

Allan Watson Programme Grant: Boron: Beyond the Reagent

Going Deeper with Boron: Near-infrared emitting TADF materials based on very strong organoboron acceptors

Datasets

Brominated B1-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-IR Delayed Fluorescence Emitters (dataset)

Brominated B1-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters (dataset)

Cite this

Brominated B₁-polycyclic aromatic hydrocarbons for the synthesis of deep-red to near-infrared delayed fluorescence emitters