From phosphorescence to delayed fluorescence in one step: tuning photophysical properties by quaternisation of an sp2-hybridised nitrogen atom

Anastasia Klimash; Antonio Prlj; Dmitry S. Yufit; Abhijit Mallick; Basile F.E. Curchod; Paul R. McGonigal; Peter J. Skabara; Marc K. Etherington

doi:10.1039/d2tc01737g

From phosphorescence to delayed fluorescence in one step: tuning photophysical properties by quaternisation of an sp²-hybridised nitrogen atom

Anastasia Klimash, Antonio Prlj, Dmitry S. Yufit, Abhijit Mallick, Basile F.E. Curchod, Paul R. McGonigal, Peter J. Skabara^*, Marc K. Etherington

^*Corresponding author for this work

Chemistry

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

Abstract

Control of the delayed emission of organic compounds is an important factor in the development of new display technology and for the emerging use of organic emitters in sensing and fluorescence microscopy. In particular, there is a need to understand how the phenomena of room-temperature phosphorescence and thermally activated delayed fluorescence intersect. Here, we show that delayed fluorescence can be activated in room temperature phosphorescence emitters by quaternising the sp²-hybridised heterocyclic nitrogens. Furthermore by judicious positioning of a carbazole donor in the meta- or para-position with respect to the ring nitrogen atom, structural and sterical influences combine to tune the origins of the delayed fluorescence from triplet-triplet annihilation to thermally activated delayed fluorescence. Crucially, the quaternisation of nitrogen provides us with the means to fine-tune singlet and triplet states in a predictable manner, uncover the intersection between phosphorescence and delayed fluorescence and tip the balance in favour of delayed fluorescence.

Original language	English
Pages (from-to)	9484-9491
Number of pages	8
Journal	Journal of Materials Chemistry C
Volume	10
Issue number	25
DOIs	https://doi.org/10.1039/d2tc01737g
Publication status	Published - 25 May 2022

Bibliographical note

Funding Information:
This research has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement H2020-MSCA-ITN2015/674990 project ‘‘EXCILIGHT’’. A. K. also thanks the EPSRC for funding (EP/T013710/1). M. K. E. thanks the Royal Society of Chemistry (R20-1668) for support. The authors also thank Andrew P. Monkman for use of his facilities for the spectroscopic work.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

Access to Document

10.1039/d2tc01737gLicence: CC BY

From phosphorescence to delayed fluorescence in one step: tuning photophysical properties by quaternisation of an sp2-hybridised nitrogen atom
© The Royal Society of Chemistry 2022
Final published version, 4.64 MBLicence: CC BY

Cite this

@article{d3ad5b51af8f4145beec5b30f6d08959,

title = "From phosphorescence to delayed fluorescence in one step: tuning photophysical properties by quaternisation of an sp2-hybridised nitrogen atom",

abstract = "Control of the delayed emission of organic compounds is an important factor in the development of new display technology and for the emerging use of organic emitters in sensing and fluorescence microscopy. In particular, there is a need to understand how the phenomena of room-temperature phosphorescence and thermally activated delayed fluorescence intersect. Here, we show that delayed fluorescence can be activated in room temperature phosphorescence emitters by quaternising the sp2-hybridised heterocyclic nitrogens. Furthermore by judicious positioning of a carbazole donor in the meta- or para-position with respect to the ring nitrogen atom, structural and sterical influences combine to tune the origins of the delayed fluorescence from triplet-triplet annihilation to thermally activated delayed fluorescence. Crucially, the quaternisation of nitrogen provides us with the means to fine-tune singlet and triplet states in a predictable manner, uncover the intersection between phosphorescence and delayed fluorescence and tip the balance in favour of delayed fluorescence.",

author = "Anastasia Klimash and Antonio Prlj and Yufit, {Dmitry S.} and Abhijit Mallick and Curchod, {Basile F.E.} and McGonigal, {Paul R.} and Skabara, {Peter J.} and Etherington, {Marc K.}",

note = "Funding Information: This research has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Sk{\l}odowska-Curie grant agreement H2020-MSCA-ITN2015/674990 project {\textquoteleft}{\textquoteleft}EXCILIGHT{\textquoteright}{\textquoteright}. A. K. also thanks the EPSRC for funding (EP/T013710/1). M. K. E. thanks the Royal Society of Chemistry (R20-1668) for support. The authors also thank Andrew P. Monkman for use of his facilities for the spectroscopic work. Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = may,

day = "25",

doi = "10.1039/d2tc01737g",

language = "English",

volume = "10",

pages = "9484--9491",

journal = "Journal of Materials Chemistry C",

issn = "2050-7526",

publisher = "The Royal Society of Chemistry",

number = "25",

}

TY - JOUR

T1 - From phosphorescence to delayed fluorescence in one step

T2 - tuning photophysical properties by quaternisation of an sp2-hybridised nitrogen atom

AU - Klimash, Anastasia

AU - Prlj, Antonio

AU - Yufit, Dmitry S.

AU - Mallick, Abhijit

AU - Curchod, Basile F.E.

AU - McGonigal, Paul R.

AU - Skabara, Peter J.

AU - Etherington, Marc K.

N1 - Funding Information: This research has received funding from the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement H2020-MSCA-ITN2015/674990 project ‘‘EXCILIGHT’’. A. K. also thanks the EPSRC for funding (EP/T013710/1). M. K. E. thanks the Royal Society of Chemistry (R20-1668) for support. The authors also thank Andrew P. Monkman for use of his facilities for the spectroscopic work. Publisher Copyright: © 2022 The Royal Society of Chemistry.

PY - 2022/5/25

Y1 - 2022/5/25

N2 - Control of the delayed emission of organic compounds is an important factor in the development of new display technology and for the emerging use of organic emitters in sensing and fluorescence microscopy. In particular, there is a need to understand how the phenomena of room-temperature phosphorescence and thermally activated delayed fluorescence intersect. Here, we show that delayed fluorescence can be activated in room temperature phosphorescence emitters by quaternising the sp2-hybridised heterocyclic nitrogens. Furthermore by judicious positioning of a carbazole donor in the meta- or para-position with respect to the ring nitrogen atom, structural and sterical influences combine to tune the origins of the delayed fluorescence from triplet-triplet annihilation to thermally activated delayed fluorescence. Crucially, the quaternisation of nitrogen provides us with the means to fine-tune singlet and triplet states in a predictable manner, uncover the intersection between phosphorescence and delayed fluorescence and tip the balance in favour of delayed fluorescence.

AB - Control of the delayed emission of organic compounds is an important factor in the development of new display technology and for the emerging use of organic emitters in sensing and fluorescence microscopy. In particular, there is a need to understand how the phenomena of room-temperature phosphorescence and thermally activated delayed fluorescence intersect. Here, we show that delayed fluorescence can be activated in room temperature phosphorescence emitters by quaternising the sp2-hybridised heterocyclic nitrogens. Furthermore by judicious positioning of a carbazole donor in the meta- or para-position with respect to the ring nitrogen atom, structural and sterical influences combine to tune the origins of the delayed fluorescence from triplet-triplet annihilation to thermally activated delayed fluorescence. Crucially, the quaternisation of nitrogen provides us with the means to fine-tune singlet and triplet states in a predictable manner, uncover the intersection between phosphorescence and delayed fluorescence and tip the balance in favour of delayed fluorescence.

UR - http://www.scopus.com/inward/record.url?scp=85131817812&partnerID=8YFLogxK

U2 - 10.1039/d2tc01737g

DO - 10.1039/d2tc01737g

M3 - Article

AN - SCOPUS:85131817812

SN - 2050-7526

VL - 10

SP - 9484

EP - 9491

JO - Journal of Materials Chemistry C

JF - Journal of Materials Chemistry C

IS - 25

ER -