Donor influence on the optoelectronic properties of N-substituted tetraphenylimidazole derivatives

Tomas Matulaitis; Paloma L dos Santos; Youichi Tsuchiya; David B. Cordes; Alexandra M. Z. Slawin; Chihaya Adachi; Ifor D. W. Samuel; Eli Zysman-Colman

doi:10.1002/slct.202300274

Donor influence on the optoelectronic properties of N-substituted tetraphenylimidazole derivatives

Tomas Matulaitis, Paloma L dos Santos, Youichi Tsuchiya, David B. Cordes, Alexandra M. Z. Slawin, Chihaya Adachi, Ifor D. W. Samuel^*, Eli Zysman-Colman^*

^*Corresponding author for this work

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

Abstract

Three new 1,2,4,5-tetraphenylimidazole derivatives, 9,9-dimethyl-10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-9,10-dihydroacridine (DMAC-TPI), 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenoxazine (PXZ-TPI), and 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenothiazine (PTZ-TPI), bearing different electron donors at the N1 position of the imidazole were synthesised and characterised. DMAC-TPI and PXZ-TPI showed narrow emission at λ_PL of 388 and 418 nm in toluene, and in doped films in Zeonex polymer (1 wt.%) at λ_PL 381 and 407 nm, respectively, with a full width at half maximum (FWHM) ranging 0.42-0.44 eV. DMAC-TPI and PXZ-TPI are predicted to show very low oscillator strength for the low-energy transitions, which aligns to the observed low photoluminescence quantum yields. Both molecules showed a singlet-triplet energy gap (ΔE_ST of around 1.2 eV) that is much too large to enable reverse intersystem crossing and thermally activated delayed fluorescence. Connecting a donor group to TPI at the N1 position can lead to room temperature phosphorescence (RTP), as the example of PTZ-TPI showed.

Original language	English
Article number	e202300274
Number of pages	10
Journal	ChemistrySelect
Volume	8
Issue number	9
Early online date	28 Feb 2023
DOIs	https://doi.org/10.1002/slct.202300274
Publication status	Published - 6 Mar 2023

Keywords

Bipolar
Charge transfer
DFT
Photophysics
Weak acceptor

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Matulaitis_2023_CS_Donorinfluence_CC
Copyright © 2023 The Authors. ChemistrySelect published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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EPSRC-JSPS Core-to-core Grant: EPSRC-JSPS Core-to-Core Grant Application
Samuel, I. D. W. (PI)
1/08/18 → 31/07/23
Project: Standard
Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application
Zysman-Colman, E. (PI)
1/08/18 → 31/01/24
Project: Standard
TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs
Zysman-Colman, E. (PI)
EPSRC
1/03/17 → 31/03/21
Project: Standard

Donor Influence on the Optoelectronic Properties of N-Substituted Tetraphenylimidazole Derivatives (dataset)
Matulaitis, T. (Creator), dos Santos, P. L. (Creator), Tsuchiya, Y. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Adachi, C. (Creator), Samuel, I. D. W. (Creator) & Zysman-Colman, E. (Creator), University of St Andrews, 8 Jun 2023
DOI: 10.17630/2a75f75c-f023-4c2b-a06d-5ed67454c81b
Dataset

File

Cite this

@article{3e451fc215f54e41ab68c00e6637bbbf,

title = "Donor influence on the optoelectronic properties of N-substituted tetraphenylimidazole derivatives",

abstract = "Three new 1,2,4,5-tetraphenylimidazole derivatives, 9,9-dimethyl-10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-9,10-dihydroacridine (DMAC-TPI), 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenoxazine (PXZ-TPI), and 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenothiazine (PTZ-TPI), bearing different electron donors at the N1 position of the imidazole were synthesised and characterised. DMAC-TPI and PXZ-TPI showed narrow emission at λPL of 388 and 418 nm in toluene, and in doped films in Zeonex polymer (1 wt.%) at λPL 381 and 407 nm, respectively, with a full width at half maximum (FWHM) ranging 0.42-0.44 eV. DMAC-TPI and PXZ-TPI are predicted to show very low oscillator strength for the low-energy transitions, which aligns to the observed low photoluminescence quantum yields. Both molecules showed a singlet-triplet energy gap (ΔEST of around 1.2 eV) that is much too large to enable reverse intersystem crossing and thermally activated delayed fluorescence. Connecting a donor group to TPI at the N1 position can lead to room temperature phosphorescence (RTP), as the example of PTZ-TPI showed.",

keywords = "Bipolar, Charge transfer, DFT, Photophysics, Weak acceptor",

author = "Tomas Matulaitis and {dos Santos}, {Paloma L} and Youichi Tsuchiya and Cordes, {David B.} and Slawin, {Alexandra M. Z.} and Chihaya Adachi and Samuel, {Ifor D. W.} and Eli Zysman-Colman",

note = "Funding: The St Andrews team is grateful to the Engineering and Physical Sciences Research Council (EPSRC) for support from grants EP/P010482/1, EP/R035164/1 and EP/L017008/1. Kyushu team would like to acknowledge Kyulux inc and JSPS Core-to-Core Program (grant number: JPJSCCA20180005) for the support of this project.",

year = "2023",

month = mar,

day = "6",

doi = "10.1002/slct.202300274",

language = "English",

volume = "8",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley",

number = "9",

}

TY - JOUR

T1 - Donor influence on the optoelectronic properties of N-substituted tetraphenylimidazole derivatives

AU - Matulaitis, Tomas

AU - dos Santos, Paloma L

AU - Tsuchiya, Youichi

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Adachi, Chihaya

AU - Samuel, Ifor D. W.

AU - Zysman-Colman, Eli

N1 - Funding: The St Andrews team is grateful to the Engineering and Physical Sciences Research Council (EPSRC) for support from grants EP/P010482/1, EP/R035164/1 and EP/L017008/1. Kyushu team would like to acknowledge Kyulux inc and JSPS Core-to-Core Program (grant number: JPJSCCA20180005) for the support of this project.

PY - 2023/3/6

Y1 - 2023/3/6

N2 - Three new 1,2,4,5-tetraphenylimidazole derivatives, 9,9-dimethyl-10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-9,10-dihydroacridine (DMAC-TPI), 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenoxazine (PXZ-TPI), and 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenothiazine (PTZ-TPI), bearing different electron donors at the N1 position of the imidazole were synthesised and characterised. DMAC-TPI and PXZ-TPI showed narrow emission at λPL of 388 and 418 nm in toluene, and in doped films in Zeonex polymer (1 wt.%) at λPL 381 and 407 nm, respectively, with a full width at half maximum (FWHM) ranging 0.42-0.44 eV. DMAC-TPI and PXZ-TPI are predicted to show very low oscillator strength for the low-energy transitions, which aligns to the observed low photoluminescence quantum yields. Both molecules showed a singlet-triplet energy gap (ΔEST of around 1.2 eV) that is much too large to enable reverse intersystem crossing and thermally activated delayed fluorescence. Connecting a donor group to TPI at the N1 position can lead to room temperature phosphorescence (RTP), as the example of PTZ-TPI showed.

AB - Three new 1,2,4,5-tetraphenylimidazole derivatives, 9,9-dimethyl-10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-9,10-dihydroacridine (DMAC-TPI), 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenoxazine (PXZ-TPI), and 10-(4-(2,4,5-triphenyl-1H-imidazol-1-yl)phenyl)-10H-phenothiazine (PTZ-TPI), bearing different electron donors at the N1 position of the imidazole were synthesised and characterised. DMAC-TPI and PXZ-TPI showed narrow emission at λPL of 388 and 418 nm in toluene, and in doped films in Zeonex polymer (1 wt.%) at λPL 381 and 407 nm, respectively, with a full width at half maximum (FWHM) ranging 0.42-0.44 eV. DMAC-TPI and PXZ-TPI are predicted to show very low oscillator strength for the low-energy transitions, which aligns to the observed low photoluminescence quantum yields. Both molecules showed a singlet-triplet energy gap (ΔEST of around 1.2 eV) that is much too large to enable reverse intersystem crossing and thermally activated delayed fluorescence. Connecting a donor group to TPI at the N1 position can lead to room temperature phosphorescence (RTP), as the example of PTZ-TPI showed.

KW - Bipolar

KW - Charge transfer

KW - DFT

KW - Photophysics

KW - Weak acceptor

U2 - 10.1002/slct.202300274

DO - 10.1002/slct.202300274

M3 - Article

SN - 2365-6549

VL - 8

JO - ChemistrySelect

JF - ChemistrySelect

IS - 9

M1 - e202300274

ER -

Donor influence on the optoelectronic properties of N-substituted tetraphenylimidazole derivatives

Abstract

Keywords

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Projects

EPSRC-JSPS Core-to-core Grant: EPSRC-JSPS Core-to-Core Grant Application

Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application

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

Datasets

Donor Influence on the Optoelectronic Properties of N-Substituted Tetraphenylimidazole Derivatives (dataset)

Cite this