A novel carbazolophane: a comparison of the performance of two planar chiral CP-TADF emitters

Jasmin Seibert; Yan Xu; Hassan Hafeez; Joachim Podlech; Ludovic Favereau; Eduard Spuling; Charlotte Waldhelm; Martin Nieger; Olaf Fuhr; Zahid Hassan; Jeanne Crassous; Ifor D. W. Samuel; Eli Zysman-Colman; Stefan Bräse

doi:10.1002/adfm.202401956

A novel carbazolophane: a comparison of the performance of two planar chiral CP-TADF emitters

Jasmin Seibert, Yan Xu, Hassan Hafeez, Joachim Podlech, Ludovic Favereau, Eduard Spuling, Charlotte Waldhelm, Martin Nieger, Olaf Fuhr, Zahid Hassan, Jeanne Crassous, Ifor D. W. Samuel^*, Eli Zysman-Colman^*, Stefan Bräse^*

^*Corresponding author for this work

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

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Abstract

The prototypical example of a (cyclo)phane, [2.2]paracyclophane (PCP), has proven to be a versatile stereogenic moiety within the design of circularly polarized thermally activated delayed fluorescence (CP-TADF) emitters; however, the exploration of other cyclophanes within CP-TADF emitter design has been largely neglected. Here, a comparative study of the photophysical and optoelectronic properties of two cyclophane emitters, (1,7)tBuCzpPhTrz and its isomer (1,4)tBuCzpPhTrz, is presented. The carbazolophane-triazine compound (1,7)tBuCzpPhTrz, obtained via an unprecedented intramolecular rearrangement, is the first example of a planar chiral TADF emitter deviating from the PCP scaffold. Significant geometrical change of the enclosed carbazole in (1,7)tBuCzp results in an attenuation of the donor strength, while the merits of rigidity and steric bulk remain. In particular, the full width at half maximum (FWHM) of the photoluminescence spectrum in toluene of (1,7)tBuCzpPhTrz is reduced by 34% and blue-shifted by 20 nm compared to that of (1,4)tBuCzpPhTrz. In doped films, the compounds reach high photoluminescence quantum yields (ΦPL) of 91 and 81%, respectively. The chiroptical properties reveal dissymmetry factors |gPL| of up to 5 ? 10?4. These results demonstrate the impact of the cyclophane for the development of CP-TADF materials and add to the currently limited scope of available planar chiral donors.

Original language	English
Number of pages	13
Journal	Advanced Functional Materials
Volume	EarlyView
Early online date	25 Apr 2024
DOIs	https://doi.org/10.1002/adfm.202401956
Publication status	E-pub ahead of print - 25 Apr 2024

Keywords

Carbazolophanes
Circularly polarized luminescence
Cyclophanes
Organic light-emitting diodes
Planar chirality
Thermally activated delayed fluorescence

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Seibert_2024_AFM_Novel-carbazolophane_CC
Copyright © 2024 The Authors. Advanced Functional Materials 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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MR TADF: Multi-resonance TADF materials for highly efficient and stable OLEDs
Samuel, I. D. W. (PI)
EPSRC
1/07/22 → 30/06/25
Project: Standard
MR TADF: Multi-resonance TADF materials for highly efficient and stable OLEDs
Zysman-Colman, E. (PI)
EPSRC
1/07/22 → 30/06/25
Project: Standard
Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application
Zysman-Colman, E. (PI)
1/08/18 → 31/01/24
Project: Standard

A Novel Carbazolophane: A Comparison of the Performance of Two Planar Chiral CPTADF Emitters (dataset)
Seibert, J. (Creator), Xu, Y. (Creator), Hafeez, H. (Creator), Podlech, J. (Creator), Favereau, L. (Creator), Spuling, E. (Creator), Waldhelm, C. (Creator), Nieger, M. (Creator), Fuhr, O. (Creator), Hassan, Z. (Creator), Crassous, J. (Creator), Samuel, I. D. W. (Creator), Zysman-Colman, E. (Creator) & Bräse, S. (Creator), University of St Andrews, 3 May 2024
DOI: 10.17630/ceaea778-414a-4ef9-adf7-bdf228a42080
Dataset

File

Cite this

Seibert, J., Xu, Y., Hafeez, H., Podlech, J., Favereau, L., Spuling, E., Waldhelm, C., Nieger, M., Fuhr, O., Hassan, Z., Crassous, J., Samuel, I. D. W., Zysman-Colman, E., & Bräse, S. (2024). A novel carbazolophane: a comparison of the performance of two planar chiral CP-TADF emitters. Advanced Functional Materials, EarlyView. Advance online publication. https://doi.org/10.1002/adfm.202401956

@article{35cb63cb6938402fb36325f5be05268e,

title = "A novel carbazolophane: a comparison of the performance of two planar chiral CP-TADF emitters",

abstract = "The prototypical example of a (cyclo)phane, [2.2]paracyclophane (PCP), has proven to be a versatile stereogenic moiety within the design of circularly polarized thermally activated delayed fluorescence (CP-TADF) emitters; however, the exploration of other cyclophanes within CP-TADF emitter design has been largely neglected. Here, a comparative study of the photophysical and optoelectronic properties of two cyclophane emitters, (1,7)tBuCzpPhTrz and its isomer (1,4)tBuCzpPhTrz, is presented. The carbazolophane-triazine compound (1,7)tBuCzpPhTrz, obtained via an unprecedented intramolecular rearrangement, is the first example of a planar chiral TADF emitter deviating from the PCP scaffold. Significant geometrical change of the enclosed carbazole in (1,7)tBuCzp results in an attenuation of the donor strength, while the merits of rigidity and steric bulk remain. In particular, the full width at half maximum (FWHM) of the photoluminescence spectrum in toluene of (1,7)tBuCzpPhTrz is reduced by 34% and blue-shifted by 20 nm compared to that of (1,4)tBuCzpPhTrz. In doped films, the compounds reach high photoluminescence quantum yields (ΦPL) of 91 and 81%, respectively. The chiroptical properties reveal dissymmetry factors |gPL| of up to 5 ? 10?4. These results demonstrate the impact of the cyclophane for the development of CP-TADF materials and add to the currently limited scope of available planar chiral donors.",

keywords = "Carbazolophanes, Circularly polarized luminescence, Cyclophanes, Organic light-emitting diodes, Planar chirality, Thermally activated delayed fluorescence",

author = "Jasmin Seibert and Yan Xu and Hassan Hafeez and Joachim Podlech and Ludovic Favereau and Eduard Spuling and Charlotte Waldhelm and Martin Nieger and Olaf Fuhr and Zahid Hassan and Jeanne Crassous and Samuel, {Ifor D. W.} and Eli Zysman-Colman and Stefan Br{\"a}se",

note = "J{\"u}rgen Manchot Foundation Deutsche Forschungsgemeinschaft. Grant Number: EXC-2082/1–390761711 China Scholarship Council. Grant Number: 202106310038 Engineering and Physical Sciences Research Council. Grant Numbers: EP/R035164/1, EP/W015137/1, EP/W524505/1 Helmholtz Association Program Minist{\`e}re de l{\textquoteright}Enseignement Sup{\'e}rieur et de la Recherche Centre National de la Recherche Scientifique",

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doi = "10.1002/adfm.202401956",

language = "English",

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T1 - A novel carbazolophane

T2 - a comparison of the performance of two planar chiral CP-TADF emitters

AU - Seibert, Jasmin

AU - Xu, Yan

AU - Hafeez, Hassan

AU - Podlech, Joachim

AU - Favereau, Ludovic

AU - Spuling, Eduard

AU - Waldhelm, Charlotte

AU - Nieger, Martin

AU - Fuhr, Olaf

AU - Hassan, Zahid

AU - Crassous, Jeanne

AU - Samuel, Ifor D. W.

AU - Zysman-Colman, Eli

AU - Bräse, Stefan

N1 - Jürgen Manchot Foundation Deutsche Forschungsgemeinschaft. Grant Number: EXC-2082/1–390761711 China Scholarship Council. Grant Number: 202106310038 Engineering and Physical Sciences Research Council. Grant Numbers: EP/R035164/1, EP/W015137/1, EP/W524505/1 Helmholtz Association Program Ministère de l’Enseignement Supérieur et de la Recherche Centre National de la Recherche Scientifique

PY - 2024/4/25

Y1 - 2024/4/25

N2 - The prototypical example of a (cyclo)phane, [2.2]paracyclophane (PCP), has proven to be a versatile stereogenic moiety within the design of circularly polarized thermally activated delayed fluorescence (CP-TADF) emitters; however, the exploration of other cyclophanes within CP-TADF emitter design has been largely neglected. Here, a comparative study of the photophysical and optoelectronic properties of two cyclophane emitters, (1,7)tBuCzpPhTrz and its isomer (1,4)tBuCzpPhTrz, is presented. The carbazolophane-triazine compound (1,7)tBuCzpPhTrz, obtained via an unprecedented intramolecular rearrangement, is the first example of a planar chiral TADF emitter deviating from the PCP scaffold. Significant geometrical change of the enclosed carbazole in (1,7)tBuCzp results in an attenuation of the donor strength, while the merits of rigidity and steric bulk remain. In particular, the full width at half maximum (FWHM) of the photoluminescence spectrum in toluene of (1,7)tBuCzpPhTrz is reduced by 34% and blue-shifted by 20 nm compared to that of (1,4)tBuCzpPhTrz. In doped films, the compounds reach high photoluminescence quantum yields (ΦPL) of 91 and 81%, respectively. The chiroptical properties reveal dissymmetry factors |gPL| of up to 5 ? 10?4. These results demonstrate the impact of the cyclophane for the development of CP-TADF materials and add to the currently limited scope of available planar chiral donors.

AB - The prototypical example of a (cyclo)phane, [2.2]paracyclophane (PCP), has proven to be a versatile stereogenic moiety within the design of circularly polarized thermally activated delayed fluorescence (CP-TADF) emitters; however, the exploration of other cyclophanes within CP-TADF emitter design has been largely neglected. Here, a comparative study of the photophysical and optoelectronic properties of two cyclophane emitters, (1,7)tBuCzpPhTrz and its isomer (1,4)tBuCzpPhTrz, is presented. The carbazolophane-triazine compound (1,7)tBuCzpPhTrz, obtained via an unprecedented intramolecular rearrangement, is the first example of a planar chiral TADF emitter deviating from the PCP scaffold. Significant geometrical change of the enclosed carbazole in (1,7)tBuCzp results in an attenuation of the donor strength, while the merits of rigidity and steric bulk remain. In particular, the full width at half maximum (FWHM) of the photoluminescence spectrum in toluene of (1,7)tBuCzpPhTrz is reduced by 34% and blue-shifted by 20 nm compared to that of (1,4)tBuCzpPhTrz. In doped films, the compounds reach high photoluminescence quantum yields (ΦPL) of 91 and 81%, respectively. The chiroptical properties reveal dissymmetry factors |gPL| of up to 5 ? 10?4. These results demonstrate the impact of the cyclophane for the development of CP-TADF materials and add to the currently limited scope of available planar chiral donors.

KW - Carbazolophanes

KW - Circularly polarized luminescence

KW - Cyclophanes

KW - Organic light-emitting diodes

KW - Planar chirality

KW - Thermally activated delayed fluorescence

U2 - 10.1002/adfm.202401956

DO - 10.1002/adfm.202401956

M3 - Article

SN - 1616-301X

VL - EarlyView

JO - Advanced Functional Materials

JF - Advanced Functional Materials

ER -

A novel carbazolophane: a comparison of the performance of two planar chiral CP-TADF emitters

Abstract

Keywords

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MR TADF: Multi-resonance TADF materials for highly efficient and stable OLEDs

MR TADF: Multi-resonance TADF materials for highly efficient and stable OLEDs

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

Datasets

A Novel Carbazolophane: A Comparison of the Performance of Two Planar Chiral CPTADF Emitters (dataset)

Cite this