A chiral propeller-shaped triple helicene shows multi-resonant thermally activated delayed fluorescence

Jingxiang Wang; Jhon Sebastian Oviedo  Ortiz; Aidan McKay; David Bradford Cordes; Jeanne   Crassous; Eli Zysman-Colman

doi:10.1002/hlca.202400129

A chiral propeller-shaped triple helicene shows multi-resonant thermally activated delayed fluorescence

Jingxiang Wang, Jhon Sebastian Oviedo Ortiz, Aidan McKay, David Bradford Cordes, Jeanne Crassous, Eli Zysman-Colman^*

^*Corresponding author for this work

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

Abstract

Multi-resonant thermally activated delayed fluorescence (MR-TADF) helicenes show great potential as chiral emitters due to their typically high photoluminescence quantum yield and that they emit circularly polarized luminescence. Here, a new propeller-shaped chiral MR TADF helicene DiKTa3, integrating three DiKTa moieties, was designed and synthesized aiming to achieve co-parallel electronic and magnitude transition dipole moments that would lead to a high dissymmetry factor, g. It emits at λ_PL of 491 nm, with a full width at half maximum of 52 nm and has a moderate ΔE_ST value of 0.24 eV in toluene. The separated (P,P,P) enantiomer shows an absorption dissymmetry factor |g_abs| of 6.8 × 10^-4 23 at 450 nm, which results from a lower symmetry conformation adopted by the compound in solution than the C₃-symmetric optimized structure. This work highlights the strong influence that geometry can
have on the chiroptical properties of the emitter.

Original language	English
Article number	e202400129
Number of pages	11
Journal	Helvetica Chimica Acta
Volume	Early View
Early online date	31 Oct 2024
DOIs	https://doi.org/10.1002/hlca.202400129
Publication status	E-pub ahead of print - 31 Oct 2024

Keywords

Chirality
Helicene
Circular dichronism
Circularly polarized lumninescence
Multi-resonant thermally activated delayed fluorescence

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10.1002/hlca.202400129Licence: CC BY

Wang_2024_Helv_Chiral-propeller-shaped-triple-helicene_CC
Copyright © 2024 The Authors. This is an open access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 9.78 MBLicence: CC BY

1 Finished
2 Active

Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. (PI), Morris, R. (CoI), Smith, A. (CoI) & Zysman-Colman, E. (CoI)
UK Research and Innovation
1/05/23 → 30/04/28
Project: Standard
TADF Solutions: TADF SOLUTIONS: addressing the challenges of high-performance solution-processed OLEDs using sustainable materials
Zysman-Colman, E. (PI)
UKRI (EU)
1/10/22 → 30/09/26
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

A Chiral Propeller-Shaped Triple Helicene Shows Multi-1 Resonant Thermally Activated 2 Delayed Fluorescence (dataset)
Wang, J. (Creator), Oviedo Ortiz, J. S. (Creator), McKay, A. (Creator), Cordes, D. B. (Creator), Crassous, J. (Creator) & Zysman-Colman, E. (Creator), University of St Andrews, 15 Oct 2024
DOI: 10.17630/a3917a0d-9839-4465-8c51-f89d4a0fd44d
Dataset

File

Design and synthesis of multi-resonant thermally activated delayed fluorescence materials and chiral emitters
Wang, J. (Author), Zysman-Colman, E. (Supervisor), 3 Jul 2025
Student thesis: Doctoral Thesis (PhD)

Cite this

@article{ead95b53f7cf41ea891669972700cfb9,

title = "A chiral propeller-shaped triple helicene shows multi-resonant thermally activated delayed fluorescence",

abstract = "Multi-resonant thermally activated delayed fluorescence (MR-TADF) helicenes show great potential as chiral emitters due to their typically high photoluminescence quantum yield and that they emit circularly polarized luminescence. Here, a new propeller-shaped chiral MR TADF helicene DiKTa3, integrating three DiKTa moieties, was designed and synthesized aiming to achieve co-parallel electronic and magnitude transition dipole moments that would lead to a high dissymmetry factor, g. It emits at λPL of 491 nm, with a full width at half maximum of 52 nm and has a moderate ΔEST value of 0.24 eV in toluene. The separated (P,P,P) enantiomer shows an absorption dissymmetry factor |gabs| of 6.8 × 10-4 23 at 450 nm, which results from a lower symmetry conformation adopted by the compound in solution than the C3-symmetric optimized structure. This work highlights the strong influence that geometry can have on the chiroptical properties of the emitter.",

keywords = "Chirality, Helicene, Circular dichronism, Circularly polarized lumninescence, Multi-resonant thermally activated delayed fluorescence",

author = "Jingxiang Wang and Ortiz, {Jhon Sebastian Oviedo} and Aidan McKay and Cordes, {David Bradford} and Jeanne Crassous and Eli Zysman-Colman",

note = "Funding: J.W. thanks the China Scholarship Council (202006250026). This project has been partly funded by the European Union Horizon 2021 research and innovation programme under grant agreement No. 101073045 (TADFsolutions) and the EPSRC grant EP/X026175/1 . J.C. acknowledge the Minist{\`e}re de l'Enseignement Sup{\'e}rieur et de la Recherche and the Centre National de la Recherche Scientifique (CNRS). The St Andrews team acknowledges the Engineering and Physical Sciences Research Council of the UK for support through grants EP/P010482/1 and EP/W007517/1).",

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doi = "10.1002/hlca.202400129",

language = "English",

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journal = "Helvetica Chimica Acta",

issn = "0018-019X",

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T1 - A chiral propeller-shaped triple helicene shows multi-resonant thermally activated delayed fluorescence

AU - Wang, Jingxiang

AU - Ortiz, Jhon Sebastian Oviedo

AU - McKay, Aidan

AU - Cordes, David Bradford

AU - Crassous, Jeanne

AU - Zysman-Colman, Eli

N1 - Funding: J.W. thanks the China Scholarship Council (202006250026). This project has been partly funded by the European Union Horizon 2021 research and innovation programme under grant agreement No. 101073045 (TADFsolutions) and the EPSRC grant EP/X026175/1 . J.C. acknowledge the Ministère de l'Enseignement Supérieur et de la Recherche and the Centre National de la Recherche Scientifique (CNRS). The St Andrews team acknowledges the Engineering and Physical Sciences Research Council of the UK for support through grants EP/P010482/1 and EP/W007517/1).

PY - 2024/10/31

Y1 - 2024/10/31

N2 - Multi-resonant thermally activated delayed fluorescence (MR-TADF) helicenes show great potential as chiral emitters due to their typically high photoluminescence quantum yield and that they emit circularly polarized luminescence. Here, a new propeller-shaped chiral MR TADF helicene DiKTa3, integrating three DiKTa moieties, was designed and synthesized aiming to achieve co-parallel electronic and magnitude transition dipole moments that would lead to a high dissymmetry factor, g. It emits at λPL of 491 nm, with a full width at half maximum of 52 nm and has a moderate ΔEST value of 0.24 eV in toluene. The separated (P,P,P) enantiomer shows an absorption dissymmetry factor |gabs| of 6.8 × 10-4 23 at 450 nm, which results from a lower symmetry conformation adopted by the compound in solution than the C3-symmetric optimized structure. This work highlights the strong influence that geometry can have on the chiroptical properties of the emitter.

AB - Multi-resonant thermally activated delayed fluorescence (MR-TADF) helicenes show great potential as chiral emitters due to their typically high photoluminescence quantum yield and that they emit circularly polarized luminescence. Here, a new propeller-shaped chiral MR TADF helicene DiKTa3, integrating three DiKTa moieties, was designed and synthesized aiming to achieve co-parallel electronic and magnitude transition dipole moments that would lead to a high dissymmetry factor, g. It emits at λPL of 491 nm, with a full width at half maximum of 52 nm and has a moderate ΔEST value of 0.24 eV in toluene. The separated (P,P,P) enantiomer shows an absorption dissymmetry factor |gabs| of 6.8 × 10-4 23 at 450 nm, which results from a lower symmetry conformation adopted by the compound in solution than the C3-symmetric optimized structure. This work highlights the strong influence that geometry can have on the chiroptical properties of the emitter.

KW - Chirality

KW - Helicene

KW - Circular dichronism

KW - Circularly polarized lumninescence

KW - Multi-resonant thermally activated delayed fluorescence

U2 - 10.1002/hlca.202400129

DO - 10.1002/hlca.202400129

M3 - Article

SN - 0018-019X

VL - Early View

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

M1 - e202400129

ER -

A chiral propeller-shaped triple helicene shows multi-resonant thermally activated delayed fluorescence

Abstract

Keywords

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Projects

Allan Watson Programme Grant: Boron: Beyond the Reagent

TADF Solutions: TADF SOLUTIONS: addressing the challenges of high-performance solution-processed OLEDs using sustainable materials

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

Datasets

A Chiral Propeller-Shaped Triple Helicene Shows Multi-1 Resonant Thermally Activated 2 Delayed Fluorescence (dataset)

Student theses

Design and synthesis of multi-resonant thermally activated delayed fluorescence materials and chiral emitters

Cite this