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An S-shaped double helicene showing both multi-resonance thermally activated delayed fluorescence and circularly polarized luminescence

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Date
28/03/2022
Author
Dos Santos, John
Sun, Dianming
Naranjo, Juan
Hall, David
Zinna, Francesco
Ryan, Seán
Shi, Wenda
Matulaitis, Tomas
Cordes, David Bradford
Slawin, Alexandra Martha Zoya
Beljonne, David
Warriner, Stuart
Olivier, Yoann
Fuchter, Matthew
Zysman-Colman, Eli
Funder
The Leverhulme Trust
European Commission
EPSRC
The Royal Society
Grant ID
RPG-2016-047
838009
EP/P010482/1
SRF\R1\201089
Keywords
Chirality
Circular dichroism
Circularly polarized luminescence
Helical structure
Helicene
Multi-resonant thermally activated delayed fluorescence
Narrow emission
TADF
QD Chemistry
DAS
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Abstract
We present the first example of a multi-resonant thermally activated delayed fluorescent (MR-TADF) extended helicene, Hel-DiDiKTa. This S-shaped double helicene exhibits sky-blue emission, a singlet-triplet energy gap, ΔEST, of 0.15 eV and narrow emission at a peak maximum of 473 nm with a full-width at half-maximum of 44 nm in toluene. The MR-TADF character is confirmed by the small degree of positive solvatochromism and temperature-dependent increase in intensity of the delayed emission. The chiroptical properties of the separated enantiomers are similar to other large helicenes with comparable dissymmetry values, but with the added benefit of MR-TADF. (P)-Hel-DiDiKTa is stable towards enantiomerization, with a Gibbs free energy of activation for enantiomerization (ΔGe‡) of 31± 2 kcal mol-1 at 298 K, a value similar to other reported double helicenes. (P)-Hel-DiDiKTa is also thermally stable, with a 5% weight loss at 399 oC revealed by thermogravimetric analysis (TGA). Thus, this study further strengthens the burgeoning area of chiral TADF emitters for use in cutting-edge optoelectronic and photocatalytic molecules and materials.
Citation
Dos Santos , J , Sun , D , Naranjo , J , Hall , D , Zinna , F , Ryan , S , Shi , W , Matulaitis , T , Cordes , D B , Slawin , A M Z , Beljonne , D , Warriner , S , Olivier , Y , Fuchter , M & Zysman-Colman , E 2022 , ' An S-shaped double helicene showing both multi-resonance thermally activated delayed fluorescence and circularly polarized luminescence ' , Journal of Materials Chemistry C , vol. 10 , no. 12 , pp. 4861-4870 . https://doi.org/10.1039/D2TC00198E
Publication
Journal of Materials Chemistry C
Status
Peer reviewed
DOI
https://doi.org/10.1039/D2TC00198E
ISSN
2050-7526
Type
Journal article
Rights
Copyright © 2022 The Author(s). Open Access Article. This article is licensed under aCreative Commons Attribution 3.0 Unported Licence.
Description
Funding: Scottish Funding Council (SFC/AN/08/020), Leverhulme Trust (RPG-2016-047), H2020 Marie Skłodowska-Curie Actions (838009, 859752), UK Engineering and Physical Sciences Research Council (EP/P010482/1, EP/R00188X/1), Royal Society (SRF\R1\201089), Fonds De La Recherche Scientifique - FNRS (2.5020.11, F.4534.21), Università di Pisa (PRA 2020_21).
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/25343

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