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Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution

Catherine Demangeat, Maxime Rémond, John Hudson, Emrys Evans Orcid Logo, Denis Jacquemin, Ludovic Favereau Orcid Logo

Angewandte Chemie International Edition, Start page: e202515218

Swansea University Authors: John Hudson, Emrys Evans Orcid Logo

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DOI (Published version): 10.1002/anie.202515218

Abstract

The development of purely organic chiral room temperature phosphorescence (RTP) emitters is attracting more and more attention. However, the key parameters governing the polarized luminescence process remain difficult to predict and rationalize since the phosphorescence emission is rarely obtained i...

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Published in: Angewandte Chemie International Edition
ISSN: 1433-7851 1521-3773
Published: Wiley 2025
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URI: https://cronfa.swan.ac.uk/Record/cronfa70634
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spelling 2025-10-10T14:21:41.1589531 v2 70634 2025-10-10 Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution 38b3b5cb9a12e7c876078c774f87e979 John Hudson John Hudson true false 538e217307dac24c9642ef1b03b41485 0000-0002-9092-3938 Emrys Evans Emrys Evans true false 2025-10-10 PGRO The development of purely organic chiral room temperature phosphorescence (RTP) emitters is attracting more and more attention. However, the key parameters governing the polarized luminescence process remain difficult to predict and rationalize since the phosphorescence emission is rarely obtained in solution, hampering any structure‐relationship studies. To address this challenge, we report here the synthesis and chiroptical properties of a new family of metal‐free phosphorescent emitters based on phthalimide derivatives. Breaking symmetry of the phthalimide units and using intra‐ and intermolecular hydrogen bonding enable the obtention of circularly polarized (CP) RTP in solution with glum of up to 5 × 10−3. Interestingly, our investigations demonstrate the intricate role of hydrogen bonding interactions in modulating triplet state generation through the mixing of singlet and triplet states of different nature, i.e., n‐π* and π–π*, in the excited state, which is a crucial parameter for achieving intense CP‐RTP. These results bring additional molecular design guidelines to reach CP‐RTP in solution and additionally offer new insights into the subtle relationships between excited states of different spin multiplicity to reach higher CP phosphorescence intensity. Journal Article Angewandte Chemie International Edition 0 e202515218 Wiley 1433-7851 1521-3773 Organic chiral emitters; Room temperature circularly polarized phosphorescence; Spin orbit coupling; Symmetry breaking 9 10 2025 2025-10-09 10.1002/anie.202515218 COLLEGE NANME Postgraduate Research Office COLLEGE CODE PGRO Swansea University Another institution paid the OA fee Région Bretagne (PhoChiRad BIENVENÜE Call 2023); European Union; Royal Society University Fellowship (URF/R1/201300); EPSRC (EP/Y002555/1) 2025-10-10T14:21:41.1589531 2025-10-10T14:04:23.7193768 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Catherine Demangeat 1 Maxime Rémond 2 John Hudson 3 Emrys Evans 0000-0002-9092-3938 4 Denis Jacquemin 5 Ludovic Favereau 0000-0001-7847-2911 6 70634__35309__d40af4e1a5074566a76fff2cf88b8f4f.pdf anie.202515218.pdf 2025-10-10T14:04:23.6949239 Output 1896247 application/pdf Version of Record true © 2025 The Author(s). This is an open access article under the terms of the Creative Commons Attribution License (CC BY). true eng http://creativecommons.org/licenses/by/4.0/
title Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
spellingShingle Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
John Hudson
Emrys Evans
title_short Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
title_full Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
title_fullStr Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
title_full_unstemmed Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
title_sort Symmetry Breaking and Hydrogen Bonding in Phthalimide Compounds Enable Efficient Room‐Temperature Circularly Polarized Phosphorescence in Solution
author_id_str_mv 38b3b5cb9a12e7c876078c774f87e979
538e217307dac24c9642ef1b03b41485
author_id_fullname_str_mv 38b3b5cb9a12e7c876078c774f87e979_***_John Hudson
538e217307dac24c9642ef1b03b41485_***_Emrys Evans
author John Hudson
Emrys Evans
author2 Catherine Demangeat
Maxime Rémond
John Hudson
Emrys Evans
Denis Jacquemin
Ludovic Favereau
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container_title Angewandte Chemie International Edition
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container_start_page e202515218
publishDate 2025
institution Swansea University
issn 1433-7851
1521-3773
doi_str_mv 10.1002/anie.202515218
publisher Wiley
college_str Faculty of Science and Engineering
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hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
document_store_str 1
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description The development of purely organic chiral room temperature phosphorescence (RTP) emitters is attracting more and more attention. However, the key parameters governing the polarized luminescence process remain difficult to predict and rationalize since the phosphorescence emission is rarely obtained in solution, hampering any structure‐relationship studies. To address this challenge, we report here the synthesis and chiroptical properties of a new family of metal‐free phosphorescent emitters based on phthalimide derivatives. Breaking symmetry of the phthalimide units and using intra‐ and intermolecular hydrogen bonding enable the obtention of circularly polarized (CP) RTP in solution with glum of up to 5 × 10−3. Interestingly, our investigations demonstrate the intricate role of hydrogen bonding interactions in modulating triplet state generation through the mixing of singlet and triplet states of different nature, i.e., n‐π* and π–π*, in the excited state, which is a crucial parameter for achieving intense CP‐RTP. These results bring additional molecular design guidelines to reach CP‐RTP in solution and additionally offer new insights into the subtle relationships between excited states of different spin multiplicity to reach higher CP phosphorescence intensity.
published_date 2025-10-09T18:09:06Z
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