σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals

Catherine Demangeat; Yixuan Dou; Bin Hu; Yann Bretonnière; Chantal Andraud; Anthony D'Aléo; Jeong Weon Wu; Eunkyoung Kim; Tangui Le Bahers; André Jean Attias

doi:10.1002/anie.202011770

σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals

Catherine Demangeat, Yixuan Dou, Bin Hu, Yann Bretonnière, Chantal Andraud, Anthony D'Aléo, Jeong Weon Wu, Eunkyoung Kim, Tangui Le Bahers, André Jean Attias

Department of Chemical and Biomolecular Engineering

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

19 Citations (Scopus)

Abstract

Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.

Original language	English
Pages (from-to)	2446-2454
Number of pages	9
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	5
DOIs	https://doi.org/10.1002/anie.202011770
Publication status	Published - 2021 Feb 1

Bibliographical note

Funding Information:
This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386‐17‐1‐4060). We are very grateful to Prof. Ha‐Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA Pôle de Compétitivité for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean‐Louis Fave (INSP, Université Sorbonne Université, Paris) for the very fruitful and friendly discussions.

Funding Information:
This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386-17-1-4060). We are very grateful to Prof. Ha-Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA P?le de Comp?titivit? for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean-Louis Fave (INSP, Universit? Sorbonne Universit?, Paris) for the very fruitful and friendly discussions.

Publisher Copyright:
© 2020 Wiley-VCH GmbH

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/anie.202011770

Cite this

Demangeat, C., Dou, Y., Hu, B., Bretonnière, Y., Andraud, C., D'Aléo, A., Wu, J. W., Kim, E., Le Bahers, T., & Attias, A. J. (2021). σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals. Angewandte Chemie - International Edition, 60(5), 2446-2454. https://doi.org/10.1002/anie.202011770

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title = "σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals",

abstract = "Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.",

author = "Catherine Demangeat and Yixuan Dou and Bin Hu and Yann Bretonni{\`e}re and Chantal Andraud and Anthony D'Al{\'e}o and Wu, {Jeong Weon} and Eunkyoung Kim and {Le Bahers}, Tangui and Attias, {Andr{\'e} Jean}",

note = "Funding Information: This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386‐17‐1‐4060). We are very grateful to Prof. Ha‐Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA P{\^o}le de Comp{\'e}titivit{\'e} for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean‐Louis Fave (INSP, Universit{\'e} Sorbonne Universit{\'e}, Paris) for the very fruitful and friendly discussions. Funding Information: This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386-17-1-4060). We are very grateful to Prof. Ha-Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA P?le de Comp?titivit? for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean-Louis Fave (INSP, Universit? Sorbonne Universit?, Paris) for the very fruitful and friendly discussions. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

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Demangeat, C, Dou, Y, Hu, B, Bretonnière, Y, Andraud, C, D'Aléo, A, Wu, JW, Kim, E, Le Bahers, T & Attias, AJ 2021, 'σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals', Angewandte Chemie - International Edition, vol. 60, no. 5, pp. 2446-2454. https://doi.org/10.1002/anie.202011770

σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly : Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals. / Demangeat, Catherine; Dou, Yixuan; Hu, Bin et al.

In: Angewandte Chemie - International Edition, Vol. 60, No. 5, 01.02.2021, p. 2446-2454.

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

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AU - Hu, Bin

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AU - D'Aléo, Anthony

AU - Wu, Jeong Weon

AU - Kim, Eunkyoung

AU - Le Bahers, Tangui

AU - Attias, André Jean

N1 - Funding Information: This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386‐17‐1‐4060). We are very grateful to Prof. Ha‐Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA Pôle de Compétitivité for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean‐Louis Fave (INSP, Université Sorbonne Université, Paris) for the very fruitful and friendly discussions. Funding Information: This research was supported by the Asian Office of Aerospace Research and Development (AOARD, FA 2386-17-1-4060). We are very grateful to Prof. Ha-Jin Lee from the Korea Basic Science Institute (KBSI, Western Seoul Center) for the single crystal measurements. The authors thank the SYSPROD project and AXELERA P?le de Comp?titivit? for financial support (PSMN Data Center). J.W.W. acknowledges NRF grant (2017R1E1A1A01075394, 2014M3A6B3063708). A.J.A. and C.D. thank Dr. Jean-Louis Fave (INSP, Universit? Sorbonne Universit?, Paris) for the very fruitful and friendly discussions. Publisher Copyright: © 2020 Wiley-VCH GmbH

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N2 - Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.

AB - Long-lived room temperature phosphorescence from organic molecular crystals attracts great attention. Persistent luminescence depends on the electronic properties of the molecular components, mainly π-conjugated donor–acceptor (D-A) chromophores, and their molecular packing. Here, a strategy is developed by designing two isomeric molecular phosphors incorporating and combining a bridge for σ-conjugation between the D and A units and a structure-directing unit for H-bond-directed supramolecular self-assembly. Calculations highlight the critical role played by the two degrees of freedom of the σ-conjugated bridge on the chromophore optical properties. The molecular crystals exhibit RTP quantum yields up to 20 % and lifetimes up to 520 ms. The crystal structures of the efficient phosphorescent materials establish the existence of an unprecedented well-organization of the emitters into 2D rectangular columnar-like supramolecular structure stabilized by intermolecular H-bonding.

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σ-Conjugation and H-Bond-Directed Supramolecular Self-Assembly: Key Features for Efficient Long-Lived Room Temperature Phosphorescent Organic Molecular Crystals

Abstract

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