Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence

Jeroen Royakkers; Kunping Guo; Daniel T.W. Toolan; Liang Wen Feng; Alessandro Minotto; Daniel G. Congrave; Magda Danowska; Weixuan Zeng; Andrew D. Bond; Mohammed Al-Hashimi; Tobin J. Marks; Antonio Facchetti; Franco Cacialli; Hugo Bronstein

doi:10.1002/anie.202110139

Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence

Jeroen Royakkers, Kunping Guo, Daniel T.W. Toolan, Liang Wen Feng, Alessandro Minotto, Daniel G. Congrave, Magda Danowska, Weixuan Zeng, Andrew D. Bond, Mohammed Al-Hashimi, Tobin J. Marks, Antonio Facchetti, Franco Cacialli, Hugo Bronstein^*

^*Corresponding author for this work

Chemistry

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

18 Scopus citations

Abstract

Conjugated polymers are an important class of chromophores for optoelectronic devices. Understanding and controlling their excited state properties, in particular, radiative and non-radiative recombination processes are among the greatest challenges that must be overcome. We report the synthesis and characterization of a molecularly encapsulated naphthalene diimide-based polymer, one of the most successfully used motifs, and explore its structural and optical properties. The molecular encapsulation enables a detailed understanding of the effect of interpolymer interactions. We reveal that the non-encapsulated analogue P(NDI-2OD-T) undergoes aggregation enhanced emission; an effect that is suppressed upon encapsulation due to an increasing π-interchain stacking distance. This suggests that decreasing π-stacking distances may be an attractive method to enhance the radiative properties of conjugated polymers in contrast to the current paradigm where it is viewed as a source of optical quenching.

Original language	English (US)
Pages (from-to)	25005-25012
Number of pages	8
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	47
DOIs	https://doi.org/10.1002/anie.202110139
State	Published - Nov 15 2021

Funding

We gratefully acknowledge funding by EPRSC (Grants EP/P007767/1, EP/S003126/1, and EP/P006280/1), Qatar National Research Grant NPRP 12S0304-190227, U.S. Office of Naval Research Contract N00014-20-2116, the Royal Society (Newton International Fellowship to K.G.), and the Winton Programme for the Physics of Sustainability. This work was carried out with the support of Diamond Light Source, instrument I07 (proposal SI23587-1). We gratefully acknowledge funding by EPRSC (Grants EP/P007767/1, EP/S003126/1, and EP/P006280/1), Qatar National Research Grant NPRP 12S0304‐190227, U.S. Office of Naval Research Contract N00014‐20‐2116, the Royal Society (Newton International Fellowship to K.G.), and the Winton Programme for the Physics of Sustainability. This work was carried out with the support of Diamond Light Source, instrument I07 (proposal SI23587‐1).

Keywords

conjugated polymers
encapsulation
macrocycles
organic electronics
photoluminescence

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.202110139

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Royakkers, J., Guo, K., Toolan, D. T. W., Feng, L. W., Minotto, A., Congrave, D. G., Danowska, M., Zeng, W., Bond, A. D., Al-Hashimi, M., Marks, T. J., Facchetti, A., Cacialli, F., & Bronstein, H. (2021). Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence. Angewandte Chemie - International Edition, 60(47), 25005-25012. https://doi.org/10.1002/anie.202110139

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abstract = "Conjugated polymers are an important class of chromophores for optoelectronic devices. Understanding and controlling their excited state properties, in particular, radiative and non-radiative recombination processes are among the greatest challenges that must be overcome. We report the synthesis and characterization of a molecularly encapsulated naphthalene diimide-based polymer, one of the most successfully used motifs, and explore its structural and optical properties. The molecular encapsulation enables a detailed understanding of the effect of interpolymer interactions. We reveal that the non-encapsulated analogue P(NDI-2OD-T) undergoes aggregation enhanced emission; an effect that is suppressed upon encapsulation due to an increasing π-interchain stacking distance. This suggests that decreasing π-stacking distances may be an attractive method to enhance the radiative properties of conjugated polymers in contrast to the current paradigm where it is viewed as a source of optical quenching.",

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Royakkers, J, Guo, K, Toolan, DTW, Feng, LW, Minotto, A, Congrave, DG, Danowska, M, Zeng, W, Bond, AD, Al-Hashimi, M, Marks, TJ, Facchetti, A, Cacialli, F & Bronstein, H 2021, 'Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence', Angewandte Chemie - International Edition, vol. 60, no. 47, pp. 25005-25012. https://doi.org/10.1002/anie.202110139

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AU - Feng, Liang Wen

AU - Minotto, Alessandro

AU - Congrave, Daniel G.

AU - Danowska, Magda

AU - Zeng, Weixuan

AU - Bond, Andrew D.

AU - Al-Hashimi, Mohammed

AU - Marks, Tobin J.

AU - Facchetti, Antonio

AU - Cacialli, Franco

AU - Bronstein, Hugo

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Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence

Abstract

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CCDC 2079163: Experimental Crystal Structure Determination

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Molecular Encapsulation of Naphthalene Diimide (NDI) Based π-Conjugated Polymers: A Tool for Understanding Photoluminescence

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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CCDC 2079163: Experimental Crystal Structure Determination

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