Intermolecular interactions play a fundamental role on the performance of conjugated materials in organic electronic devices, as they heavily influence their optoelectronic properties. Synthetic control over the solid state properties of organic optoelectronic materials is crucial to access real life applications. Perylene diimides (PDIs) are one of the most highly studied classes of organic fluorescent dyes. In the solid state, π-πstacking suppresses their emission, limiting their use in a variety of applications. Here, we report the synthesis of a novel PDI dye that is encapsulated by four alkylene straps. X-ray crystallography indicates that intermolecular π-πstacking is completely suppressed in the crystalline state. This is further validated by the photophysical properties of the dye in both solution and solid state and supported by theoretical calculations. However, we find that the introduction of the encapsulating "arms" results in the creation of charge-transfer states which modify the excited state properties. This article demonstrates that molecular encapsulation can be used as a powerful tool to tune intermolecular interactions and thereby gain an extra level of control over the solid state properties of organic optoelectronic materials.

Royakkers, J., Minotto, A., Congrave, D., Zeng, W., Patel, A., Bond, A., et al. (2020). Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties. JOURNAL OF ORGANIC CHEMISTRY, 85(1), 207-214 [10.1021/acs.joc.9b02597].

Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties

Minotto, A;
2020

Abstract

Intermolecular interactions play a fundamental role on the performance of conjugated materials in organic electronic devices, as they heavily influence their optoelectronic properties. Synthetic control over the solid state properties of organic optoelectronic materials is crucial to access real life applications. Perylene diimides (PDIs) are one of the most highly studied classes of organic fluorescent dyes. In the solid state, π-πstacking suppresses their emission, limiting their use in a variety of applications. Here, we report the synthesis of a novel PDI dye that is encapsulated by four alkylene straps. X-ray crystallography indicates that intermolecular π-πstacking is completely suppressed in the crystalline state. This is further validated by the photophysical properties of the dye in both solution and solid state and supported by theoretical calculations. However, we find that the introduction of the encapsulating "arms" results in the creation of charge-transfer states which modify the excited state properties. This article demonstrates that molecular encapsulation can be used as a powerful tool to tune intermolecular interactions and thereby gain an extra level of control over the solid state properties of organic optoelectronic materials.
Articolo in rivista - Articolo scientifico
Dyes and pigments; Hydrocarbons; Thin films; Encapsulation; Aromatic compounds
English
4-nov-2019
2020
85
1
207
214
open
Royakkers, J., Minotto, A., Congrave, D., Zeng, W., Patel, A., Bond, A., et al. (2020). Doubly Encapsulated Perylene Diimides: Effect of Molecular Encapsulation on Photophysical Properties. JOURNAL OF ORGANIC CHEMISTRY, 85(1), 207-214 [10.1021/acs.joc.9b02597].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/340941
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