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Porous shape-persistent rylene imine cages with tunable optoelectronic properties and delayed fluorescence

Contributors

Huang, Hsin-Hua; Song, Kyung Seob; Prescimone, Alessandro; Aster, Alexander; Cohen, Gabriel; Mannancherry, Rajesh; Vauthey, Eric; Coskun, Ali; Šolomek, Tomáš

Published in

Chemical Science, vol. 12, p. 5275-5285

Publication date

2021

Abstract

A simultaneous combination of porosity and tunable optoelectronic properties, common in covalent organic frameworks, is rare in shape-persistent organic cages. Yet, organic cages offer important molecular advantages such as solubility and modularity. Herein, we report the synthesis of a series of chiral imine organic cages with three built-in rylene units by means of dynamic imine chemistry and we investigate their textural and optoelectronic properties. Thereby we demonstrate that the synthesized rylene cages can be reversibly reduced at accessible potentials, absorb from UV up to green light, are porous, and preferentially adsorb CO2 over N2 and CH4 with a good selectivity. In addition, we discovered that the cage incorporating three perylene-3,4:9,10-bis(dicarboximide) units displays an efficient delayed fluorescence. Time-correlated single photon counting and transient absorption spectroscopy measurements suggest that the delayed fluorescence is likely a consequence of a reversible intracage charge-separation event. Rylene cages thus offer a promising platform that allows combining the porosity of processable materials and photochemical phenomena useful in diverse applications such as photocatalysis or energy storage.

UNIGE affiliation entities

UNIGE research groups

Funding

Citation (ISO format)

HUANG, Hsin-Hua et al. Porous shape-persistent rylene imine cages with tunable optoelectronic properties and delayed fluorescence. In: Chemical Science, 2021, vol. 12, p. 5275–5285. doi: 10.1039/D1SC00347J

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Article (Published version)
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Identifiers

Additional URL for this publication

http://xlink.rsc.org/?DOI=D1SC00347J

Journal ISSN

2041-6520
340views
409downloads

Technical informations

Creation

15/04/2021 13:36:00

First validation

15/04/2021 13:36:00

Update

30/03/2023 11:08:34

Status update

30/03/2023 11:08:33

Last indexation

31/10/2024 21:50:55
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