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Issue 14, 2021
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Porous shape-persistent rylene imine cages with tunable optoelectronic properties and delayed fluorescence

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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.

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

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Supplementary files

Article information


Submitted
19 Jan 2021
Accepted
10 Feb 2021
First published
09 Mar 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 5275-5285
Article type
Edge Article

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

H. Huang, K. S. Song, A. Prescimone, A. Aster, G. Cohen, R. Mannancherry, E. Vauthey, A. Coskun and T. Šolomek, Chem. Sci., 2021, 12, 5275
DOI: 10.1039/D1SC00347J

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