Issue 14, 2021

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2021,12, 5275-5285

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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