Porous Shape-Persistent Rylene Imine Cages with Tunable Optoelectronic Properties and Delayed Fluorescence

16 September 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A simultaneous combination of porosity and tunable optoelectronic properties, common in covalent organic frameworks, are rare in shape-persistent organic cages. Yet, organic cages offer important molecular advantages, the 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 are porous, can be reversibly reduced at accessible potentials, and can absorb from UV up to green light. We also show that they 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 a delayed fluorescence, likely as a consequence of formation of a correlated triplet pair, the multiexciton state in singlet fission. Rylene cages thus represent a unique platform to investigate the effect of electronic properties on material porosity and, at the same time, to probe excited-state phenomena in the limit of vanishing interchromophore coupling.

Keywords

Shape-persistant organic cages
imine cages
porosity
optoelectronic properties
delayed fluorescence
perylene diimides

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.