Organic Chemistry, Short talk
OC-026

Synthesis of chiral and redox-active covalent organic cages

H. Huang1, T. Šolomek1*
1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland

Porous organic materials have been discovered roughly a decade ago but rapidly developed because they possess several attractive features as gas storage or separation materials.1-2 For example, porous organic cages have an intrinsic cavity and can be crystallized with permanent voids that allow access for guest molecules to get adsorbed inside the crystal. These types of molecules can, therefore, behave like a zeolite because of the porosity but offer processability typical for organic compounds.

Porous organic cages are typically assembled by dynamic covalent chemistry3 (DCC) that allows for error correction in the cage formation. Recently, we have synthesized a series of chiral covalent organic cages with three built-in redox-active rylene-based units by dynamic imine chemistry.4 Structural characterizations were carried out via NMR and single-crystal X-ray diffraction, which demonstrated the three-dimensional structure prevents the three redox-active units from aggregation. The structure of these cages allowed us to investigate their properties in applications, such as gas adsorption and separation with promising results. This contribution will reveal our early achievements and will discuss our findings regarding the formation of the rylene cages and their new exciting derivatives. Our investigations show a great potential of our organic cages in applications beyond the host-guest chemistry.

[1]Tom Hasell, Andrew I. Cooper, Nature Reviews20161, 1-14.
[2]Florian Beuerle, Bappadity Gole, Angewandte Chemie International Edition2018, 57, 4850-4878.
[3]Mathew E. Belowich, J. Fraser Stoddart, Chemical Society Reviews201241, 2003-2024.
[4] a.) Tomáš Šolomek, Natalia E. Powers-Riggs, Yi-Lin Wu, Ryan M. Young, Matthew D. Krzyaniak, Noah E. Horwitz, Michael R. Wasielewski, Journal of the American Chemical Society2017139, 3348-3351.; b.) Hsin-Hua Huang, Kyung Seob Song, Alessandro Prescimone, Rajesh Mannancherry, Ali Coskun, Tomáš Šolomek, manuscript in preparation.