A Porous Crystalline Nitrone-Linked Covalent Organic Framework

Daria Kurandina; Banruo Huang; Wentao Xu; Nikita Hanikel; Andrea Darù; Gautam D Stroscio; Kaiyu Wang; Laura Gagliardi; F Dean Toste; Omar M Yaghi

doi:10.1002/anie.202307674

A Porous Crystalline Nitrone-Linked Covalent Organic Framework

Angew Chem Int Ed Engl. 2023 Sep 4;62(36):e202307674. doi: 10.1002/anie.202307674. Epub 2023 Jul 24.

Authors

Affiliations

¹ Department of Chemistry and Kavli Energy Nanoscience Institute, University of California, Berkeley, Berkeley, CA, 94720, USA.
² Department of Chemistry, University of California, Berkley, Berkeley, CA, 94720, USA.
³ Department of Chemistry, Pritzker School of Molecular Engineering, Chicago Center for Theoretical Chemistry, University of Chicago, Chicago, IL, 60637, USA.
⁴ Department of Chemistry, Kavli Energy Nanoscience Institute and Bakar Institute of Digital Materials for the Planet, Division of Computing, Data Science, and Society, University of California, Berkeley, CA, 94720, USA.
⁵ UC Berkeley-KACST Joint Center of Excellence for Nanomaterials for Clean Energy Applications, King Abdulaziz City for Science and Technology, Riyadh, 11442, Saudi Arabia.

PMID: 37439285
DOI: 10.1002/anie.202307674

Abstract

Herein, we report the synthesis of a nitrone-linked covalent organic framework, COF-115, by combining N, N', N', N'''-(ethene-1, 1, 2, 2-tetrayltetrakis(benzene-4, 1-diyl))tetrakis(hydroxylamine) and terephthaladehyde via a polycondensation reaction. The formation of the nitrone functionality was confirmed by solid-state ¹³ C multi cross-polarization magic angle spinning NMR spectroscopy of the ¹³ C-isotope-labeled COF-115 and Fourier-transform infrared spectroscopy. The permanent porosity of COF-115 was evaluated through low-pressure N₂ , CO₂ , and H₂ sorption experiments. Water vapor and carbon dioxide sorption analysis of COF-115 and the isoreticular imine-linked COF indicated a superior potential of N-oxide-based porous materials for atmospheric water harvesting and CO₂ capture applications. Density functional theory calculations provided valuable insights into the difference between the adsorption properties of these COFs. Lastly, photoinduced rearrangement of COF-115 to the associated amide-linked material was successfully demonstrated.

Keywords: Atmospheric Water Harvesting; Covalent Organic Frameworks; Light Rearrangement; Nitrone.

Abstract

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