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Herein, we report a facile postsynthetic linkage conversion method giving synthetic access to nitrone-linked covalent organic frameworks (COFs) from imine- and amine-linked COFs. The new two-dimensional (2D) nitrone-linked covalent organic frameworks, NO-PI-3-COF and NO-TTI-COF, are obtained with high crystallinity and large surface areas. Nitrone-modified pore channels induce condensation of water vapor at 20% lower humidity compared to their amine- or imine-linked precursor COFs. Thus, the topochemical transformation to nitrone linkages constitutes an attractive approach to postsynthetically fine-tune water adsorption properties in framework materials.
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http://dx.doi.org/10.1021/jacs.3c02572 | DOI Listing |
Angew Chem Int Ed Engl
September 2023
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.
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 C multi cross-polarization magic angle spinning NMR spectroscopy of the C-isotope-labeled COF-115 and Fourier-transform infrared spectroscopy. The permanent porosity of COF-115 was evaluated through low-pressure N , CO , and H sorption experiments.
View Article and Find Full Text PDFJ Am Chem Soc
July 2023
Department of Materials Science and Engineering, City University of Hong Kong, Hong Kong SAR 999077, P. R. China.
Developing diverse synthetic routes to prepare various crystalline covalent organic frameworks (COFs) and enrich the family of COFs is very important and highly desirable. In this research, we demonstrate that Kröhnke oxidation (originally developed to prepare carbonyl compounds) can be employed as an efficient method to construct two crystalline nitrone-linked COFs (CityU-1 and CityU-2) through the ingenious design of the polynitroso-containing precursors as well as the exquisite control of the polymerization conditions. The formation and structure of nitrone-based linkage units have been confirmed through a mode reaction.
View Article and Find Full Text PDFJ Am Chem Soc
June 2023
Max Planck Institute for Solid State Research, Heisenbergstraße 1, 70569 Stuttgart, Germany.
Herein, we report a facile postsynthetic linkage conversion method giving synthetic access to nitrone-linked covalent organic frameworks (COFs) from imine- and amine-linked COFs. The new two-dimensional (2D) nitrone-linked covalent organic frameworks, NO-PI-3-COF and NO-TTI-COF, are obtained with high crystallinity and large surface areas. Nitrone-modified pore channels induce condensation of water vapor at 20% lower humidity compared to their amine- or imine-linked precursor COFs.
View Article and Find Full Text PDFJ Am Chem Soc
October 2020
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
Many microorganisms possess the capacity for producing multiple antibiotic secondary metabolites. In a few notable cases, combinations of secondary metabolites produced by the same organism are used in important combination therapies for treatment of drug-resistant bacterial infections. However, examples of conjoined roles of bioactive metabolites produced by the same organism remain uncommon.
View Article and Find Full Text PDFChemistry
January 2008
UMR 6517 CNRS et Aix-Marseille Université, Faculté de Saint-Jérôme, Case 521, Avenue Escadrille Normandie Niemen, 13397, Marseille Cedex 20, France.
alpha-Phenyl-N-tert-butylnitrone (PBN) derivatives bound to beta-cyclodextrin derivatives have been synthesized. Inclusion of the PBN group into the beta-cyclodextrin moiety is host- and temperature-dependent. In the case of the nitrone linked to permethylated cyclodextrin (Me3CD-PBN), the thermokinetic parameters are in favour of a slow chemical exchange between a tight and a loose complex.
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