Inhibition by Water during Heterogeneous Brønsted Acid Catalysis by Three-Dimensional Crystalline Organic Salts

A new self-assembled and self-healing class of metal free, recyclable, heterogeneous Brønsted acid catalysts has been developed by the protonation of aniline derivatives (tetrakis(4-aminophenyl)methane, leuco-crystal violet, benzidine, and p-phenylenediamine) with aromatic sulfonic acids (tetrakis(phenyl-4-sulfonic acid)methane, and 2,6-naphthalenedisulfonic acid). As a result, five three-dimensional crystalline organic salts (F-1a, F-1b, F-1c, F-2, and F-3) were obtained, linked by hydrogen bonds and additionally stabilized by the opposite charges of the components. Frameworks F-2 and F-3 were prepared for the first time and characterized by elemental analysis, X-ray structural analysis (for F-2), thermogravimetry, SEM, and FTIR spectroscopy. The catalytic activities of crystalline organic salts F-1-3 have been explored in industrially important epoxide ring-opening and acetal formation reactions. The presence of encapsulated water inside frameworks F-1a and F-2 had an inhibitory effect on the performance of the catalysts. X-ray diffraction analysis of hydrated and dehydrated samples of F-1a and F-2 indicated that water of crystallization served as a cross-linking agent, diminishing the substrate induced "breathing"affinities of the frameworks. ©

Gak A.1, 2, 3 , Kuznetsova S.1 , Nelyubina Y.1 , Korlyukov A.A. 1 , Li H. 4 , North M. 4 , Zhereb V.5 , Riazanov V.6 , Peregudov A.S. 1 , Khakina E.1 , Lobanov N. 7 , Khrustalev V.N. 7, 8 , Belokon Y.N. 1
American Chemical Society
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  • 1 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, Moscow, 119991, Russian Federation
  • 2 Faculty of Material Science, Moscow State University, Leninskie Gory, 1/40, Moscow, 119991, Russian Federation
  • 3 National Research Nuclear University MEPhI, Institute of Nuclear Physics and Engineering, Kashirskoe shosse 31, Moscow, 115409, Russian Federation
  • 4 Green Chemistry Centre of Excellence, Department of Chemistry, University of York, York, Heslington, YO10 5DD, United Kingdom
  • 5 Siberian Federal University, School of Non-Ferrous Metals and Material Science, 95 Krasnoyarskiy Rabochiy pr., Krasnoyarsk, 660025, Russian Federation
  • 6 D. Mendeleev University of Chemical Technology of Russia, Miusskaya square 9, Moscow, 125047, Russian Federation
  • 7 Peoples' Friendship University of Russia, RUDN University, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
  • 8 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russian Federation
Ключевые слова
Aromatic compounds; Catalyst activity; Crosslinking; Fourier transform infrared spectroscopy; Hydrogen bonds; Methane; Salts; Thermogravimetric analysis; Acid catalysis; Acid catalyst; Aniline derivatives; Crystal violet; Metal free; Organic salt; Protonations; Recyclables; Self-healing; Tetrakis; Crystalline materials
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