The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

The acid–base neutralization reaction of commercially available disodium 2,6-naphthalenedisulfonate (NDS, 2 equivalents) and the tetrahydrochloride salt of tetrakis(4-aminophenyl)methane (TAPM, 1 equivalent) in water gave a novel three-dimensional charge-assisted hydrogen-bonded framework (CAHOF, F-1). The framework F-1 was characterized by X-ray diffraction, TGA, elemental analysis, and 1H NMR spectroscopy. The framework was supported by hydrogen bonds between the sulfonate anions and the ammonium cations of NDS and protonated TAPM moieties, respectively. The CAHOF material functioned as a new type of catalytically active Brønsted acid in a series of reactions, including the ring opening of epoxides by water and alcohols. A Diels–Alder reaction between cyclopentadiene and methyl vinyl ketone was also catalyzed by F-1 in heptane. Depending on the polarity of the solvent mixture, the CAHOF F-1 could function as a purely heterogeneous catalyst or partly dissociate, providing some dissolved F-1 as the real catalyst. In all cases, the catalyst could easily be recovered and recycled. © 2020 Kuznetsova et al.

Kuznetsova S.A.1 , Gak A.S.2 , Nelyubina Y.V. 1 , Larionov V.A. 1, 3 , Li H. 4 , North M. 4 , Zhereb V.P.5 , Smol'yakov A.F. 1 , Dmitrienko A.O.1 , Medvedev M.G.1, 6 , Gerasimov I.S.1, 6 , Saghyan A.S.7 , Belokon Y.N. 1
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
  • 1 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, Moscow, 119991, Russian Federation
  • 2 Moscow State University, Faculty of Material Science, Leninskie Gory 1/73, Moscow, 119991, Russian Federation
  • 3 Department of Inorganic Chemistry, People’s Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
  • 4 Green Chemistry Centre of Excellence, Department of Chemistry, University of 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 N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prospect, 47, Moscow, 119991, Russian Federation
  • 7 Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str, Yerevan, 0025, Armenia
Brønsted acid catalyst; Charge-assisted hydrogen-bonded framework; Diels–Alder; Epoxide ring opening; Heterogeneous catalyst
Date of creation
Date of change
Short link

Other records