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 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 Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2020, Volume: 16, Pages: 1124-1134 Pages count : 11 DOI: 10.3762/bjoc.16.99

Authors

Kuznetsova Svetlana A ¹ , Gak Alexander S ² , Nelyubina Yulia V ¹ , Larionov Vladimir A ^3,1 , Li Han ⁴ , North Michael ⁴ , Zhereb Vladimir P ⁵ , Smol'yakov Alexander F ¹ , Dmitrienko Artem O ¹ , Medvedev Michael G ^6,1 , Gerasimov Igor S ^6,1 , Saghyan Ashot S ⁷ , Belokon Yuri N ¹

Affiliations

1	Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian Federation,
2	Moscow State University, Faculty of Material Science, Leninskie Gory 1/73, 119991 Moscow, Russian Federation,
3	Department of Inorganic Chemistry, People's Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, 117198 Moscow, 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., 660025 Krasnoyarsk, Russian Federation,
6	N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prospect, 47, 119991 Moscow, Russian Federation and
7	Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str, Yerevan 0025, Armenia

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.

Kuznetsova S.A. , Gak A.S. , Nelyubina Y.V. , Larionov V.A. , Li H. , North M. , Zhereb V.P. , Smol'yakov A.F. , Dmitrienko A.O. , Medvedev M.G. , Gerasimov I.S. , Saghyan A.S. , Belokon Y.N.
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
Beilstein Journal of Organic Chemistry. 2020. V.16. P.1124-1134. DOI: 10.3762/bjoc.16.99 WOS Scopus OpenAlex

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