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

Kuznetsova, S.A.; Gak, A.S.; Nelyubina, Y.V.; Larionov, V.A.; Han, L.; North, M.; Zhereb, V.P.; Smolyakov, A.F.; Dmitrienko, A.O.; Medvedev, M.G.; Gerasimov, I.S.; Saghyan, A.S.; Belokon, Y.N.

Авторы: Kuznetsova Svetlana A., Gak Alexander S., Nelyubina Yulia V., Larionov Vladimir A., Han Li, North Michael, Zhereb Vladimir P., Smolyakov Alexander F., Dmitrienko Artem O., Medvedev Michael G., Gerasimov Igor S., Saghyan Ashot S., Belokon Yuri N.
Журнал: Beilstein Journal of Organic Chemistry
Том: 16
Год издания: 2020
Издательство: Beilstein-Institut
Местоположение издательства: Germany
Первая страница: 1124
Последняя страница: 1134
DOI: 10.3762/bjoc.16.99
Аннотация: 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.
Добавил в систему: Ларионов Владимир Анатольевич

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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 catalystsстатья

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