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 Bronsted acid catalysts | Научно-инновационный портал СФУ

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 Bronsted acid catalysts

Тип публикации: статья из журнала

Год издания: 2020

Ключевые слова: brønsted acid catalyst, charge-assisted hydrogen-bonded framework, diels–alder, epoxide ring opening, heterogeneous catalyst

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 H-1 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 Bronsted 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. 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.

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Издание

Журнал: Beilstein journal of organic chemistry

Выпуск журнала: Vol. 16

Номера страниц: 1124-1134

ISSN журнала: 18605397

Место издания: Frankfurt am Main

Издатель: Beilstein-institut

Авторы

  • Kuznetsova Svetlana A.
  • Gak Alexander S.
  • Nelyubina Yulia V.
  • Larionov Vladimir A. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; Peoples Friendship Univ Russia, RUDN Univ, Dept Inorgan Chem, Miklukho Maklaya St 6, Moscow 117198, Russia)
  • Li Han (Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England)
  • North Michael (Univ York, Green Chem Ctr Excellence, Dept Chem, Heslington YO10 5DD, England)
  • Zhereb Vladimir P. (Siberian Fed Univ, Sch Nonferrous Met & Mat Sci, 95 Krasnoyarskiy Rabochiy Pr, Krasnoyarsk 660025, Russia)
  • Smol'yakov Alexander F. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)
  • Dmitrienko Artem O. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)
  • Medvedev Michael G. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; ND Zelinsky Inst Organ Chem RAS, Leninsky Prospect 47, Moscow 119991, Russia)
  • Gerasimov Igor S. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia; ND Zelinsky Inst Organ Chem RAS, Leninsky Prospect 47, Moscow 119991, Russia)
  • Saghyan Ashot S. (Yerevan State Univ, Inst Pharm, 1 Alex Manoogian Str, Yerevan 0025, Armenia )
  • Belokon Yuri N. (Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Vavilov St 28, Moscow 119991, Russia)

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