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

Alexander Gak; Svetlana Kuznetsova; Yulia Nelyubina; Alexander A. Korlyukov; Han Li; Michael North; Vladimir Zhereb; Vladimir Riazanov; Alexander S. Peregudov; Ekaterina Khakina; Nikolai Lobanov; Victor N. Khrustalev; Yuri N. Belokon

doi:10.1021/acs.cgd.1c00838

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

Alexander Gak, Svetlana Kuznetsova, Yulia Nelyubina, Alexander A. Korlyukov, Han Li, Michael North, Vladimir Zhereb, Vladimir Riazanov, Alexander S. Peregudov, Ekaterina Khakina, Nikolai Lobanov, Victor N. Khrustalev, Yuri N. Belokon^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Journal	Crystal Growth and Design
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.cgd.1c00838
Publication status	Published - 30 Sep 2021

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Funding Information:
X-ray diffraction data were collected with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS and the RUDN University Strategic Academic Leadership Program.

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Gak, A., Kuznetsova, S., Nelyubina, Y., Korlyukov, A. A., Li, H., North, M., Zhereb, V., Riazanov, V., Peregudov, A. S., Khakina, E., Lobanov, N., Khrustalev, V. N., & Belokon, Y. N. (2021). Inhibition by Water during Heterogeneous Brønsted Acid Catalysis by Three-Dimensional Crystalline Organic Salts. Crystal Growth and Design, 21(11). https://doi.org/10.1021/acs.cgd.1c00838

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title = "Inhibition by Water during Heterogeneous Br{\o}nsted Acid Catalysis by Three-Dimensional Crystalline Organic Salts",

abstract = "A new self-assembled and self-healing class of metal free, recyclable, heterogeneous Br{\o}nsted 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.",

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note = "Funding Information: X-ray diffraction data were collected with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS and the RUDN University Strategic Academic Leadership Program. Publisher Copyright: {\textcopyright} ",

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AU - Gak, Alexander

AU - Kuznetsova, Svetlana

AU - Nelyubina, Yulia

AU - Korlyukov, Alexander A.

AU - Li, Han

AU - North, Michael

AU - Zhereb, Vladimir

AU - Riazanov, Vladimir

AU - Peregudov, Alexander S.

AU - Khakina, Ekaterina

AU - Lobanov, Nikolai

AU - Khrustalev, Victor N.

AU - Belokon, Yuri N.

N1 - Funding Information: X-ray diffraction data were collected with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS and the RUDN University Strategic Academic Leadership Program. Publisher Copyright: ©

PY - 2021/9/30

Y1 - 2021/9/30

N2 - 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.

AB - 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.

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

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