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-...
| Main Authors: | , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2020-05-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.99 |
| _version_ | 1818406916313841664 |
|---|---|
| author | Svetlana A. Kuznetsova Alexander S. Gak Yulia V. Nelyubina Vladimir A. Larionov Han Li Michael North Vladimir P. Zhereb Alexander F. Smol'yakov Artem O. Dmitrienko Michael G. Medvedev Igor S. Gerasimov Ashot S. Saghyan Yuri N. Belokon |
| author_facet | Svetlana A. Kuznetsova Alexander S. Gak Yulia V. Nelyubina Vladimir A. Larionov Han Li Michael North Vladimir P. Zhereb Alexander F. Smol'yakov Artem O. Dmitrienko Michael G. Medvedev Igor S. Gerasimov Ashot S. Saghyan Yuri N. Belokon |
| author_sort | Svetlana A. Kuznetsova |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-14T09:19:32Z |
| format | Article |
| id | doaj.art-e447d70dd70546169bf17037a67acf93 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T09:19:32Z |
| publishDate | 2020-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e447d70dd70546169bf17037a67acf932022-12-21T23:08:21ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-05-011611124113410.3762/bjoc.16.991860-5397-16-99The 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 catalystsSvetlana A. Kuznetsova0Alexander S. Gak1Yulia V. Nelyubina2Vladimir A. Larionov3Han Li4Michael North5Vladimir P. Zhereb6Alexander F. Smol'yakov7Artem O. Dmitrienko8Michael G. Medvedev9Igor S. Gerasimov10Ashot S. Saghyan11Yuri N. Belokon12Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationMoscow State University, Faculty of Material Science, Leninskie Gory 1/73, 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationGreen Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, YO10 5DD, United KingdomGreen Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, YO10 5DD, United KingdomSiberian Federal University, School of Non-Ferrous Metals and Material Science, 95 Krasnoyarskiy Rabochiy pr., 660025 Krasnoyarsk, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationInstitute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str, Yerevan 0025, ArmeniaNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian FederationThe 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.https://doi.org/10.3762/bjoc.16.99brønsted acid catalystcharge-assisted hydrogen-bonded frameworkdiels–alderepoxide ring openingheterogeneous catalyst |
| spellingShingle | Svetlana A. Kuznetsova Alexander S. Gak Yulia V. Nelyubina Vladimir A. Larionov Han Li Michael North Vladimir P. Zhereb Alexander F. Smol'yakov Artem O. Dmitrienko Michael G. Medvedev Igor S. Gerasimov Ashot S. Saghyan Yuri N. Belokon 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 brønsted acid catalyst charge-assisted hydrogen-bonded framework diels–alder epoxide ring opening heterogeneous catalyst |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | brønsted acid catalyst charge-assisted hydrogen-bonded framework diels–alder epoxide ring opening heterogeneous catalyst |
| url | https://doi.org/10.3762/bjoc.16.99 |
| work_keys_str_mv | AT svetlanaakuznetsova thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT alexandersgak thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT yuliavnelyubina thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT vladimiralarionov thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT hanli thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT michaelnorth thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT vladimirpzhereb thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT alexanderfsmolyakov thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT artemodmitrienko thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT michaelgmedvedev thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT igorsgerasimov thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT ashotssaghyan thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT yurinbelokon thechargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT svetlanaakuznetsova chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT alexandersgak chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT yuliavnelyubina chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT vladimiralarionov chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT hanli chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT michaelnorth chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT vladimirpzhereb chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT alexanderfsmolyakov chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT artemodmitrienko chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT michaelgmedvedev chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT igorsgerasimov chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT ashotssaghyan chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts AT yurinbelokon chargeassistedhydrogenbondedorganicframeworkcahofselfassembledfromtheconjugatedacidoftetrakis4aminophenylmethaneand26naphthalenedisulfonateasanewclassofrecyclablebrønstedacidcatalysts |