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Click nanosponge - A novel amine-rich β-cyclodextrin-based crosslinked polymer for heterogeneous catalysis

Machado, Tiago F ; Utzeri, Gianluca LU orcid ; Valente, Artur J M ; Serra, M Elisa Silva and Murtinho, Dina (2024) In Carbohydrate Polymers 326. p.121612-121612
Abstract

Cyclodextrin-based nanosponges are promising materials for heterogeneous catalysis due to their inherent synthetic versatility, tunable porosity and nontoxicity. In this work, a primary amine-rich β-cyclodextrin nanosponge was synthesized via click imine condensation reaction between 1,6-hexamethylamine-functionalized β-cyclodextrin (CDAM) and glutaraldehyde (GLT) to afford CDGLAM, in mild conditions. The crosslinked polymer exhibited a BET surface area of 36.39 m2 g-1, an average pore diameter of 3.09 nm (as assessed by the BJH method), and thermal stability up to 253 °C. CDGLAM was tested as heterogeneous catalyst for the metal-free Henry and Knoevenagel reactions, between aromatic aldehydes and nitromethane or ethyl... (More)

Cyclodextrin-based nanosponges are promising materials for heterogeneous catalysis due to their inherent synthetic versatility, tunable porosity and nontoxicity. In this work, a primary amine-rich β-cyclodextrin nanosponge was synthesized via click imine condensation reaction between 1,6-hexamethylamine-functionalized β-cyclodextrin (CDAM) and glutaraldehyde (GLT) to afford CDGLAM, in mild conditions. The crosslinked polymer exhibited a BET surface area of 36.39 m2 g-1, an average pore diameter of 3.09 nm (as assessed by the BJH method), and thermal stability up to 253 °C. CDGLAM was tested as heterogeneous catalyst for the metal-free Henry and Knoevenagel reactions, between aromatic aldehydes and nitromethane or ethyl cyanoacetate, respectively, affording the products in moderate to very high yields. These results show the ease of preparation of β-CD-based nanosponges from a green chemistry perspective, as well as their potential for future use in catalytic systems.

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author
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publishing date
type
Contribution to journal
publication status
published
subject
in
Carbohydrate Polymers
volume
326
pages
121612 - 121612
publisher
Elsevier
external identifiers
  • scopus:85180780265
  • pmid:38142073
ISSN
0144-8617
DOI
10.1016/j.carbpol.2023.121612
language
English
LU publication?
no
additional info
Copyright © 2023 Elsevier Ltd. All rights reserved.
id
a167b86a-1df3-4409-a725-76985451630f
date added to LUP
2024-03-20 13:44:20
date last changed
2024-04-18 04:04:53
@article{a167b86a-1df3-4409-a725-76985451630f,
  abstract     = {{<p>Cyclodextrin-based nanosponges are promising materials for heterogeneous catalysis due to their inherent synthetic versatility, tunable porosity and nontoxicity. In this work, a primary amine-rich β-cyclodextrin nanosponge was synthesized via click imine condensation reaction between 1,6-hexamethylamine-functionalized β-cyclodextrin (CDAM) and glutaraldehyde (GLT) to afford CDGLAM, in mild conditions. The crosslinked polymer exhibited a BET surface area of 36.39 m2 g<sup>-1</sup>, an average pore diameter of 3.09 nm (as assessed by the BJH method), and thermal stability up to 253 °C. CDGLAM was tested as heterogeneous catalyst for the metal-free Henry and Knoevenagel reactions, between aromatic aldehydes and nitromethane or ethyl cyanoacetate, respectively, affording the products in moderate to very high yields. These results show the ease of preparation of β-CD-based nanosponges from a green chemistry perspective, as well as their potential for future use in catalytic systems.</p>}},
  author       = {{Machado, Tiago F and Utzeri, Gianluca and Valente, Artur J M and Serra, M Elisa Silva and Murtinho, Dina}},
  issn         = {{0144-8617}},
  language     = {{eng}},
  month        = {{02}},
  pages        = {{121612--121612}},
  publisher    = {{Elsevier}},
  series       = {{Carbohydrate Polymers}},
  title        = {{Click nanosponge - A novel amine-rich β-cyclodextrin-based crosslinked polymer for heterogeneous catalysis}},
  url          = {{http://dx.doi.org/10.1016/j.carbpol.2023.121612}},
  doi          = {{10.1016/j.carbpol.2023.121612}},
  volume       = {{326}},
  year         = {{2024}},
}