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Salen-decorated periodic mesoporous organosilica : from metal-assisted epoxidation to metal-free CO2 insertion

Mahdieh Haghighat (UGent) , Karen Leus (UGent) , Farhad Shirini and Pascal Van Der Voort (UGent)
(2021) CHEMISTRY-AN ASIAN JOURNAL. 16(15). p.2126-2135
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Abstract
We clicked a salen ligand onto a thiol-ethane bridged periodic mesoporous organosilica (Salen-PMO) using a photo-initiated thiol-ene click reaction. This process resulted in a covalently bonded salen ligand on the PMO material. The final BET surface area amounts 511 m(2)/g and the pore size diameter is approximately 7 nm. The functionalized PMO material showed an excellent carbon dioxide uptake capacity of 1.29 mmol/g at 273 K and 1 bar. More importantly, by coordinating a MoO22+ complex onto the Salen-PMO material, we obtained a heterogeneous catalyst with a good catalytic performance for the epoxidation of cyclohexene. The catalyst was highly reusable, as no decrease in its activity was observed for at least four runs (99% conversion). Finally, the metal-free Salen-PMO showed an exceptional catalytic performance in the cycloaddition of CO2 to epoxides. The obtained results clearly demonstrate the versatility of the Salen-PMO material not only as metal-free catalyst but also as a support material to anchor metal complexes for specific catalytic applications. With the same catalytic platform, we were able to firstly create epoxides out of alkenes, and subsequently turn these epoxides into cyclic carbonates, consuming CO2.
Keywords
PMO, heterogeneous catalysis, metal free catalysis, salen, Cyclic carbonate, Carbon dioxide, Epoxidation, Salen ligand, Thiol-ene click reaction, Metal-free catalyst, SCHIFF-BASE LIGANDS, EFFICIENT CATALYSTS, CYCLIC CARBONATES, HIGHLY EFFICIENT, BUILDING-BLOCK, ORGANIC GROUPS, COMPLEXES, EPOXIDES, MOLYBDENUM, DIOXIDE

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Citation

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MLA
Haghighat, Mahdieh, et al. “Salen-Decorated Periodic Mesoporous Organosilica : From Metal-Assisted Epoxidation to Metal-Free CO2 Insertion.” CHEMISTRY-AN ASIAN JOURNAL, vol. 16, no. 15, 2021, pp. 2126–35, doi:10.1002/asia.202100524.
APA
Haghighat, M., Leus, K., Shirini, F., & Van Der Voort, P. (2021). Salen-decorated periodic mesoporous organosilica : from metal-assisted epoxidation to metal-free CO2 insertion. CHEMISTRY-AN ASIAN JOURNAL, 16(15), 2126–2135. https://doi.org/10.1002/asia.202100524
Chicago author-date
Haghighat, Mahdieh, Karen Leus, Farhad Shirini, and Pascal Van Der Voort. 2021. “Salen-Decorated Periodic Mesoporous Organosilica : From Metal-Assisted Epoxidation to Metal-Free CO2 Insertion.” CHEMISTRY-AN ASIAN JOURNAL 16 (15): 2126–35. https://doi.org/10.1002/asia.202100524.
Chicago author-date (all authors)
Haghighat, Mahdieh, Karen Leus, Farhad Shirini, and Pascal Van Der Voort. 2021. “Salen-Decorated Periodic Mesoporous Organosilica : From Metal-Assisted Epoxidation to Metal-Free CO2 Insertion.” CHEMISTRY-AN ASIAN JOURNAL 16 (15): 2126–2135. doi:10.1002/asia.202100524.
Vancouver
1.
Haghighat M, Leus K, Shirini F, Van Der Voort P. Salen-decorated periodic mesoporous organosilica : from metal-assisted epoxidation to metal-free CO2 insertion. CHEMISTRY-AN ASIAN JOURNAL. 2021;16(15):2126–35.
IEEE
[1]
M. Haghighat, K. Leus, F. Shirini, and P. Van Der Voort, “Salen-decorated periodic mesoporous organosilica : from metal-assisted epoxidation to metal-free CO2 insertion,” CHEMISTRY-AN ASIAN JOURNAL, vol. 16, no. 15, pp. 2126–2135, 2021.
@article{8714631,
  abstract     = {{We clicked a salen ligand onto a thiol-ethane bridged periodic mesoporous organosilica (Salen-PMO) using a photo-initiated thiol-ene click reaction. This process resulted in a covalently bonded salen ligand on the PMO material. The final BET surface area amounts 511 m(2)/g and the pore size diameter is approximately 7 nm. The functionalized PMO material showed an excellent carbon dioxide uptake capacity of 1.29 mmol/g at 273 K and 1 bar. More importantly, by coordinating a MoO22+ complex onto the Salen-PMO material, we obtained a heterogeneous catalyst with a good catalytic performance for the epoxidation of cyclohexene. The catalyst was highly reusable, as no decrease in its activity was observed for at least four runs (99% conversion). Finally, the metal-free Salen-PMO showed an exceptional catalytic performance in the cycloaddition of CO2 to epoxides. The obtained results clearly demonstrate the versatility of the Salen-PMO material not only as metal-free catalyst but also as a support material to anchor metal complexes for specific catalytic applications. With the same catalytic platform, we were able to firstly create epoxides out of alkenes, and subsequently turn these epoxides into cyclic carbonates, consuming CO2.}},
  author       = {{Haghighat, Mahdieh and Leus, Karen and Shirini, Farhad and Van Der Voort, Pascal}},
  issn         = {{1861-4728}},
  journal      = {{CHEMISTRY-AN ASIAN JOURNAL}},
  keywords     = {{PMO,heterogeneous catalysis,metal free catalysis,salen,Cyclic carbonate,Carbon dioxide,Epoxidation,Salen ligand,Thiol-ene click reaction,Metal-free catalyst,SCHIFF-BASE LIGANDS,EFFICIENT CATALYSTS,CYCLIC CARBONATES,HIGHLY EFFICIENT,BUILDING-BLOCK,ORGANIC GROUPS,COMPLEXES,EPOXIDES,MOLYBDENUM,DIOXIDE}},
  language     = {{eng}},
  number       = {{15}},
  pages        = {{2126--2135}},
  title        = {{Salen-decorated periodic mesoporous organosilica : from metal-assisted epoxidation to metal-free CO2 insertion}},
  url          = {{http://doi.org/10.1002/asia.202100524}},
  volume       = {{16}},
  year         = {{2021}},
}
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