Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2020 |
| Outros Autores: | , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
| Texto Completo: | http://hdl.handle.net/10362/111962 |
Resumo: | funded by FCT-Foundation for Science and Technology, I.P., under projects UIDB/00313/2020; PTDC/QUI-OUT/27996/2017 (DUALPI); POCI-01-0145-FEDER-027996; POCI-01-0145-FEDER-016387; UIDB/50006/2020 (Associate Laboratory for Green Chemistry-LAQV); MATIS (CENTRO-010145-FEDER-00014); Base Funding-UIDB/50020/2020 of the Associate Laboratory LSRE-LCM-funded by national funds through FCT/MCTES (PIDDAC); and 5625-DRI-DAAD-2020/21. SACC also acknowledges FCT Investigador FCT program (IF/01381/2013/CP1160/CT0007) and Scientific Employment Stimulus -Institutional Call (CEECINST/00102/2018). The authors also thank Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) for CEPOF 2013/07276-1, and INCT "Basic Optics and Applied to Life Sciences" (FAPESP 2014/50857-8, CNPq 465360/2014-9). A.R.L. Caires acknowledges CAPES-PrInt funding program (grant number 88887.353061/2019-00 and 88881.311921/2018-01). J.G.B. thanks the Dutch Research Council (NWO) for funding as a part of the Open Technology Programme (project number 16361). L.D. Dias thanks FAPESP for the Post-doc grant 2019/13569-8. F.M.S.R. thanks FCT for the PhD grant (PD/BD/114340/2016). |
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Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalystsAllylic oxidationCopper (II) porphyrinNanodiamondsCatalysisPhysical and Theoretical Chemistryfunded by FCT-Foundation for Science and Technology, I.P., under projects UIDB/00313/2020; PTDC/QUI-OUT/27996/2017 (DUALPI); POCI-01-0145-FEDER-027996; POCI-01-0145-FEDER-016387; UIDB/50006/2020 (Associate Laboratory for Green Chemistry-LAQV); MATIS (CENTRO-010145-FEDER-00014); Base Funding-UIDB/50020/2020 of the Associate Laboratory LSRE-LCM-funded by national funds through FCT/MCTES (PIDDAC); and 5625-DRI-DAAD-2020/21. SACC also acknowledges FCT Investigador FCT program (IF/01381/2013/CP1160/CT0007) and Scientific Employment Stimulus -Institutional Call (CEECINST/00102/2018). The authors also thank Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) for CEPOF 2013/07276-1, and INCT "Basic Optics and Applied to Life Sciences" (FAPESP 2014/50857-8, CNPq 465360/2014-9). A.R.L. Caires acknowledges CAPES-PrInt funding program (grant number 88887.353061/2019-00 and 88881.311921/2018-01). J.G.B. thanks the Dutch Research Council (NWO) for funding as a part of the Open Technology Programme (project number 16361). L.D. Dias thanks FAPESP for the Post-doc grant 2019/13569-8. F.M.S.R. thanks FCT for the PhD grant (PD/BD/114340/2016).The quest for active, yet “green” non-toxic catalysts is a continuous challenge. In this work, covalently linked hybrid porphyrin–nanodiamonds were prepared via ipso nitro substitution reaction and characterized by X-ray photoelectron spectroscopy (XPS), fluorescence spectroscopy, infrared spectroscopy (IR) and thermogravimetry-differential scanning calorimetry (TG-DSC). The amine-functionalized nanodiamonds (ND@NH2 ) and 2-nitro-5,10,15,20-tetra(4-trifluoromethylphenyl)porphyrin covalently linked to nanodiamonds (ND@βNH-TPPpCF3 ) were tested using Allium cepa as a plant model, and showed neither phytotoxicity nor cytotoxicity. The hybrid nanodiamond–copper(II)–porphyrin material ND@βNH-TPPpCF3-Cu(II) was also evaluated as a reusable catalyst in cyclohexene allylic oxidation, and displayed a remarkable turnover number (TON) value of ≈265,000, using O2 as green oxidant, in the total absence of sacrificial additives, which is the highest activity ever reported for said allylic oxidation. Additionally, ND@βNH-TPPpCF3-Cu(II) could be easily separated from the reaction mixture by centrifugation, and reused in three consecutive catalytic cycles without major loss of activity.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNDias, Lucas D.Rodrigues, Fábio M. S.Calvete, Mário J. F.Carabineiro, Sónia A. C.Scherer, Marisa D.Caires, Anderson R.L.Buijnsters, Josephus G.Figueiredo, José L.Bagnato, Vanderlei S.Pereira, Mariette M.2021-02-16T23:29:37Z2020-122020-12-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article13application/pdfhttp://hdl.handle.net/10362/111962eng2073-4344PURE: 26879566https://doi.org/10.3390/catal10121402info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-10T15:58:28ZPortal AgregadorONG |
| dc.title.none.fl_str_mv |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| title |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| spellingShingle |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts Dias, Lucas D. Allylic oxidation Copper (II) porphyrin Nanodiamonds Catalysis Physical and Theoretical Chemistry |
| title_short |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| title_full |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| title_fullStr |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| title_full_unstemmed |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| title_sort |
Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts |
| author |
Dias, Lucas D. |
| author_facet |
Dias, Lucas D. Rodrigues, Fábio M. S. Calvete, Mário J. F. Carabineiro, Sónia A. C. Scherer, Marisa D. Caires, Anderson R.L. Buijnsters, Josephus G. Figueiredo, José L. Bagnato, Vanderlei S. Pereira, Mariette M. |
| author_role |
author |
| author2 |
Rodrigues, Fábio M. S. Calvete, Mário J. F. Carabineiro, Sónia A. C. Scherer, Marisa D. Caires, Anderson R.L. Buijnsters, Josephus G. Figueiredo, José L. Bagnato, Vanderlei S. Pereira, Mariette M. |
| author2_role |
author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
LAQV@REQUIMTE DQ - Departamento de Química RUN |
| dc.contributor.author.fl_str_mv |
Dias, Lucas D. Rodrigues, Fábio M. S. Calvete, Mário J. F. Carabineiro, Sónia A. C. Scherer, Marisa D. Caires, Anderson R.L. Buijnsters, Josephus G. Figueiredo, José L. Bagnato, Vanderlei S. Pereira, Mariette M. |
| dc.subject.por.fl_str_mv |
Allylic oxidation Copper (II) porphyrin Nanodiamonds Catalysis Physical and Theoretical Chemistry |
| topic |
Allylic oxidation Copper (II) porphyrin Nanodiamonds Catalysis Physical and Theoretical Chemistry |
| description |
funded by FCT-Foundation for Science and Technology, I.P., under projects UIDB/00313/2020; PTDC/QUI-OUT/27996/2017 (DUALPI); POCI-01-0145-FEDER-027996; POCI-01-0145-FEDER-016387; UIDB/50006/2020 (Associate Laboratory for Green Chemistry-LAQV); MATIS (CENTRO-010145-FEDER-00014); Base Funding-UIDB/50020/2020 of the Associate Laboratory LSRE-LCM-funded by national funds through FCT/MCTES (PIDDAC); and 5625-DRI-DAAD-2020/21. SACC also acknowledges FCT Investigador FCT program (IF/01381/2013/CP1160/CT0007) and Scientific Employment Stimulus -Institutional Call (CEECINST/00102/2018). The authors also thank Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) for CEPOF 2013/07276-1, and INCT "Basic Optics and Applied to Life Sciences" (FAPESP 2014/50857-8, CNPq 465360/2014-9). A.R.L. Caires acknowledges CAPES-PrInt funding program (grant number 88887.353061/2019-00 and 88881.311921/2018-01). J.G.B. thanks the Dutch Research Council (NWO) for funding as a part of the Open Technology Programme (project number 16361). L.D. Dias thanks FAPESP for the Post-doc grant 2019/13569-8. F.M.S.R. thanks FCT for the PhD grant (PD/BD/114340/2016). |
| publishDate |
2020 |
| dc.date.none.fl_str_mv |
2020-12 2020-12-01T00:00:00Z 2021-02-16T23:29:37Z |
| dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
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publishedVersion |
| dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10362/111962 |
| url |
http://hdl.handle.net/10362/111962 |
| dc.language.iso.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
2073-4344 PURE: 26879566 https://doi.org/10.3390/catal10121402 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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13 application/pdf |
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