Porphyrin–nanodiamond hybrid materials—active, stable and reusable cyclohexene oxidation catalysts

Bibliographic Details
Main Author: Dias, Lucas D.
Publication Date: 2020
Other Authors: 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.
Format: Article
Language: eng
Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Download full: http://hdl.handle.net/10362/111962
Summary: 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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spelling 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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2024-05-22T17:50:36Zoai:run.unl.pt:10362/111962Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T17:21:40.867986Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
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
status_str 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
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
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collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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