{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,13]],"date-time":"2026-01-13T05:30:21Z","timestamp":1768282221027,"version":"3.49.0"},"reference-count":60,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2020,12,1]],"date-time":"2020-12-01T00:00:00Z","timestamp":1606780800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo (FAPESP)","award":["CEPOF 2013\/07276-1, and INCT \u201cBasic Optics and Applied to Life Sciences\u201d (FAPESP 2014\/50857-8, CNPq 465360\/2014-9)."],"award-info":[{"award-number":["CEPOF 2013\/07276-1, and INCT \u201cBasic Optics and Applied to Life Sciences\u201d (FAPESP 2014\/50857-8, CNPq 465360\/2014-9)."]}]},{"name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo (FAPESP)","award":["Post-doc grant 2019\/13569-8."],"award-info":[{"award-number":["Post-doc grant 2019\/13569-8."]}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["projects UIDB\/00313\/2020, PTDC\/QUI-OUT\/27996\/2017 (DUALPI), POCI-01-0145- FEDER-027996, POCI-01\u20130145-FEDER-016387, UIDB\/50006\/2020 (Associate Laboratory for Green Chemistry - LAQV), MATIS (CENTRO-010145-FEDER-00014), Base Funding \u2013 UIDB\/50020\/2020 of the"],"award-info":[{"award-number":["projects UIDB\/00313\/2020, PTDC\/QUI-OUT\/27996\/2017 (DUALPI), POCI-01-0145- FEDER-027996, POCI-01\u20130145-FEDER-016387, UIDB\/50006\/2020 (Associate Laboratory for Green Chemistry - LAQV), MATIS (CENTRO-010145-FEDER-00014), Base Funding \u2013 UIDB\/50020\/2020 of the"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["PhD grant (PD\/BD\/114340\/2016)."],"award-info":[{"award-number":["PhD grant (PD\/BD\/114340\/2016)."]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"CAPES-PrInt funding program","award":["Grant no. 88887.353061\/2019-00 and 88881.311921\/2018-01)"],"award-info":[{"award-number":["Grant no. 88887.353061\/2019-00 and 88881.311921\/2018-01)"]}]},{"name":"Dutch Research Council (NWO)","award":["Open Technology Programme (project no. 16361)."],"award-info":[{"award-number":["Open Technology Programme (project no. 16361)."]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Catalysts"],"abstract":"<jats:p>The quest for active, yet \u201cgreen\u201d non-toxic catalysts is a continuous challenge. In this work, covalently linked hybrid porphyrin\u2013nanodiamonds 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@\u03b2NH-TPPpCF3) were tested using Allium cepa as a plant model, and showed neither phytotoxicity nor cytotoxicity. The hybrid nanodiamond\u2013copper(II)\u2013porphyrin material ND@\u03b2NH-TPPpCF3-Cu(II) was also evaluated as a reusable catalyst in cyclohexene allylic oxidation, and displayed a remarkable turnover number (TON) value of \u2248265,000, 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@\u03b2NH-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.<\/jats:p>","DOI":"10.3390\/catal10121402","type":"journal-article","created":{"date-parts":[[2020,12,1]],"date-time":"2020-12-01T13:08:51Z","timestamp":1606828131000},"page":"1402","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Porphyrin\u2013Nanodiamond Hybrid Materials\u2014Active, Stable and Reusable Cyclohexene Oxidation Catalysts"],"prefix":"10.3390","volume":"10","author":[{"given":"Lucas D.","family":"Dias","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, CQC, Universidade de Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"},{"name":"S\u00e3o Carlos Institute of Physics, University of S\u00e3o Paulo, S\u00e3o Carlos 13566-590, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1085-2720","authenticated-orcid":false,"given":"F\u00e1bio M. S.","family":"Rodrigues","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, CQC, Universidade de Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2094-4781","authenticated-orcid":false,"given":"M\u00e1rio J. F.","family":"Calvete","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, CQC, Universidade de Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9913-4671","authenticated-orcid":false,"given":"S\u00f3nia A. C.","family":"Carabineiro","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Materials, Associate Laboratory LSRE-LCM, Faculty of Engineering, University of Porto, Rua Dr. Roberto Frias s\/n, 4200-465 Porto, Portugal"},{"name":"LAQV-REQUIMTE, Department of Chemistry, NOVA School of Science and Technology, Universidade NOVA de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal"}]},{"given":"Marisa D.","family":"Scherer","sequence":"additional","affiliation":[{"name":"Grupo de \u00d3ptica e Fot\u00f4nica, Universidade Federal de Mato Grosso do Sul, CP 549, Campo Grande 79070-900, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2602-9480","authenticated-orcid":false,"given":"Anderson R. L.","family":"Caires","sequence":"additional","affiliation":[{"name":"Grupo de \u00d3ptica e Fot\u00f4nica, Universidade Federal de Mato Grosso do Sul, CP 549, Campo Grande 79070-900, Brazil"},{"name":"School of Life Sciences, University of Essex, Colchester CO4 3SQ, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5440-8154","authenticated-orcid":false,"given":"Josephus G.","family":"Buijnsters","sequence":"additional","affiliation":[{"name":"Department of Precision and Microsystems Engineering, Micro and Nano Engineering, Delft University of Technology, 2628 CD Delft, The Netherlands"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0395-8199","authenticated-orcid":false,"given":"Jos\u00e9 L.","family":"Figueiredo","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Materials, Associate Laboratory LSRE-LCM, Faculty of Engineering, University of Porto, Rua Dr. Roberto Frias s\/n, 4200-465 Porto, Portugal"}]},{"given":"Vanderlei S.","family":"Bagnato","sequence":"additional","affiliation":[{"name":"S\u00e3o Carlos Institute of Physics, University of S\u00e3o Paulo, S\u00e3o Carlos 13566-590, Brazil"},{"name":"Hagler Fellow, Department of Biomedical Engineering, Texas A&amp;M University\u2013College Station Texas, 400 Bizzell St, College Station, TX 77843, USA"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4958-7677","authenticated-orcid":false,"given":"Mariette M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, CQC, Universidade de Coimbra, Rua Larga, 3004-535 Coimbra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2020,12,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1134\/1.1711431","article-title":"On the history of the discovery of nanodiamond synthesis","volume":"46","author":"Danilenko","year":"2004","journal-title":"Phys. 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