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The nanocatalyst was fabricated by the covalent immobilization of 4-aminoantipyrine onto an amine-functionalized graphene oxide nanosupport followed by its metallation with copper acetate. Structural analysis by transmission electron microscopy, scanning electron microscopy, X-ray photoelectron spectroscopy (XPS), and X-ray diffraction demonstrates that the two-dimensional sheet-like structure of graphene oxide is maintained even after the chemical modifications, whereas XPS revealed crucial information related to elemental composition and surface electronic states of the metal present in the catalyst. Apart from this, Fourier transform infrared spectroscopy helped in identifying the degree of oxidation and the presence of oxygenated groups in graphene oxide nanocomposites. As a heterogeneous catalyst, this graphene oxide-supported copper complex showed moderate to good catalytic activity in the C(sp3)\u2013H bond activation\/amination of a variety of substrates. This superior catalytic performance originated from the unique 2-dimensional structure of graphene oxide-based material which provided space between graphitic overlayers due to appropriate positioning of metal on their basal planes, decreasing the diffusion resistances of reactant surfaces, thus making it function as a nanoreactor. More importantly, this nanomaterial could be recovered easily and reused repeatedly by simple washing without chemical treatment with no appreciable loss in its catalytic activity, showing good potential for increasing the overall turnover number of this synthetically useful catalyst.<\/jats:p>","DOI":"10.1021\/acsomega.8b02902","type":"journal-article","created":{"date-parts":[[2019,2,13]],"date-time":"2019-02-13T12:43:32Z","timestamp":1550061812000},"page":"3146-3158","source":"Crossref","is-referenced-by-count":21,"title":["Design and Exploration of Catalytic Activity of Two-Dimensional\nSurface-Engineered Graphene Oxide Nanosheets in the Transannulation\nof N-Heterocyclic Aldehydes or Ketones with Alkylamines"],"prefix":"10.1021","volume":"4","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4281-876X","authenticated-orcid":true,"given":"Rakesh K.","family":"Sharma","sequence":"first","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aditi","family":"Sharma","sequence":"additional","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shivani","family":"Sharma","sequence":"additional","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sriparna","family":"Dutta","sequence":"additional","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sneha","family":"Yadav","sequence":"additional","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bhavya","family":"Arora","sequence":"additional","affiliation":[{"name":"University of Delhi , , ,","place":["New Delhi, India, 110007"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,2,12]]},"reference":[{"key":"2026090209095253200_cit1","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1021\/ja210660g","article-title":"Highly efficient\nsyntheses of azetidines, pyrrolidines, and indolines via palladium\ncatalyzed intramolecular amination of C (sp3)\u2013H\nand C (sp2)\u2013H bonds at \u03b3 and \u03b4 positions","volume":"134","author":"He","year":"2011","journal-title":"J. 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Organomet. Chem."},{"key":"2026090209095253200_cit71","doi-asserted-by":"publisher","first-page":"1561","DOI":"10.1039\/c3nj00099k","article-title":"Immobilized Cu(ii) and Co(ii) salen\ncomplexes on graphene oxide and their catalytic activity for aerobic\nepoxidation of styrene","volume":"37","author":"Li","year":"2013","journal-title":"New J. Chem."},{"key":"2026090209095253200_cit72","doi-asserted-by":"publisher","first-page":"4232","DOI":"10.1021\/ie500017z","article-title":"Catalytic epoxidation of olefins with graphene oxide supported copper\n(Salen) complex","volume":"53","author":"Zhao","year":"2014","journal-title":"Ind. Eng. Chem. Res."},{"key":"2026090209095253200_cit73","doi-asserted-by":"publisher","first-page":"8054","DOI":"10.1039\/c3dt53421a","article-title":"Grafting\nof a rhenium-oxo complex on Schiff base functionalized graphene oxide:\nan efficient catalyst for the oxidation of amines","volume":"43","author":"Khatri","year":"2014","journal-title":"Dalton Trans."},{"key":"2026090209095253200_cit74","doi-asserted-by":"publisher","first-page":"6905","DOI":"10.1039\/c3tc31124d","article-title":"Raman spectroscopy for the study of reduction mechanisms\nand optimization of conductivity in graphene oxide thin films","volume":"1","author":"Di\u0301ez-Betriu","year":"2013","journal-title":"J. Mater. Chem. C"},{"key":"2026090209095253200_cit75","doi-asserted-by":"publisher","first-page":"20489","DOI":"10.1021\/acs.jpcc.7b06236","article-title":"Evolution\nof the Raman Spectrum with the Chemical Composition of Graphene Oxide","volume":"121","author":"Lo\u0301pez-Di\u0301az","year":"2017","journal-title":"J. Phys. Chem. C"},{"key":"2026090209095253200_cit76","doi-asserted-by":"publisher","first-page":"3092","DOI":"10.1021\/am100597d","article-title":"Preparation of covalently functionalized\ngraphene using residual oxygen-containing functional groups","volume":"2","author":"Hsiao","year":"2010","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"2026090209095253200_cit77","doi-asserted-by":"publisher","first-page":"2962","DOI":"10.1002\/1521-3773(20020816)41:16&lt;2962::aid-anie2962&gt;3.0.co;2-6","article-title":"Copper-Catalyzed\nOxidative Heterocyclization by Atmospheric Oxygen","volume":"41","author":"Bluhm","year":"2002","journal-title":"Angew. Chem., Int. 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