Perylene Diimide as a Precise Graphene-like Superoxide Dismutase Mimetic

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dc.citation.firstpage2024en_US
dc.citation.issueNumber2en_US
dc.citation.journalTitleACS Nanoen_US
dc.citation.lastpage2032en_US
dc.citation.volumeNumber11en_US
dc.contributor.authorJalilov, Almaz S.en_US
dc.contributor.authorNilewski, Lizanne G.en_US
dc.contributor.authorBerka, Vladimiren_US
dc.contributor.authorZhang, Chenhaoen_US
dc.contributor.authorYakovenko, Andrey A.en_US
dc.contributor.authorWu, Gangen_US
dc.contributor.authorKent, Thomas A.en_US
dc.contributor.authorTsai, Ah-Limen_US
dc.contributor.authorTour, James M.en_US
dc.contributor.orgThe NanoCarbon Centeren_US
dc.date.accessioned2017-03-07T18:24:16Zen_US
dc.date.available2017-03-07T18:24:16Zen_US
dc.date.issued2017en_US
dc.description.abstractHere we show that the active portion of a graphitic nanoparticle can be mimicked by a perylene diimide (PDI) to explain the otherwise elusive biological and electrocatalytic activity of the nanoparticle construct. Development of molecular analogues that mimic the antioxidant properties of oxidized graphenes, in this case the poly(ethylene glycolated) hydrophilic carbon clusters (PEG–HCCs), will afford important insights into the highly efficient activity of PEG–HCCs and their graphitic analogues. PEGylated perylene diimides (PEGn–PDI) serve as well-defined molecular analogues of PEG–HCCs and oxidized graphenes in general, and their antioxidant and superoxide dismutase-like (SOD-like) properties were studied. PEGn–PDIs have two reversible reduction peaks, which are more positive than the oxidation peak of superoxide (O2•–). This is similar to the reduction peak of the HCCs. Thus, as with PEG–HCCs, PEGn–PDIs are also strong single-electron oxidants of O2•–. Furthermore, reduced PEGn–PDI, PEGn–PDI•–, in the presence of protons, was shown to reduce O2•– to H2O2 to complete the catalytic cycle in this SOD analogue. The kinetics of the conversion of O2•– to O2 and H2O2 by PEG8–PDI was measured using freeze-trap EPR experiments to provide a turnover number of 133 s–1; the similarity in kinetics further supports that PEG8–PDI is a true SOD mimetic. Finally, PDIs can be used as catalysts in the electrochemical oxygen reduction reaction in water, which proceeds by a two-electron process with the production of H2O2, mimicking graphene oxide nanoparticles that are otherwise difficult to study spectroscopically.en_US
dc.identifier.citationJalilov, Almaz S., Nilewski, Lizanne G., Berka, Vladimir, et al.. "Perylene Diimide as a Precise Graphene-like Superoxide Dismutase Mimetic." <i>ACS Nano,</i> 11, no. 2 (2017) American Chemical Society: 2024-2032. http://dx.doi.org/10.1021/acsnano.6b08211.en_US
dc.identifier.doihttp://dx.doi.org/10.1021/acsnano.6b08211en_US
dc.identifier.urihttps://hdl.handle.net/1911/94030en_US
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by the American Chemical Society.en_US
dc.subject.keywordelectron paramagnetic resonanceen_US
dc.subject.keywordperylene diimideen_US
dc.subject.keywordradical anionen_US
dc.subject.keywordreactive oxygen speciesen_US
dc.subject.keywordsuperoxide dismutaseen_US
dc.titlePerylene Diimide as a Precise Graphene-like Superoxide Dismutase Mimeticen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpost-printen_US
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