Regioselective Plasmon-Driven Decarboxylation of Mercaptobenzoic Acids Triggered by Distinct Reactive Oxygen Species

The non-radiative decay of surface plasmon resonance (SPR) in plasmonic metal nanoparticles (NPs) opens up unique hot-carrier-driven chemical transformation mechanisms. Here, the hot-carrier generation of reactive oxygen species was demonstrated to trigger the regioselective plasmon-driven decarboxy...

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Published inACS catalysis Vol. 12; no. 23; pp. 14619 - 14628
Main Authors dos Santos Lopes, Douglas, dos Santos Abreu, Dieric, Ando, Rômulo Augusto, Corio, Paola
Format Journal Article
LanguageEnglish
Published American Chemical Society 02.12.2022
Subjects
regioselectivity
decarboxylation
hot carriers
reactive oxygen species
surface plasmon
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Abstract The non-radiative decay of surface plasmon resonance (SPR) in plasmonic metal nanoparticles (NPs) opens up unique hot-carrier-driven chemical transformation mechanisms. Here, the hot-carrier generation of reactive oxygen species was demonstrated to trigger the regioselective plasmon-driven decarboxylation of mercaptobenzoic acid (MBA) isomers over Ag (AgNPs) and Au nanoparticles (AuNPs). Controlled catalytic experiments indicated that the catalytic C–C bond cleavage over AgNPs and AuNPs is primarily initiated by photogenerated singlet oxygen (1O2) and hydroxyl radical (•OH), respectively. Energetic hot electrons on AgNPs can successfully generate 1O2 from 3O2 via Dexter energy transfer, while hot holes generated under the Fermi level of AuNPs have sufficient energy to oxidize OH– and promote the formation of reactive •OH. The catalytic activity trend was evaluated considering the known ortho-substituent effect. The data discussed herein shed light on how the intrinsic differences in electronic energy levels and metal–molecule interactions precisely tune the regioselectivity of plasmon-driven transformations and may guide the rational design of plasmonic catalysts for distinct desired reactions.
AbstractList The non-radiative decay of surface plasmon resonance (SPR) in plasmonic metal nanoparticles (NPs) opens up unique hot-carrier-driven chemical transformation mechanisms. Here, the hot-carrier generation of reactive oxygen species was demonstrated to trigger the regioselective plasmon-driven decarboxylation of mercaptobenzoic acid (MBA) isomers over Ag (AgNPs) and Au nanoparticles (AuNPs). Controlled catalytic experiments indicated that the catalytic C–C bond cleavage over AgNPs and AuNPs is primarily initiated by photogenerated singlet oxygen (1O2) and hydroxyl radical (•OH), respectively. Energetic hot electrons on AgNPs can successfully generate 1O2 from 3O2 via Dexter energy transfer, while hot holes generated under the Fermi level of AuNPs have sufficient energy to oxidize OH– and promote the formation of reactive •OH. The catalytic activity trend was evaluated considering the known ortho-substituent effect. The data discussed herein shed light on how the intrinsic differences in electronic energy levels and metal–molecule interactions precisely tune the regioselectivity of plasmon-driven transformations and may guide the rational design of plasmonic catalysts for distinct desired reactions.
Author dos Santos Abreu, Dieric
dos Santos Lopes, Douglas
Corio, Paola
Ando, Rômulo Augusto
AuthorAffiliation Federal University of Ceara
Department of Fundamental Chemistry, Institute of Chemistry
Department of Analytical Chemistry and Physical Chemistry
AuthorAffiliation_xml – name: Department of Analytical Chemistry and Physical Chemistry
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  givenname: Douglas
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  surname: dos Santos Lopes
  fullname: dos Santos Lopes, Douglas
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  givenname: Dieric
  surname: dos Santos Abreu
  fullname: dos Santos Abreu, Dieric
  organization: Federal University of Ceara
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  givenname: Rômulo Augusto
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  surname: Ando
  fullname: Ando, Rômulo Augusto
  organization: Department of Fundamental Chemistry, Institute of Chemistry
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  givenname: Paola
  orcidid: 0000-0002-0010-5131
  surname: Corio
  fullname: Corio, Paola
  email: paola@iq.usp.br
  organization: Department of Fundamental Chemistry, Institute of Chemistry
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Keywords regioselectivity
decarboxylation
hot carriers
reactive oxygen species
surface plasmon
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Snippet The non-radiative decay of surface plasmon resonance (SPR) in plasmonic metal nanoparticles (NPs) opens up unique hot-carrier-driven chemical transformation...
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Title Regioselective Plasmon-Driven Decarboxylation of Mercaptobenzoic Acids Triggered by Distinct Reactive Oxygen Species
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