Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids
- Autores
- Martin, Maria Guadalupe; Lazaro Martinez, Juan Manuel; Martín, Sandra Elizabeth; Uberman, Paula Marina; Buden, Maria Eugenia
- Año de publicación
- 2023
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2-carboxylic acid (AQ−COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT-IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ−COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h−1. Using 2-propanol as solvent at room temperature, the visible light photocatalysis produced H2O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions.
Fil: Martin, Maria Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
Fil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina - Materia
-
AEROBIC HYDROXYLATION
ANTHRAQUINONE
CATALYSIS
HETEROGENEOUS PHOTOCATALYST
HYDROGEN ATOM TRANSFER - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/226769
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Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic AcidsMartin, Maria GuadalupeLazaro Martinez, Juan ManuelMartín, Sandra ElizabethUberman, Paula MarinaBuden, Maria EugeniaAEROBIC HYDROXYLATIONANTHRAQUINONECATALYSISHETEROGENEOUS PHOTOCATALYSTHYDROGEN ATOM TRANSFERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2-carboxylic acid (AQ−COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT-IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ−COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h−1. Using 2-propanol as solvent at room temperature, the visible light photocatalysis produced H2O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions.Fil: Martin, Maria Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; ArgentinaFil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaWiley VCH Verlag2023-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/226769Martin, Maria Guadalupe; Lazaro Martinez, Juan Manuel; Martín, Sandra Elizabeth; Uberman, Paula Marina; Buden, Maria Eugenia; Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids; Wiley VCH Verlag; Chemistry- A European Journal; 12-2023; 1-140947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202303382info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.202303382info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:23:20Zoai:ri.conicet.gov.ar:11336/226769instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:23:20.623CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
title |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
spellingShingle |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids Martin, Maria Guadalupe AEROBIC HYDROXYLATION ANTHRAQUINONE CATALYSIS HETEROGENEOUS PHOTOCATALYST HYDROGEN ATOM TRANSFER |
title_short |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
title_full |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
title_fullStr |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
title_full_unstemmed |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
title_sort |
Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids |
dc.creator.none.fl_str_mv |
Martin, Maria Guadalupe Lazaro Martinez, Juan Manuel Martín, Sandra Elizabeth Uberman, Paula Marina Buden, Maria Eugenia |
author |
Martin, Maria Guadalupe |
author_facet |
Martin, Maria Guadalupe Lazaro Martinez, Juan Manuel Martín, Sandra Elizabeth Uberman, Paula Marina Buden, Maria Eugenia |
author_role |
author |
author2 |
Lazaro Martinez, Juan Manuel Martín, Sandra Elizabeth Uberman, Paula Marina Buden, Maria Eugenia |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
AEROBIC HYDROXYLATION ANTHRAQUINONE CATALYSIS HETEROGENEOUS PHOTOCATALYST HYDROGEN ATOM TRANSFER |
topic |
AEROBIC HYDROXYLATION ANTHRAQUINONE CATALYSIS HETEROGENEOUS PHOTOCATALYST HYDROGEN ATOM TRANSFER |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2-carboxylic acid (AQ−COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT-IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ−COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h−1. Using 2-propanol as solvent at room temperature, the visible light photocatalysis produced H2O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions. Fil: Martin, Maria Guadalupe. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Lazaro Martinez, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina Fil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina Fil: Buden, Maria Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina |
description |
In this work, the synthesis and characterization of a heterogeneous photocatalyst based on spherical silica nanoparticles superficially modified with anthraquinone 2-carboxylic acid (AQ−COOH) are presented. The nanomaterial was characterized by TEM, SEM, FT-IR, diffuse reflectance, fluorescence, NMR, DLS, XRD and XPS. These analyses confirm the covalent linking of AQ−COOH with the NH2 functionality in the nanomaterial and, more importantly, the photocatalyst retains its photophysical properties once bound. The heterogeneous photocatalyst was successfully employed in the aerobic hydroxylation of arylboronic acids to phenols under sustainable reaction conditions. Phenols were obtained in high yields (up to 100 %) with low catalyst loading (3.5 mol %), reaching TOF values of 3.7 h−1. Using 2-propanol as solvent at room temperature, the visible light photocatalysis produced H2O2 as a key intermediate to promote the aerobic hydroxylation of arylboronic acids. The heterogeneous photocatalyst was reused at least 5 times, without modification of the nanomaterial structure and morphology. This simple heterogeneous system showed great catalytic activity under sustainable reaction conditions. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-12 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/226769 Martin, Maria Guadalupe; Lazaro Martinez, Juan Manuel; Martín, Sandra Elizabeth; Uberman, Paula Marina; Buden, Maria Eugenia; Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids; Wiley VCH Verlag; Chemistry- A European Journal; 12-2023; 1-14 0947-6539 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/226769 |
identifier_str_mv |
Martin, Maria Guadalupe; Lazaro Martinez, Juan Manuel; Martín, Sandra Elizabeth; Uberman, Paula Marina; Buden, Maria Eugenia; Anthraquinone‐Modified Silica Nanoparticles as Heterogeneous Photocatalyst for the Oxidative Hydroxylation of Arylboronic Acids; Wiley VCH Verlag; Chemistry- A European Journal; 12-2023; 1-14 0947-6539 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202303382 info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.202303382 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Wiley VCH Verlag |
publisher.none.fl_str_mv |
Wiley VCH Verlag |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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1846082641927864320 |
score |
13.22299 |