Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction

Alessandro Mercadante; Vincenzo Campisciano; Anthony Morena; Laura Valentino; Valeria La Parola; Carmela Aprile; Michelangelo Gruttadauria; Francesco Giacalone

doi:10.1002/ejoc.202200497

Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction

Alessandro Mercadante, Vincenzo Campisciano, Anthony Morena, Laura Valentino, Valeria La Parola, Carmela Aprile, Michelangelo Gruttadauria, Francesco Giacalone

Universite de Namur

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7±2.8 nm) whereas a palladium loading of 20.3 wt % has been found by inductively coupled plasma optical emission spectroscopy (ICP-OES). The carbon nanotube-catechol-Pd hybrid was used as catalyst in two C−C coupling reactions, namely Suzuki and Heck reactions, resulting recyclable for at least 9 times in the latter process. During the reuse Pd nanoparticles increase their dimension to 19.3±11.7 nm.

langue originale	Anglais
Numéro d'article	e202200497
journal	European Journal of Organic Chemistry
Volume	2022
Numéro de publication	38
Les DOIs	https://doi.org/10.1002/ejoc.202200497
Etat de la publication	Publié - 13 oct. 2022

Financement

The authors gratefully acknowledge the University of Palermo and the Italian Ministry of Education, University and Research (MIUR) for financial support through PRIN 2017 (projects no. 2017W8KNZW and 2017YJMPZN). Open Access funding provided by Universit\u00E0 degli Studi di Palermo within the CRUI-CARE Agreement. The authors gratefully acknowledge the University of Palermo and the Italian Ministry of Education, University and Research (MIUR) for financial support through PRIN 2017 (projects no. 2017W8KNZW and 2017YJMPZN). Open Access funding provided by Universit\u00E0 degli Studi di Palermo within the CRUI\u2010CARE Agreement.

Bailleurs de fonds	Numéro du bailleur de fonds
Ministero dell’Istruzione, dell’Università e della Ricerca	2017W8KNZW, 2017YJMPZN
Ministero dell’Istruzione, dell’Università e della Ricerca
Università degli Studi di Palermo

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10.1002/ejoc.202200497

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@article{037da226c91845448d279b8bd457d002,

title = "Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction",

abstract = "Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7±2.8 nm) whereas a palladium loading of 20.3 wt % has been found by inductively coupled plasma optical emission spectroscopy (ICP-OES). The carbon nanotube-catechol-Pd hybrid was used as catalyst in two C−C coupling reactions, namely Suzuki and Heck reactions, resulting recyclable for at least 9 times in the latter process. During the reuse Pd nanoparticles increase their dimension to 19.3±11.7 nm.",

keywords = "Carbon nanotubes, C−C coupling reactions, Heterogeneous catalysis, Palladium nanoparticles, Suzuki and Heck reactions",

author = "Alessandro Mercadante and Vincenzo Campisciano and Anthony Morena and Laura Valentino and {La Parola}, Valeria and Carmela Aprile and Michelangelo Gruttadauria and Francesco Giacalone",

note = "Funding Information: The authors gratefully acknowledge the University of Palermo and the Italian Ministry of Education, University and Research (MIUR) for financial support through PRIN 2017 (projects no. 2017W8KNZW and 2017YJMPZN). Open Access funding provided by Universit{\`a} degli Studi di Palermo within the CRUI‐CARE Agreement. Publisher Copyright: {\textcopyright} 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.",

year = "2022",

month = oct,

day = "13",

doi = "10.1002/ejoc.202200497",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction. / Mercadante, Alessandro; Campisciano, Vincenzo; Morena, Anthony et al.
Dans: European Journal of Organic Chemistry, Vol 2022, Numéro 38, e202200497, 13.10.2022.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles

T2 - a Recyclable System for the Heck Reaction

AU - Mercadante, Alessandro

AU - Campisciano, Vincenzo

AU - Morena, Anthony

AU - Valentino, Laura

AU - La Parola, Valeria

AU - Aprile, Carmela

AU - Gruttadauria, Michelangelo

AU - Giacalone, Francesco

N1 - Funding Information: The authors gratefully acknowledge the University of Palermo and the Italian Ministry of Education, University and Research (MIUR) for financial support through PRIN 2017 (projects no. 2017W8KNZW and 2017YJMPZN). Open Access funding provided by Università degli Studi di Palermo within the CRUI‐CARE Agreement. Publisher Copyright: © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.

PY - 2022/10/13

Y1 - 2022/10/13

N2 - Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7±2.8 nm) whereas a palladium loading of 20.3 wt % has been found by inductively coupled plasma optical emission spectroscopy (ICP-OES). The carbon nanotube-catechol-Pd hybrid was used as catalyst in two C−C coupling reactions, namely Suzuki and Heck reactions, resulting recyclable for at least 9 times in the latter process. During the reuse Pd nanoparticles increase their dimension to 19.3±11.7 nm.

AB - Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7±2.8 nm) whereas a palladium loading of 20.3 wt % has been found by inductively coupled plasma optical emission spectroscopy (ICP-OES). The carbon nanotube-catechol-Pd hybrid was used as catalyst in two C−C coupling reactions, namely Suzuki and Heck reactions, resulting recyclable for at least 9 times in the latter process. During the reuse Pd nanoparticles increase their dimension to 19.3±11.7 nm.

KW - Carbon nanotubes

KW - C−C coupling reactions

KW - Heterogeneous catalysis

KW - Palladium nanoparticles

KW - Suzuki and Heck reactions

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U2 - 10.1002/ejoc.202200497

DO - 10.1002/ejoc.202200497

M3 - Article

AN - SCOPUS:85135916707

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 38

M1 - e202200497

ER -

Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction

Résumé

Financement

Accès au document

Autres fichiers et liens

Empreinte digitale

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Physico-chimie et caractérisation (PC2)

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