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Sonogashira Synthesis of New Porous Aromatic Framework-Entrapped Palladium Nanoparticles as Heterogeneous Catalysts for Suzuki–Miyaura Cross-Coupling

  • Lidia Căta
    Lidia Căta
    Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Babes-Bolyai University, 11, Arany Janos str., Cluj-Napoca, 400028 Cluj, Romania
    More by Lidia Căta
  • Natalia Terenti
    Natalia Terenti
    Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Babes-Bolyai University, 11, Arany Janos str., Cluj-Napoca, 400028 Cluj, Romania
  • Cristina Cociug
    Cristina Cociug
    Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Babes-Bolyai University, 11, Arany Janos str., Cluj-Napoca, 400028 Cluj, Romania
  • Niculina Daniela Hădade*
    Niculina Daniela Hădade
    Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Babes-Bolyai University, 11, Arany Janos str., Cluj-Napoca, 400028 Cluj, Romania
    *Email: [email protected]
  • Ion Grosu*
    Ion Grosu
    Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Babes-Bolyai University, 11, Arany Janos str., Cluj-Napoca, 400028 Cluj, Romania
    *Email: [email protected]
    More by Ion Grosu
  • Cristina Bucur
    Cristina Bucur
    National Institute of Materials Physics, 405 Atomiştilor Str., Măgurele 077125, Ilfov, Romania
  • Bogdan Cojocaru
    Bogdan Cojocaru
    Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Regina Elisabeta Blvd., no. 4-12, Bucharest 030016, Romania
  • Vasile I. Parvulescu*
    Vasile I. Parvulescu
    Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Regina Elisabeta Blvd., no. 4-12, Bucharest 030016, Romania
    *Email: [email protected]
  • Michal Mazur
    Michal Mazur
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, Prague 128 43, Czech Republic
    More by Michal Mazur
  • , and 
  • Jiří Čejka*
    Jiří Čejka
    Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, Prague 128 43, Czech Republic
    *Email: [email protected]
Cite this: ACS Appl. Mater. Interfaces 2022, 14, 8, 10428–10437
Publication Date (Web):February 16, 2022
https://doi.org/10.1021/acsami.1c24429
Copyright © 2022 American Chemical Society

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    Abstract

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    Palladium nanoparticles entrapped in porous aromatic frameworks (PAFs) or covalent organic frameworks may promote heterogeneous catalytic reactions. However, preparing such materials as active nanocatalysts usually requires additional steps for palladium entrapment and reduction. This paper reports as a new approach, a simple procedure leading to the self-entrapment of Pd nanoparticles within the PAF structure. Thus, the selected Sonogashira synthesis affords PAF-entrapped Pd nanoparticles that can catalyze the C–C Suzuki–Miyaura cross-coupling reactions. Following this new concept, PAFs were synthesized via Sonogashira cross-coupling of the tetraiodurated derivative of tetraphenyladamantane or spiro-9,9′-bifluorene with 1,6-diethynylpyrene, then characterized them using powder X-ray diffraction, diffuse reflectance infrared Fourier transform spectroscopy, X-ray photoelectron spectroscopy, high-resolution scanning transmission electron microscopy, and textural properties (i.e., adsorption–desorption isotherms). The PAF-entrapped Pd nanocatalysts showed high catalytic activity in Suzuki–Miyaura coupling reactions (demonstrated by preserving the turnover frequency values) and stability (demonstrated by palladium leaching and recycling experiments). This new approach presents a new class of PAFs with unique structural, topological, and compositional complexities as entrapped metal nanocatalysts or for other diverse applications.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsami.1c24429.

    • Adsorption–desorption isotherms; DRIFT, XPS, STEM, FT-IR, and Raman data; and 1H NMR spectra of all compounds (PDF)

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    Cited By

    This article is cited by 8 publications.

    1. Leila Mohammadi, Mohammad Reza Vaezi. Palladium Nanoparticle-Decorated Porous Metal–Organic-Framework (Zr)@Guanidine: Novel Efficient Catalyst in Cross-Coupling (Suzuki, Heck, and Sonogashira) Reactions and Carbonylative Sonogashira under Mild Conditions. ACS Omega 2023, 8 (18) , 16395-16410. https://doi.org/10.1021/acsomega.3c01179
    2. Leila Mohammadi, Mojtaba Hosseinifard, Mohammad Reza Vaezi. Stabilization of Palladium-Nanoparticle-Decorated Postsynthesis-Modified Zr-UiO-66 MOF as a Reusable Heterogeneous Catalyst in C–C Coupling Reaction. ACS Omega 2023, 8 (9) , 8505-8518. https://doi.org/10.1021/acsomega.2c07661
    3. Chetna Yadav, Ajay Kumar Sahoo, Jarugu Narasimha Moorthy. Bottom-Up De Novo Synthesis of Porous Organic Polymers with Enone Functionalities as Supports for Pd and Cu Nanoparticles for Catalytic Tandem Synthesis. ACS Applied Nano Materials 2022, 5 (10) , 14296-14310. https://doi.org/10.1021/acsanm.2c02207
    4. Lijing Zhang, Jiaqi Han, Yuchao Wang, Wenbo Yang, Shengyang Tao. Pd/Mg(OH)2/MgO–ZrO2 Nanocomposite Systems for Highly Efficient Suzuki–Miyaura Coupling Reaction at Room Temperature: Implications for Low-Carbon Green Organic Synthesis. ACS Applied Nano Materials 2022, 5 (6) , 8059-8069. https://doi.org/10.1021/acsanm.2c01179
    5. Tiago F. Machado, Artur J.M. Valente, M. Elisa Silva Serra, Dina Murtinho. Diazo-coupled porous organic polymers as efficient catalysts for metal-free Henry and Knoevenagel reactions. Microporous and Mesoporous Materials 2023, 117 , 112561. https://doi.org/10.1016/j.micromeso.2023.112561
    6. Satyapriya Nath, Adithyan Puthukkudi, Jeebanjyoti Mohapatra, Suresh Bommakanti, Naisa Chandrasekhar, Bishnu P. Biswal. Carbon–Carbon Linked Organic Frameworks: An Explicit Summary and Analysis. Macromolecular Rapid Communications 2023, 1 , 2200950. https://doi.org/10.1002/marc.202200950
    7. Bingxin You, Yuyang Tian, Baolin Wang, Guangshan Zhu. Porous aromatic frameworks with high Pd nanoparticles loading as efficient catalysts for the Suzuki coupling reaction. Journal of Colloid and Interface Science 2022, 628 , 1023-1032. https://doi.org/10.1016/j.jcis.2022.08.026
    8. Maria Novoa-Cid, Arianna Melillo, Belén Ferrer, Mercedes Alvaro, Herme G. Baldovi. Photocatalytic Water Splitting Promoted by 2D and 3D Porphyrin Covalent Organic Polymers Synthesized by Suzuki-Miyaura Carbon-Carbon Coupling. Nanomaterials 2022, 12 (18) , 3197. https://doi.org/10.3390/nano12183197

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