Skip to main content
SpringerLink
Log in

Gold nanodots self-assembled polyelectrolyte film as reusable catalyst for reduction of nitroaromatics

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Separation of homogeneous catalyst from the reaction mixture is a crucial and difficult process in any catalytic process. To address this issue, a new class of multifunctional catalyst in the form of film was developed using a facile approach to enjoy the advantages of homogeneous catalyst with the versatility of heterogeneous catalyst. To achieve the same, methionine-capped gold nanodots (AuNDs) were self-assembled on a cationic polyelectrolyte modified glass plate for the catalytic reduction of nitro functional groups in the presence of olefinic double bond at mild conditions. Separation of this reusable catalytic film from the reaction mixture is very simple and advantageous when compared to the currently available and conventional catalytic systems. Kinetics of nitro reduction was monitored using absorption spectroscopy and the product formation was confirmed by \(^{1}\hbox {H}\) and \(^{13}\hbox {C}\,\hbox {NMR}\) analyses. Prepared AuNDs catalyst was characterized using UV-Vis spectroscopy, X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), high-resolution transmission electron microscopy (HRTEM), cyclic voltammetry and atomic force microscopy (AFM) techniques.

Graphical Abstract

 SYNOPSIS Colloidal gold nanoparticles are efficient catalysts for organic reactions. But the removal of homogeneous gold colloids from the reaction mixture is very difficult. To address this issue, gold nanodots were synthesized and self-assembled over polyelectrolyte film to form catalytic plates. Removal of these reusable catalytic plates from the reaction mixture is facile.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Thomas J M and Thomas W J 1997 (Eds.) In Principles and Practice of Heterogeneous Catalysis (VCH: Weinheim)

  2. An K and Somorjai G A 2015 Nanocatalysis I: synthesis of metal and bimetallic nanoparticles and porous oxides and their catalytic reaction studies Catal. Lett. 145 233

    Article  CAS  Google Scholar 

  3. Daniel M-C and Astruc D 2004 Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology Chem. Rev. 104 293

    Article  CAS  Google Scholar 

  4. Tamiolakis I, Fountoulaki S, Vordos N, Lykakisb I N and Armatas G S 2013 Mesoporous Au–\(\text{TiO}_{2}\) Nanoparticle assemblies as efficient catalysts for the chemoselective reduction of nitrocompounds J. Mater. Chem. A 1 14311

  5. Rathore P S, Patidar R, Shripathic T and Thakore S 2015 Magnetically separable core–shell iron oxide@nickel nanoparticles as high-performance recyclable catalysts for chemoselective reduction of nitroaromatics Catal. Sci. Technol. 5 286

    Article  CAS  Google Scholar 

  6. Guerrero E, Munoz-Marquez M A, Garcıa M A, Crespo P, Fernandez-Pinel E, Hernando A and Fernandez A 2008 Surface plasmon resonance and magnetism of thiol-capped gold nanoparticles Nanotechnology 19 175701

  7. Templeton A C, Chen S, Gross S M and Murray R W 1999 Water-soluble isolable gold clusters protected by tiopronin and coenzyme A monolayers Langmuir 15 66

    Article  CAS  Google Scholar 

  8. Bourg M-C, Badia A and Lennox R B 2000 Gold-sulfur bonding in 2D and 3D self-assembled monolayers: XPS characterization J. Phys. Chem. B 104 6562

    Article  CAS  Google Scholar 

  9. Gaur S, Miller J T, Stellwagen D, Sanampudi A, Kumar C S S R and Spivey J J 2012 Synthesis, characterization, and testing of supported Au catalysts prepared from atomically-tailored \(\text{ Au }_{38}\)(SC12H25)24 clusters Phys. Chem. Chem. Phys. 14 1627

    Article  CAS  Google Scholar 

  10. Angelova P, Solel, E, Parvari G, Turchanin A, Botoshansky M, Gölzhauser A and Keinan E 2013 Chemisorbed monolayers of corannulene penta-thioethers on gold Langmuir 29 2217

    Article  CAS  Google Scholar 

  11. Tseng R J, Baker C O, Shedd B, Huang J, Kaner R B, Ouyang J and Yang Y 2007 Charge transfer effect in the polyaniline-gold nanoparticle memory system Appl. Phys. Lett. 90 053101

    Article  Google Scholar 

  12. Qiu L, Liu F, Zhao L, Yang W and Yao J 2006 Evidence of a unique electron donor-acceptor property for platinum nanoparticles as studied by XPS Langmuir 22 4480

    Article  CAS  Google Scholar 

  13. Viswanathan P and Ramaraj R 2017 Preparation of polyelectrolyte-stabilized silver nanoparticles for catalytic applications Polym. Int. 66 342

    Article  CAS  Google Scholar 

  14. Tian N, Zhou Z-Y, Sun S-G, Ding Y and Wang Z L 2007 Synthesis of tetrahexahedral platinum nanocrystals with high-index facets and high electro-oxidation activity Science 316 732

    Article  CAS  Google Scholar 

  15. Viswanathan P and Ramaraj R 2016 Polyelectrolyte assisted synthesis and enhanced catalysis of silver nanoparticles: electrocatalytic reduction of hydrogen peroxide and catalytic reduction of 4-nitroaniline J. Mol. Catal. A Chem. 424 128

    Article  CAS  Google Scholar 

  16. Henglein A and Lilie J 1981 Storage of electrons in aqueous solution: the rates of chemical charging and discharging the colloidal silver microelectrode J. Am. Chem. Soc. 103 1059

    Article  CAS  Google Scholar 

  17. Chiu C-Y, Chung P-J, Lao K-U, Liao C-W and Huang M H 2012 Facet-dependent catalytic activity of gold nanocubes, octahedra, and rhombic dodecahedra toward 4-nitroaniline reduction J. Phys. Chem. C 116 23757

    Article  CAS  Google Scholar 

  18. Zhu C, Han L, Hu P and Dong S 2012 In situ loading of well-dispersed gold nanoparticles on two-dimensional graphene oxide/\(\text{ SiO }_{2}\) composite nanosheets and their catalytic properties Nanoscale 4 1641

    Article  CAS  Google Scholar 

  19. Fenger R, Fertitta E, Kirmse H, Thunemann A F and Rademann K 2012 Size dependent catalysis with CTAB-stabilized gold nanoparticles Phys. Chem. Chem. Phys. 14 9343

    Article  CAS  Google Scholar 

  20. Seo E, Kim J, Hong Y, Kim Y S, Lee D and Kim B S 2013 Double hydrophilic block copolymer templated Au nanoparticles with enhanced catalytic activity toward nitroarene reduction J. Phys. Chem. C 117 11686

    Article  CAS  Google Scholar 

  21. Li M and Chen G 2013 Revisiting catalytic model reaction P-nitrophenol/\(\text{ NaBH }_{4}\) using metallic nanoparticles coated on polymeric spheres Nanoscale 5 11919

    Article  CAS  Google Scholar 

  22. Biondi I, Laurenczy G and Dyson P J 2011 Synthesis of gold nanoparticle catalysts based on a new water-soluble ionic polymer Inorg. Chem. 50 8038

    Article  CAS  Google Scholar 

  23. Esumi K, Miyamoto K and Yoshimura T 2003 Morphological change of gold–dendrimer nanocomposites by laser irradiation J. Colloid Interface Sci. 268 501

    Article  CAS  Google Scholar 

  24. Hayakawa K, Yoshimura T and Esumi K 2003 Preparation of gold-dendrimer nanocomposites by laser irradiation and their catalytic reduction of 4-nitrophenol Langmuir 19 5517

    Article  CAS  Google Scholar 

  25. Wang X, Long Y, Wang Q, Zhang H, Huang X, Zhu R, Teng P, Liang L and Zheng H Z 2013 Reduced state carbon dots as both reductant and stabilizer for the synthesis of gold nanoparticles Carbon 64 499

    Article  CAS  Google Scholar 

  26. Fan C M, Zhang L F, Wang S S, Wang D H, Lu L Q and Xu A W 2012 Novel \(\text{ CeO }_{2}\) yolk–shell structures loaded with tiny Au nanoparticles for superior catalytic reduction of \(p\)-nitrophenol Nanoscale 4 6835

  27. Xiao C, Chen S, Zhang L, Zhou S and Wu W 2012 One-pot synthesis of responsive catalytic Au@PVP hybrid nanogels Chem. Commun. 48 11751

    Article  CAS  Google Scholar 

  28. Huang T, Meng F and Qi L 2009 Facile synthesis and one-dimensional assembly of cyclodextrin-capped gold nanoparticles and their applications in catalysis and surface-enhanced raman scattering J. Phys. Chem. C 113 13636

    Article  CAS  Google Scholar 

  29. Han J, Li L and Guo R 2010 Novel approach to controllable synthesis of gold nanoparticles supported on polyaniline nanofibers Macromolecules 43 10636

    Article  CAS  Google Scholar 

  30. Kelly S M and Lipshutz B H 2014 Chemoselective reductions of nitroaromatics in water at room temperature Org. Lett. 16 98

    Article  CAS  Google Scholar 

  31. Dotzauer D M, Bhattacharjee S, Wen Y and Bruening M 2009 Nanoparticle-containing membranes for the catalytic reduction of nitroaromatic compounds Langmuir 25 1865

    Article  CAS  Google Scholar 

  32. Blaser H-U, Siegrist U and Steiner H 2001 In Aromatic Nitro Compounds: Fine Chemicals through Heterogeneous Catalysis (Wiley-VCH: Weinheim) p. 389

Download references

Acknowledgements

RR acknowledges the financial support received from the CSIR-Emeritus Scientist Scheme, New Delhi. PV is the recipient of Senior Research Fellowship under UGC-BSR scheme.

Author information

Authors and Affiliations

  1. School of Chemistry, Centre for Photoelectrochemistry, Madurai Kamaraj University, Madurai, Tamilnadu, 625 021, India

    Perumal Viswanathan & Ramasamy Ramaraj

Authors
  1. Perumal Viswanathan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ramasamy Ramaraj
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ramasamy Ramaraj.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (pdf 1153 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Viswanathan, P., Ramaraj, R. Gold nanodots self-assembled polyelectrolyte film as reusable catalyst for reduction of nitroaromatics. J Chem Sci 130, 4 (2018). https://doi.org/10.1007/s12039-017-1405-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-017-1405-0

Keywords

Search

Navigation