Synthesis of copper graphene materials functionalized by amino acids and their catalytic applications

ACS Applied Materials and Interfaces

Volumn 6, Issue 16, 2014, Pages 13502-13509

  Huang, Qiang ^a   Zhou, Limei ^a   Jiang, Xiaohui ^a   Zhou, Yafen ^a   Fan, Hongwei ^a   Lang, Wencheng ^a  

^a CHINA WEST NORMAL UNIVERSITY   (China)

Author keywords

amino acids; catalyst; copper; functionalized graphene; N arylation

Indexed keywords

AMINO ACIDS; AROMATIC COMPOUNDS; ATOMIC EMISSION SPECTROSCOPY; ATOMIC FORCE MICROSCOPY; CATALYST ACTIVITY; CATALYSTS; CHEMICAL MODIFICATION; COPPER; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAFTING (CHEMICAL); GRAPHENE; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; INDUCTIVELY COUPLED PLASMA; METAL NANOPARTICLES; SCANNING ELECTRON MICROSCOPY; X RAY PHOTOELECTRON SPECTROSCOPY;

CATALYTIC APPLICATIONS; CATALYTIC CHEMISTRY; COPPER NANOPARTICLES; FUNCTIONALIZED GRAPHENE; INDUCTIVELY COUPLED PLASMA ATOMIC EMISSION SPECTROMETRY; N-ARYLATION REACTIONS; N-ARYLATIONS; SYNERGISTIC EFFECT;

HYBRID MATERIALS;

EID: 84906815214     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am502586c     Document Type: Article

References (41)

1. 4@graphene composites as anode materials for high-performance lithium ion batteries Inorg. Chem. 2011, 50, 1628-1632
2. Shang, N.; Feng, C.; Zhang, H.; Gao, S.; Tang, R.; Wang, C.; Wang, Z. Suzuki-Miyaura reaction catalyzed by graphene oxide supported palladium nanoparticles Catal. Commun. 2013, 40, 111-115
3. Yan, J.; Wang, Z.; Wang, H.; Jiang, Q. Rapid and energy-efficient synthesis of a graphene-CuCo hybrid as a high performance catalyst J. Mater. Chem. 2012, 22, 10990-10993
4. Chen, Q.; Zhang, L.; Chen, G. Facile preparation of graphene-copper nanoparticle composite by in situ chemical reduction for electrochemical sensing of carbohydrates Anal. Chem. 2012, 84, 171-178
5. Zhang, Y.; Tian, J.; Li, H.; Wang, L.; Qin, X.; Asiri, A.; Al-Youbi, A.; Sun, X. Biomolecule-assisted, environmentally friendly, one-pot synthesis of CuS/reduced graphene oxide nanocomposites with enhanced photocatalytic performance Langmuir 2012, 28, 12893-12900
6. Chen, W.; Yan, L.; Bangal, P. Chemical reduction of graphene oxide to graphene by sulfur-containing compounds J. Phys. Chem. C 2010, 114, 19885-19890
7. Garg, B.; Ling, Y. Versatilities of graphene-based catalysts in organic transformations Green Mater. 2013, 1, 47-61
8. Bekyarova, E.; Itkis, M.; Ramesh, P.; Berger, C.; Sprinkle, M.; Heer, W.; Haddon, R. Chemical modification of epitaxial graphene: Spontaneous grafting of aryl groups J. Am. Chem. Soc. 2009, 131, 1336-1337
9. Hummers, W.; Offeman, R. Preparation of graphitic oxide J. Am. Chem. Soc. 1958, 80, 1339
10. Si, Y.; Samulski, E. Synthesis of water soluble graphene Nano Lett. 2008, 8, 1679-1682
11. He, H.; Gao, C. General approach to individually dispersed highly soluble and conductive graphene nanosheets functionalized by nitrene chemistry Chem. Mater. 2010, 22, 5054-5064
12. Georgakilas, V.; Bourlinos, A.; Zboril, R.; Steriotis, T.; Dallas, P.; Stubos, A.; Trapalis, C. Organic functionalisation of graphenes Chem. Commun. (Cambridge, U. K.) 2010, 46, 1766-1768
13. Kerscher, B.; Appel, A.; Thomann, R.; Mülhaupt, R. Treelike polymeric ionic liquids grafted onto graphene nanosheets Macromolecules 2013, 46, 4395-4402
14. 2 gas sensor J. Am. Chem. Soc. 2012, 134, 4905-4917
15. Mungse, H.; Verma, S.; Kumar, N.; Sain, B.; Khatri, O. Grafting of oxo-vanadium Schiff base on graphene nanosheets and its catalytic activity for the oxidation of alcohols J. Mater. Chem. 2012, 22, 5427-5433
16. Tan, R.; Li, C.; Luo, J.; Kong, Y.; Zheng, W.; Yin, D. An effective heterogeneous l -proline catalyst for the direct asymmetric aldol reaction using graphene oxide as support J. Catal. 2013, 298, 138-147
17. Shang, N.; Gao, S.; Feng, C.; Zhang, H.; Wang, C.; Wang, Z. Graphene oxide supported N-heterocyclic carbene-palladium as a novel catalyst for the Suzuki-Miyaura reaction RSC Adv. 2013, 3, 21863-21868
18. 2 nanoparticles for efficient aerobic cross-dehydrogenative coupling reaction in water Org. Lett. 2012, 14, 5992-5995
19. Fernández-Merino, M.; Villar-Rodil, S.; Paredes, J.; Solís-Fernández, P.; Guardia, L.; García, R.; Martínez-Alonso, A.; Tascón, J. Identifying efficient natural bioreductants for the preparation of graphene and graphene-metal nanoparticle hybrids with enhanced catalytic activity from graphite oxide Carbon 2013, 63, 30-44
20. Chen, W.; Zhang, Y.; Zhu, L.; Lan, J.; Xie, R.; You, J. A concept of supported amino acid ionic liquids and their application in metal scavenging and heterogeneous catalysis J. Am. Chem. Soc. 2007, 129, 13879-13886
21. Ma, D.; Cai, Q. Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles Acc. Chem. Res. 2008, 41, 1450-1460
22. Chen, Y.; Xie, X.; Ma, D. Facile access to polysubstituted indoles via a cascade Cu-catalyzed arylation-condensation process J. Org. Chem. 2007, 72, 9329-9334
23. Ma, D.; Cai, Q.; Zhang, H. Mild method for Ullmann coupling reaction of amines and aryl halides Org. Lett. 2003, 5, 2453-2455
24. Chen, D.; Li, L.; Guo, L. An environment-friendly preparation of reduced graphene oxide nanosheets via amino acid Nanotechnology 2011, 22, 325601-325608
25. Ouyang, Y.; Cai, X.; Shi, Q.; Liu, L.; Wan, D.; Tan, S.; Ouyang, Y. Poly- l -lysine-modified reduced graphene oxide stabilizes the copper nanoparticles with higher water-solubility and long-term additively antibacterial activity Colloids Surf., B 2013, 107, 107-114
26. Wu, T.; Wang, X.; Qiu, H.; Gao, J.; Wang, W.; Liu, Y. Graphene oxide reduced and modified by soft nanoparticles and its catalysis of the Knoevenagel condensation J. Mater. Chem. 2012, 22, 4772-4779
27. Movahed, S.; Esmatpoursalmani, R.; Bazgir, A. N-Heterocyclic carbene palladium complex supported on ionic liquid-modified graphene oxide as an efficient and recyclable catalyst for Suzuki reaction RSC Adv. 2014, 4, 14586-14593
28. Li, Z.; Liu, J.; Huang, Z.; Yang, Y.; Xia, C.; Li, F. One-pot synthesis of Pd nanoparticle catalysts supported on N-doped carbon and application in the domino carbonylation ACS Catal. 2013, 3, 839-845
29. Zhang, P.; Yuan, J.; Li, H.; Liu, X.; Xu, X.; Antonietti, M.; Wang, Y. Mesoporous nitrogen-doped carbon for copper-mediated Ullmann-type C-O/-N/-S cross-coupling reactions RSC Adv. 2013, 3, 1890-1895
30. Mondal, P.; Sinha, A.; Salam, N.; Roy, A.; Jana, N.; Islam, S. Enhanced catalytic performance by copper nanoparticle-graphene based composite RSC Adv. 2013, 3, 5615-5623
31. Qi, X.; Zhou, L.; Jiang, X.; Fan, H.; Fu, H.; Chen, H. Montmorillonite-supported copper(I) for catalyzing N-arylation of nitrogen heterocycles Chin. J. Catal. 2012, 33, 1877-1882
32. Qu, K.; Wu, L.; Ren, J.; Qu, X. Natural DNA-modified graphene/Pd nanoparticles as highly active catalyst for formic acid electro-oxidation and for the Suzuki reaction ACS Appl. Mater. Interfaces 2012, 4, 5001-5009
33. Fakhri, P.; Jaleh, B.; Nasrollahzadeh, M. Synthesis and characterization of copper nanoparticles supported on reduced graphene oxide as a highly active and recyclable catalyst for the synthesis of formamides and primary amines J. Mol. Catal. A: Chem. 2014, 383-384, 17-22
34. Liu, X.; Zhang, J.; Guo, X.; Wu, S.; Wang, S. Amino acid-assisted one-pot assembly of Au, Pt nanoparticles onto one-dimensional ZnO microrods Nanoscale 2010, 2, 1178-1184
35. Deng, D.; Jin, Y.; Cheng, Y.; Qi, T.; Xiao, F. Copper nanoparticles: Aqueous phase synthesis and conductive films fabrication at low sintering temperature ACS Appl. Mater. Interfaces 2013, 5, 3839-3846
36. Kumara, M.; Tripp, B.; Muralidharan, S. Self-assembly of metal nanoparticles and nanotubes on bioengineered flagella scaffolds Chem. Mater. 2007, 19, 2056-2064
37. 4 nanoparticles hybridized with graphene sheets ChemPlusChem 2014, 79, 716-724
38. Ke, H.; Chen, X.; Zou, G. N-Heterocyclic carbene/phosphite synergistically assisted Pd/C-catalyzed Suzuki coupling of aryl chlorides Appl. Organomet. Chem. 2014, 28, 54-60
39. Kim, A.; Lee, H.; Park, J.; Kang, H.; Yang, H.; Song, H.; Park, K. Highly efficient and reusable copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides Molecules 2009, 14, 5169-5178
40. Rout, L.; Jammi, S.; Punniyamurthy, T. Novel CuO nanoparticle catalyzed C-N cross coupling of amines with iodobenzene Org. Lett. 2007, 9, 3397-3399
41. 2O: A simple and efficient reusable catalyst for N-arylation of nitrogen-containing heterocycles with aryl halides Catal. Lett. 2008, 122, 344-348