Synthesis of Copper Graphene Materials Functionalized by Amino Acids and Their Catalytic Applications

被引:59
作者
Huang, Qiang [1 ]
Zhou, Limei [1 ]
Jiang, Xiaohui [1 ]
Zhou, Yafen [1 ]
Fan, Hongwei [1 ]
Lang, Wencheng [1 ]
机构
[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Sichuan, Peoples R China
关键词
functionalized graphene; copper; catalyst; amino acids; N-arylation; NITROGEN-CONTAINING HETEROCYCLES; SUZUKI-MIYAURA REACTION; ONE-POT SYNTHESIS; ARYL HALIDES; N-ARYLATION; RECYCLABLE CATALYST; CHEMICAL-REDUCTION; CARBENE-PALLADIUM; COUPLING REACTION; IONIC LIQUIDS;
D O I
10.1021/am502586c
中图分类号
TB3 [工程材料学];
学科分类号
0805 ; 080502 ;
摘要
Graphene oxide and its derivative have attracted extensive interests in many fields, including catalytic chemistry, organic synthesis, and electrochemistry, recently. We explored whether the use of graphene after chemical modification with amino acids to immobilize copper nanoparticles could achieve a more excellent catalytic activity for Narylation reactions. A facile and novel method to prepare copper supported on amino-acid-grafted graphene hybrid materials (A-G-Cu) was first reported. The as-prepared hybrid materials were characterized by a variety of techniques, including Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, X-ray diffraction, scanning electron microscopy, atomic force microscopy, transmission electron microscopy, and inductively coupled plasma atomic emission spectrometry. The results showed that the morphology, distribution, and loading of copper nanopartides could be well-adjusted by controlling the type of amino acids grafted on graphene. Moreover, most A-G-Cu hybrid materials could catalyze N-arylation of imidazole with iodobenzene with yields more than 90%, while the copper supported on graphene (G-Cu) displayed a yield of just 65.8%. The high activity of A-G-Cu can be ascribed to the good synergistic effects of copper nanoparticles (Cu NPs) and amino-acid-grafted graphene.
引用
收藏
页码:13502 / 13509
页数:8
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共 41 条
  • [21] One-Pot Synthesis of Pd Nanoparticle Catalysts Supported on N-Doped Carbon and Application in the Domino Carbonylation
    Li, Zelong
    Liu, Jianhua
    Huang, Zhiwei
    Yang, Ying
    Xia, Chungu
    Li, Fuwei
    [J]. ACS CATALYSIS, 2013, 3 (05): : 839 - 845
  • [22] Enhanced Aerobic Epoxidation of Styrene with Copper(II), Cobalt(II), Iron(III), or Oxovanadium(IV) Salen Complexes Immobilized onto Carbon-Coated Fe3O4 Nanoparticles Hybridized with Graphene Sheets
    Li, Zhifang
    Wu, Shujie
    Zheng, Dafang
    Ding, Hong
    Wang, Xiufang
    Yang, Xiaoyuan
    Huo, Qisheng
    Guan, Jingqi
    Kan, Qiubin
    [J]. CHEMPLUSCHEM, 2014, 79 (05): : 716 - 724
  • [23] Amino acid-assisted one-pot assembly of Au, Pt nanoparticles onto one-dimensional ZnO microrods
    Liu, Xianghong
    Zhang, Jun
    Guo, Xianzhi
    Wu, Shihua
    Wang, Shurong
    [J]. NANOSCALE, 2010, 2 (07) : 1178 - 1184
  • [24] Copper/Amino Acid Catalyzed Cross-Couplings of Aryl and Vinyl Halides with Nucleophiles
    Ma, Dawei
    Cai, Qian
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1450 - 1460
  • [25] Mild method for Ullmann coupling reaction of amines and aryl halides
    Ma, DW
    Cai, Q
    Zhang, H
    [J]. ORGANIC LETTERS, 2003, 5 (14) : 2453 - 2455
  • [26] Graphene-Supported RuO2 Nanoparticles for Efficient Aerobic Cross-Dehydrogenative Coupling Reaction in Water
    Meng, Qing-Yuan
    Liu, Qiang
    Zhong, Jian-Ji
    Zhang, Hui-Hui
    Li, Zhi-Jun
    Chen, Bin
    Tung, Chen-Ho
    Wu, Li-Zhu
    [J]. ORGANIC LETTERS, 2012, 14 (23) : 5992 - 5995
  • [27] Enhanced catalytic performance by copper nanoparticle-graphene based composite
    Mondal, Paramita
    Sinha, Arjyabaran
    Salam, Noor
    Roy, Anupam Singha
    Jana, Nikhil R.
    Islam, S. M.
    [J]. RSC ADVANCES, 2013, 3 (16) : 5615 - 5623
  • [28] N-Heterocyclic carbene palladium complex supported on ionic liquid-modified graphene oxide as an efficient and recyclable catalyst for Suzuki reaction
    Movahed, Siyavash Kazemi
    Esmatpoursalmani, Rahele
    Bazgir, Ayoob
    [J]. RSC ADVANCES, 2014, 4 (28) : 14586 - 14591
  • [29] Grafting of oxo-vanadium Schiff base on graphene nanosheets and its catalytic activity for the oxidation of alcohols
    Mungse, Harshal P.
    Verma, Sanny
    Kumar, Neeraj
    Sain, Bir
    Khatri, Om P.
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (12) : 5427 - 5433
  • [30] Poly-L-lysine-modified reduced graphene oxide stabilizes the copper nanoparticles with higher water-solubility and long-term additively antibacterial activity
    Ouyang, Yu
    Cai, Xiang
    Shi, QingShan
    Liu, Lili
    Wan, Dongliang
    Tan, Shaozao
    Ouyang, Yousheng
    [J]. COLLOIDS AND SURFACES B-BIOINTERFACES, 2013, 107 : 107 - 114