Spontaneous derivatization of a copper electrode with in situ generated diazonium cations in aprotic and aqueous media

被引:69
作者
Chamoulaud, Gwenael [1 ]
Belanger, Daniel [1 ]
机构
[1] Univ Quebec, Dept Chim, Montreal, PQ H3C 3P8, Canada
关键词
D O I
10.1021/jp0704012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Spontaneous derivatization of copper electrode surfaces with 4-nitrophenyl groups from the corresponding diazonium cations, in situ generated, in aprotic (0.1 M NEt4BF4 in ACN) and aqueous acidic (0.1 M CH3COOH) medium is described. The 4-nitrophenyl diazonium cations were synthesized in the electrochemical cell by reaction of 4-nitroaniline with tert-butyl nitrite in aprotic media and with NaNO2 in aqueous media. Derivatized copper electrode surfaces were characterized by cyclic voltammetry, Fourier transform infrared reflection absorption spectroscopy, and X-ray photoelectron spectroscopy. The main finding of this study was the spontaneous formation of multilayered coating in aprotic media and the spontaneous formation of close to a monolayer coating in aqueous acid media. The effect of the experimental conditions leading to the formation of the grafted layer in aqueous acidic media was also investigated. The limitations of the approach involving in situ generated diazonium cations relative to that making use of a diazonium salt are also presented.
引用
收藏
页码:7501 / 7507
页数:7
相关论文
共 45 条
[31]   SELF-ASSEMBLED MONOLAYERS OF N-ALKANETHIOLATES ON COPPER ARE BARRIER FILMS THAT PROTECT THE METAL AGAINST OXIDATION BY AIR [J].
LAIBINIS, PE ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :9022-9028
[32]   REACTIONS OF ORGANIC MONOLAYERS ON CARBON SURFACES OBSERVED WITH UNENHANCED RAMAN-SPECTROSCOPY [J].
LIU, YC ;
MCCREERY, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) :11254-11259
[33]   Direct modification of a gold electrode with aminophenyl groups by electrochemical reduction of in situ generated aminophenyl monodiazonium cations [J].
Lyskawa, Joel ;
Belanger, Daniel .
CHEMISTRY OF MATERIALS, 2006, 18 (20) :4755-4763
[34]   Surface modification of indium tin oxide via electrochemical reduction of aryldiazonium cations [J].
Maldonado, S ;
Smith, TJ ;
Williams, RD ;
Morin, S ;
Barton, E ;
Stevenson, KJ .
LANGMUIR, 2006, 22 (06) :2884-2891
[35]   Functionalization of glassy carbon electrodes with metal-based species [J].
Marwan, J ;
Addou, T ;
Bélanger, D .
CHEMISTRY OF MATERIALS, 2005, 17 (09) :2395-2403
[36]   A novel example of X-ray-radiation-induced chemical reduction of an aromatic nitro-group-containing thin film on SiO2 to an aromatic amine film [J].
Mendes, P ;
Belloni, M ;
Ashworth, M ;
Hardy, C ;
Nikitin, K ;
Fitzmaurice, D ;
Critchley, K ;
Evans, S ;
Preece, J .
CHEMPHYSCHEM, 2003, 4 (08) :884-889
[37]   Electrochemical modification of benzo-15-crown-5 ether on a glassy carbon electrode for alkali metal cation recognition [J].
Morita, K ;
Yamaguchi, A ;
Teramae, N .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2004, 563 (02) :249-255
[38]   Electrochemical modification of a carbon electrode using aromatic diazonium salts. 2. Electrochemistry of 4-nitrophenyl modified glassy carbon electrodes in aqueous media [J].
Ortiz, B ;
Saby, C ;
Champagne, GY ;
Belanger, D .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1998, 455 (1-2) :75-81
[39]   Homogeneous chemical derivatisation of carbon particles: a novel method for funtionalising carbon surfaces [J].
Pandurangappa, M ;
Lawrence, NS ;
Compton, RG .
ANALYST, 2002, 127 (12) :1568-1571
[40]   Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts [J].
Pinson, J ;
Podvorica, F .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (05) :429-439