N-halamine coatings formed via the electroreduction of in situ generated diazonium cations: toward antimicrobial surfaces

被引:3
作者
Gao, Shan [1 ]
Cachet, Hubert [1 ]
Debiemme-Chouvy, Catherine [1 ]
机构
[1] Univ Paris 06, Sorbonne Univ, CNRS, Lab Interfaces & Syst Electrochim,UMR 8235, 4 Pl Jussieu, F-75005 Paris, France
关键词
diazonium; EQCM; N-halamine; p-phenylenediamine; antimicrobial coating; aminophenyl film; ELECTROCHEMICAL REDUCTION; ORGANIC LAYERS; TIN DIOXIDE; ELECTRODE; SALTS; GOLD; ION;
D O I
10.1002/sia.5926
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
Nowadays, antimicrobial N-halamine polymers and coatings are extensively studied thanks to their qualities such as effectiveness toward a broad spectrum of microorganisms and regenerability. An N-halamine organic polymer contains nitrogen-halogen covalent bonds. Its antimicrobial properties are due to the oxidizing power of the halide atoms, which are at the oxidation state+I in chloramine (>N-Cl) or bromamine (>N-Br) groups. The aim of the present work was to generate a new N-halamine coating in a two-step route. First, we have synthesized by electroreduction of in situ generated aminophenyl diazonium cations polyaminophenyl films because these films contain numerous amino functions. Electrochemical quartz crystal microbalance (EQCM) allowed us to determine the mass of the film formed by cyclic voltammetry and to estimate its thickness; the highest one is about 1 mu m. Then, the second step of the process was the formation of haloamine functions into the polyaminophenyl film by substitution of H atoms of the amine functions by Br or Cl atoms. The films were observed by SEM, and their composition was determined by Energy-dispersive X-ray spectroscopy (EDS). Finally, the EQCM experiments allowed us to estimate that the N-halamine films that we have prepared contain one Cl atom or one Br atom for 4 or 4.5 phenyl groups, respectively. Copyright (c) 2016 John Wiley & Sons, Ltd.
引用
收藏
页码:630 / 635
页数:6
相关论文
共 21 条
[1]   Electrochemical derivatization of carbon surface by reduction of in situ generated diazonium cations [J].
Baranton, S ;
Bélanger, D .
JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (51) :24401-24410
[2]   Electrografting: a powerful method for surface modification [J].
Belanger, Daniel ;
Pinson, Jean .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3995-4048
[3]   X-ray photoelectron spectroscopy evidence for the covalent bond between an iron surface and aryl groups attached by the electrochemical reduction of diazonium salts [J].
Boukerma, K ;
Chehimi, MM ;
Pinson, J ;
Blomfield, C .
LANGMUIR, 2003, 19 (15) :6333-6335
[4]   Electrochemical treatments using tin oxide anode to prevent biofouling [J].
Debiemme-Chouvy, C. ;
Hua, Y. ;
Hui, F. ;
Duval, J. -L. ;
Cachet, H. .
ELECTROCHIMICA ACTA, 2011, 56 (28) :10364-10370
[5]   An original route to immobilize an organic biocide onto a transparent tin dioxide electrode [J].
Debiemme-Chouvy, Catherine ;
Haskouri, Sanae ;
Folcher, Guy ;
Cachet, Hubert .
LANGMUIR, 2007, 23 (07) :3873-3879
[6]   Study by XPS of the chlorination of proteins aggregated onto tin dioxide during electrochemical production of hypochlorous acid [J].
Debiemme-Chouvy, Catherine ;
Haskouri, Sanae ;
Cachet, Hubert .
APPLIED SURFACE SCIENCE, 2007, 253 (12) :5506-5510
[7]   Surface modification of conducting substrates. Existence of azo bonds in the structure of organic layers obtained from diazonium salts [J].
Doppelt, Pascal ;
Hallais, Geraldine ;
Pinson, Jean ;
Podvorica, Fetah ;
Verneyre, Sylvie .
CHEMISTRY OF MATERIALS, 2007, 19 (18) :4570-4575
[8]  
Downard AJ, 2000, ELECTROANAL, V12, P1085, DOI 10.1002/1521-4109(200010)12:14<1085::AID-ELAN1085>3.0.CO
[9]  
2-A
[10]   Electrochemical grafting of organic coating onto gold surfaces:: Influence of the electrochemical conditions on the grafting of nitrobenzene diazonium salt [J].
Haccoun, Julien ;
Vautrin-Ul, Christine ;
Chausse, Annie ;
Adenier, Alain .
PROGRESS IN ORGANIC COATINGS, 2008, 63 (01) :18-24