Self-Limited Grafting of Sub-Monolayers via Diels-Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight

被引:10
作者
Al Dine, Walaa Nasser [1 ,2 ]
Mehdi, Ahmad [1 ]
BouMalham, Ibrahim [3 ]
Herro, Ziad [2 ]
Vioux, Andre [1 ]
Brun, Nicolas [1 ]
Fontaine, Olivier [1 ,4 ]
机构
[1] Univ Montpellier, ENSCM, CNRS, ICGM, Montpellier, France
[2] Univ Libanaise, Fac Sci 2, Plateforme Rech Nanosci & Nanotechnol, BP 90656, Fanar, Lebanon
[3] Univ Libanaise, Fac Sci 4, Lab Energet & Reactivite Echelle Nanometr EREN, Haouch El Omara 1801, Zahle, Lebanon
[4] FR CNRS, Reseau Stockage Electrochim Energie RS2E, F-80039 Amiens, France
关键词
FUNCTIONALIZATION; SURFACE; NANOTUBES; IMMOBILIZATION; REDUCTION; IMPACT; SALT;
D O I
10.1021/acsomega.9b02391
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The grafting of molecular monolayers is critical for the functionalization of surfaces. In molecular electrochemistry, the surface modification of electrodes and the way molecules are attached to the electrode surface are highly critical to electron transfers and electrochemical reactions. In this paper, sub-monolayers were covalently grafted onto glassy carbon (GC) electrodes via Diels-Alder cycloaddition with two soluble dienophiles, that is, propargyl bromide and ethynyl ferrocene. Such an approach is clean (no by-product, no catalyst/additive) and occurs under mild conditions by heating at 50 degrees C in toluene for few hours. The as-modified electrodes were thoroughly characterized by FTIR, XPS, and cyclic voltammetry using both millimetric GC electrodes and ultra-microelectrodes. Cyclic voltammetry gave access to surface coverage and clearly evidenced the covalent grafting of sub-monolayers. The grafting of functional sub-monolayers via Diels- Alder cycloaddition could be easily extended to various functionalities and carbons to prepare electrochemical sensors or electrocatalytic surfaces.
引用
收藏
页码:20540 / 20546
页数:7
相关论文
共 32 条
[1]  
Alkire R. C., 2015, ELECTROCHEMISTRY CAR, P450
[2]  
Alkire R. C., 2008, ELECTROCHEMICAL SURF, V10, P360
[3]   CHARGE-TRANSFER AT PARTIALLY BLOCKED SURFACES - A MODEL FOR THE CASE OF MICROSCOPIC ACTIVE AND INACTIVE SITES [J].
AMATORE, C ;
SAVEANT, JM ;
TESSIER, D .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1983, 147 (1-2) :39-51
[4]   Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: A bucky paper electrode [J].
Bahr, JL ;
Yang, JP ;
Kosynkin, DV ;
Bronikowski, MJ ;
Smalley, RE ;
Tour, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6536-6542
[5]   Highly functionalized carbon nanotubes using in situ generated diazonium compounds [J].
Bahr, JL ;
Tour, JM .
CHEMISTRY OF MATERIALS, 2001, 13 (11) :3823-+
[6]   CHEMICAL MODIFICATION OF ELECTRODES [J].
BARD, AJ .
JOURNAL OF CHEMICAL EDUCATION, 1983, 60 (04) :302-304
[7]   Electrografting: a powerful method for surface modification [J].
Belanger, Daniel ;
Pinson, Jean .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3995-4048
[8]   Functionalised single wall carbon nanotubes/polypyrrole composites for the preparation of amperometric glucose biosensors [J].
Callegari, A ;
Cosnier, S ;
Marcaccio, M ;
Paolucci, D ;
Paolucci, F ;
Georgakilas, V ;
Tagmatarchis, N ;
Vázquez, E ;
Prato, M .
JOURNAL OF MATERIALS CHEMISTRY, 2004, 14 (05) :807-810
[9]   Microwave-assisted sidewall functionalization of single-wall carbon nanotubes by Diels-Alder cycloaddition [J].
Delgado, JL ;
de la Cruz, P ;
Langa, F ;
Urbina, A ;
Casado, J ;
Navarrete, JTL .
CHEMICAL COMMUNICATIONS, 2004, (15) :1734-1735
[10]   Functionalization of single-walled carbon nanotubes with 1,4-benzenediamine using a diazonium reaction [J].
Ellison, Mark D. ;
Gasda, Patrick J. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (03) :738-740