Tandem diazonium salt electroreduction and click chemistry as a novel, efficient route for grafting macromolecules to gold surface

Mahouche, Samia; Mekni, Nejib Hussein; Abbassi, Leïla; Lang, Philippe; Perruchot, Christian; Jouini, Mohamed; Mammeri, Fayna; Turmine, Mireille; Romdhane, Hatem Ben; Chehimi, Mohamed M.

doi:10.1016/j.susc.2009.09.004

Cited by 54 publications

(38 citation statements)

References 37 publications

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“…The immobilized group affords specific chemical and physicochemical properties to the surface which are exploited in many application fields such as molecular electronics [5,6], energy conversion [7][8][9] and chemical [10][11][12] or biological [13,14] sensing. Depending on the aim of the work, it can also be used for further modification using chemical reaction such as click chemistry [15][16][17] and amine/carboxyl condensation [18,19] or to directly interrogate the functionalized surface.…”

Section: Introductionmentioning

confidence: 99%

New insight into 4-nitrobenzene diazonium reduction process: Evidence for a grafting step distinct from NO2 electrochemical reactivity

Richard

Evrard

Gros

2012

Journal of Electroanalytical Chemistry

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International audienceElectrochemical and spectroscopic investigations were performed in order to clarify the mechanism of 4-nitrobenzene diazonium reduction on glassy carbon in protic medium. The number and nature of the electron transfer processes were found to be strongly correlated to the electrode surface state. On polished electrode two different reduction peaks were observed. Selective electrolyses realized at the corresponding potential definitely proved that the grafting process actually occurs at a potential distinct from NO2 electroreduction, this latter inducing the presence of the quasi-reversible NO/NHOH redox couple at the electrode surface. These results were confirmed by XPS analyses. Furthermore, voltammetric experiments using Fe(CN)63- showed that the electrochemical properties of the modified electrode strongly depend on the potential applied for grafting, which modulates the nitro group oxidation state. All the results suggested that the electrode functionalization was more efficient when grafting and NO2 reduction were performed separately

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Section: Introductionmentioning

confidence: 99%

New insight into 4-nitrobenzene diazonium reduction process: Evidence for a grafting step distinct from NO2 electrochemical reactivity

Richard

Evrard

Gros

2012

Journal of Electroanalytical Chemistry

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“…Towards this end, aryl diazonium salts served to initiate a range of radical polymerizations, anionic polymerization of vinylic monomers as well as oxidative polymerization of conjugated monomers . In alternative strategies, diazonium salts were employed in Huisgen 1 , 3 ‐cycloaddition reactions to click alkynylated PEGs to azido‐functionalized gold, and azido‐functionalized poly(vinyl pyridine) to alkynylated carbon nanotubes . In other applications relevant to polymer chemistry, monomers bearing clickable groups were prepared by radical polymerization, while others were postfunctionalized by clickable groups such as azide or alkyne .…”

Section: Introductionmentioning

confidence: 99%

Diazonium interface chemistry and click polymerization: A novel route for carbon nanotube‐polytriazole nanocomposites

Bensghaïer

Salmi

Droumaguet

et al. 2015

Surface & Interface Analysis

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Multiwalled carbon nanotubes (MWCNTs) were modified with azidophenyl groups from the in situ generated 4‐azidobenzenediazonium salt to provide a nanoscale platform for the surface‐confined polyaddition of α‐ω‐bis (O‐propargyl) diethylene glycol and 1,3‐diazidopropane. The polyaddition in the presence of the azido‐functionalized MWCNTs (MWCNT‐N3) provided robust polytriazole‐grafted MWCNTs (MWCNT‐PTAz) that withstood ultrasonication. The end MWCNT‐PTAz nanocomposite and the reference materials pristine MWCNTs and MWCNT‐N3 were characterized by thermogravimetric analyses, XPS, IR, and Raman. Particularly, N1s XPS spectra aided the detection of azide and triazole rings at the surface of MWCNT‐N3 and PTAz, respectively. The high resolution C1s region from MWCNT‐PTAz clearly exhibits C‐N and C‐O components assigned to the triazole and diethylene glycol repeat units in the PTAz grafts. Examination of the ID/IG peak intensity ratio from Raman spectra indicate true covalent modification of the MWCNTs with diazonium salts. IR spectroscopy tracked the azide to triazole transformation. Thermal analysis indicates a substantial mass loading of the organic grafts levelling off at 37 wt/wt%. This works brings strong supporting evidence for the versatility of diazonium salts in constructing MWCNT‐polymer nanocomposites through polyaddition of clickable diazido and diethynyl dimers at the surface of clickable MWCNTs. Copyright © 2015 John Wiley & Sons, Ltd.

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“…This technique has proved especially useful when used with the click chemistry reaction proposed by Demko and Sharpless [10][11][12] as a means to functionalise electrode surfaces with a variety of groups, and shows great potential for further applications [1,13,14]. This click chemistry reaction uses Huisgen 1,3-dipolar cycloaddition between an alkyne and an azide in the presence of a Cu(I) catalyst to form a triazole link between a wide range of substituted azides and alkynes [1,[10][11][12][13][14][15]. This reaction has been used a great deal in the organic synthesis of various complex compounds [15][16][17][18][19], but has only recently been studied for its potential in surface modification.…”

Section: Introductionmentioning

confidence: 99%

“…This click chemistry reaction uses Huisgen 1,3-dipolar cycloaddition between an alkyne and an azide in the presence of a Cu(I) catalyst to form a triazole link between a wide range of substituted azides and alkynes [1,[10][11][12][13][14][15]. This reaction has been used a great deal in the organic synthesis of various complex compounds [15][16][17][18][19], but has only recently been studied for its potential in surface modification. The versatility, high yields, mild conditions and stability of the resulting 1,2,3-triazoles makes them particularly attractive for surface modification, and thus sensor development [1,[13][14][15][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

“…This reaction has been used a great deal in the organic synthesis of various complex compounds [15][16][17][18][19], but has only recently been studied for its potential in surface modification. The versatility, high yields, mild conditions and stability of the resulting 1,2,3-triazoles makes them particularly attractive for surface modification, and thus sensor development [1,[13][14][15][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

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Electrode modification using iron metallophthalocyanine through click chemistry and axial ligation with pyridine

Coates

Nyokong

2012

Journal of Electroanalytical Chemistry

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Tandem diazonium salt electroreduction and click chemistry as a novel, efficient route for grafting macromolecules to gold surface

Cited by 54 publications

References 37 publications

New insight into 4-nitrobenzene diazonium reduction process: Evidence for a grafting step distinct from NO2 electrochemical reactivity

New insight into 4-nitrobenzene diazonium reduction process: Evidence for a grafting step distinct from NO2 electrochemical reactivity

Diazonium interface chemistry and click polymerization: A novel route for carbon nanotube‐polytriazole nanocomposites

Electrode modification using iron metallophthalocyanine through click chemistry and axial ligation with pyridine

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