Electrochemistry and Reactivity of Surface-Confined Catechol Groups

Feb 12, 2009 - Ngoc Hoa Nguyen,† Charles Esnault,† Frédéric Gohier,† Daniel Bélanger,‡ and. Charles Cougnon*,†. Unité de Chimie Organiqu...
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Electrochemistry and reactivity of surface-confined catechol groups derived from diazonium reduction. Bias-assisted Michael addition at the solid|liquid interface. Ngoc Hoa Nguyen†, Frédéric Gohier†, Charles Esnault†, Daniel Bélanger‡. Charles Cougnon†,* Unité de Chimie Organique Moléculaire et Macromoléculaire (UCO2M, UMR CNRS 6011), Université du Maine, Avenue O. Messiaen, F-72085 Le Mans Cedex 9. Département de Chimie, Université du Québec à Montréal, Case Postale 8888, succursale Centre-Ville, Montréal, Québec, Canada H3C 3P8. [email protected], Fax: +33 (0)2 43 83 37 54

Supporting Information 10 8 6 4

I (µA)

2 0 -2-0.2

0.05

0.3

0.55

0.8

-4 -6 -8 -10 -12

E (V) vs. SCE

Figure S1 (A)

S1

80 60 40

I (µA)

20 0 -0.4 -20

-0.15

0.1

0.35

0.6

0.85

1.1

-40 -60 -80 -100

E (V) vs. SCE

Figure S1 (B) Figure S1 : CV recorded on a catechol-modified GC electrode in phosphate buffer solution at pH 7.08 for different sweep rates: (A) v = 0.005, 0.01, 0.02, 0.05 and 0.1 Vs-1, (B) v = 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.8 and 1 Vs-1.

S2

8

a

6 b

4

I (µA)

2 0 -0.3 -2

-0.05

0.2

0.45

0.7

-4 -6 -8 -10 -12

E (V) vs. SCE

Figure S2 : CVs in phosphate buffer solution pH 9.04 on a catechol-modified GC electrode before, curve a, and after, curve b, further derivatization by potential cycling (20 scans at 0.1 Vs-1) over the - 0.3 to + 0.5 V vs. SCE range in phosphate buffer solution containing 1 mM 2. Sweep rate: 0.1 Vs-1.

S3

Figure S3 : CVs in phosphate buffer solution pH 7.17 on a catechol-modified GC electrode after further derivatization by potential cycling (20 scans at 0.1 Vs-1) over the - 0.2 to + 0.6 V vs. SCE range in phosphate buffer solution containing 5 mM of 4nitrobenzyl alcohol. Sweep rate: 0.1 Vs-1.

S4

Figure S4 : CVs in phosphate buffer solution pH 7.17 on a catechol-modified GC electrode after further derivatization by potential cycling (20 scans at 0.1 Vs-1) over the - 0.2 to + 0.6 V vs. SCE range in phosphate buffer solution containing 5 mM of 4nitrobenzyl amine. Sweep rate: 0.1 Vs-1.

S5