Abstract
Electrochemical approaches provide useful tools for studying interfacial reactions. Interfacial reactions are often controlled by various factors in a different manner from that of bulk reactions. Understanding these differences is important for many applications. Particularly, the acid-base properties play a significant role in determining the characteristics of the surface and the reactions that take place on the surface. We investigated how the protonation and deprotonation of the surface-confined acid affected the interfacial Diels-Alder reaction occurring on gold electrode using cyclic voltammetry. The rate of Diels-Alder reaction showed a negative correlation to the extent of surface ionization, showing a response similar to a titration curve. The half maximum rate was observed at pH 7, which agreed with the pKa of surface-confined carboxylic acid. Subsequent investigation suggested that this dependence is likely due to the direct interaction of H-bonding between quinone and the surface-confined acid rather than the field effect.
Original language | English |
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Pages (from-to) | 41-46 |
Number of pages | 6 |
Journal | Journal of Electroanalytical Chemistry |
Volume | 720-721 |
DOIs | |
State | Published - 15 Apr 2014 |
Keywords
- Cyclic voltammetry
- Electrochemistry
- Interfacial organic reactions
- Self-assembled monolayers
- Surface-confined acid