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Fast and Versatile Functionalization of Glassy Carbon
Jasper Ainsworth1, Thomas C Cook1, T Daniel P Stack1
1Department of Chemistry, Stanford University, Stanford, California 94305, United States.
Langmuir : the ACS Journal of Surfaces and Colloids
|November 3, 2022
Summary
This study presents a fast, three-step method to covalently attach molecules to glassy carbon surfaces (GCSs) using click chemistry. This functionalization technique achieves high surface coverage and durability for various ethynylated compounds.
Area of Science:
- Electrochemistry
- Surface Chemistry
- Organic Synthesis
Background:
- Functionalization of glassy carbon surfaces (GCSs) is crucial for developing advanced electrochemical devices.
- Existing methods for surface modification can be time-consuming and require harsh conditions.
- Covalent attachment offers robust and stable surface modifications compared to physisorption.
Purpose of the Study:
- To develop a rapid and efficient procedure for the covalent functionalization of GCSs.
- To enable the attachment of ethynylated molecules to GCSs via a methylene linker.
- To evaluate the surface coverage, durability, and electrochemical properties of the functionalized surfaces.
Main Methods:
- A three-step sequence involving bromomethylation, azide displacement, and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC).
- Attachment of redox-active molecules like ethynyl ferrocene and a ruthenium complex ([RuII(Cl)(DMSO)(ethynyl-TPA)]1+).
- Characterization using cyclic voltammetry (CV) for surface coverage and X-ray photoelectron spectroscopy (XPS) for elemental composition.
Main Results:
- High surface coverages (1 × 1014 molecules/cm2) achieved in under 1 hour.
- Functionalized surfaces exhibit good durability in acidic and basic media.
- Attached ruthenium complex demonstrated catalytic activity for alcohol oxidation, though with modified electrochemical performance compared to direct attachment.
Conclusions:
- The developed three-step procedure provides a rapid, mild, and versatile method for GCS functionalization.
- This approach allows for the covalent attachment of diverse ethynylated molecules, expanding possibilities for surface engineering.
- The method offers advantages in terms of reaction time, conditions, and reagent accessibility for surface modification applications.
