Journal
CHEMELECTROCHEM
Volume 6, Issue 1, Pages 246-251Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/celc.201800578
Keywords
cascade reactions; electrochemistry; paper-based platform; Raman spectroscopy; stencil-printed electrodes
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Funding
- Army Research Office MURI grant [W911NF1410263]
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Benefits of utilizing cascade reactions for chemical synthesis include minimizing waste and decreasing experimentation times. However, these complex systems lack an efficient screening platform for evaluating their progression. A paper-based microfluidic platform was developed to monitor cascade systems without the need for off-line product verification. Two types of paper-based platforms were fabricated to facilitate this study: electrochemical and spectro-electrochemical. Electrochemical platforms were integrated with stencil-printed electrodes and used to perform electrochemical alcohol oxidation reactions with two derivatives of the organocatalyst TEMPO (TEMPO=2,2,6,6-tetramethylpiperidinyl-N-oxyl). The catalyst 4-amino-TEMPO (TEMPO-NH2) was used as a model catalyst that was studied not immobilized and immobilized (pyrene-amido-TEMPO) on electrochemical platforms. These platforms were designed to provide quasi-stationary flow allowing constant electrochemical data collection as catalytic reactions proceeded. TEMPO-NH2 and pyrene-amido-TEMPO were evaluated for the partial oxidation of glycerol and its intermediates. In comparison to TEMPO-NH2, the pyrene-amido-TEMPO catalyst produced higher current outputs. Spectro-electrochemical platforms were integrated with stencil-printed electrodes, and a surface enhanced Raman spectroscopy (SERS) detection zone. The spectro-electrochemical platforms allowed for catalytic conversions at the electrodes and subsequent delivery of catalytically transformed analytes to a SERS detection zone for product analysis. This platform was demonstrated for pyrene-amido-TEMPO and was shown to convert glycerol to mesoxalic acid. The experimental procedures for making components of the spectro-electrochemical device were described and include: preparation of the paper-based platform, construction of stencil-printed electrodes, and fabrication of SERS detection zones. These platforms provide an approach to analyzing multi-step cascade chemical reactions.
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