A Multifunctional Microfluidic Platform for High-Throughput Experimentation of Electroorganic Chemistry

Article abstract of DOI:10.1002/anie.202009819

Electroorganic synthesis is a promising tool to design sustainable transformations and discover new reactivities. However, the added setup complexity caused by electrodes in the system impedes efficient screening of reaction conditions. Herein, we present a microfluidic platform that enables automated high-throughput experimentation (HTE) for electroorganic synthesis at a 15-microliter scale. Two HTE modules are demonstrated: 1) the rapid electrochemical reaction condition screening for a radical–radical cross-coupling reaction on micro-fabricated interdigitated electrodes, and 2) measurements of kinetics for mediated anodic oxidations using the microliter-scale cyclic voltammetry. The presented modular approach could be deployed for a range of other electroorganic chemistry applications beyond the demonstrated functionalities.

Full text of DOI:10.1002/anie.202009819

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Accepted Article
Title: A multifunctional microfluidic platform for high-throughput
experimentation of electroorganic chemistry
Authors: Yiming Mo, Girish Rughoobur, Anirudh Manoj K Nambiar,
Kara Zhang, and Klavs F. Jensen
This manuscript has been accepted after peer review and appears as an
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.202009819
Link to VoR: https://doi.org/10.1002/anie.202009819

10.1002/anie.202009819
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COMMUNICATION
Multifunctional Microfluidic Platform for High-Throughput
Experimentation of Electroorganic Chemistry
Yiming Mo[a], Girish Rughoobur[b], Anirudh M. K. Nambiar[a], Kara Zhang[a], and Klavs F. Jensen*[a]
[a]
[b]
Dr. Y. Mo, A. M. K. Nambiar, K. Zhang, Prof. K. F. Jensen
Department of Chemical Engineering
Massachusetts Institute of Technology
77 Massachusetts Avenue, Cambridge, MA 02139 (USA)
E-mail: kfjensen@mit.edu
Dr. G. Rughoobur
Electrical Engineering and Computer Science
Massachusetts Institute of Technology
77 Massachsuetts Avenue, Cambridge, MA 02139 (USA)
Supporting information for this article is given via a link at the end of the document.
Abstract: Electroorganic synthesis is a promising tool to design
sustainable transformations and discover new reactivities. However,
the added setup complexity caused by electrodes in the system
impedes efficient screening of reaction conditions. Herein, we present
the development process. On the other hand, implementing
electrochemistry in microfluidic devices can also accelerate
reaction screening and optimization because of the reduced
electrolysis time brought by the increased electrode surface area
to volume ratio and the improved cell conductivity.[16–19]
a
microfluidic platform that enables automated high-throughput
experimentation (HTE) for electroorganic synthesis at a 15-microliter
scale. Two HTE modules are demonstrated, (1) the rapid
electrochemical reaction condition screening for a radical-radical
cross-coupling reaction on micro-fabricated interdigitated electrodes,
and (2) measurements of kinetics for mediated anodic oxidations
using the microliter-scale cyclic voltammetry. The presented modular
approach could be deployed for a range of other electroorganic
chemistry applications beyond the demonstrated functionalities.
Nonetheless, current efforts largely rely on manual operations
including reagent preparation, assembling electrochemical cell,
electroanalysis, workup, and product analysis. Herein, building on
our previous work with single-droplet microfluidic reaction
optimization systems,[20–22] we report an automated microfluidic
single-droplet screening and analysis platform for electroorganic
synthesis (Figure 1). During the automated experiment, the
computer-controlled liquid handler withdraws liquid from
designated vials to prepare a microfluidic droplet of the desired
reagent composition, and injects it into the sample loop (15 µL)
on a two-position six-port valve (Valve 2). A syringe filled with
pressurized nitrogen gas moves the droplet to the eChem flow cell
for either electrochemical reaction or electrochemical analysis.
Subsequently, the droplet is introduced into a HPLC sample loop,
triggering HPLC for analyzing the reaction outcome. After each
experiment, the system is cleaned multiple times with rinse
solvent droplets to avoid cross-contamination between two
consecutive runs. The location of the droplet within the
microfluidic system is tracked by phase sensors positioned at
essential points, such as the inlet and outlet of the eChem flow
cell.
Electroorganic synthesis, a synthesis method dating back to
the first discovery of anodic Kolbe decarboxylation in 1847,[1] has
recently received broad interests in the synthetic community. The
use of mild reaction conditions and electrons as the redox agent
brings prominent advantages such as improved process
sustainability and safety.[2–5] Moreover, the discovery of new
reactivities enabled by electrochemistry promotes further
adoption of this technique.[6] A number of exciting electrochemical
methodologies have recently been discovered, achieving
transformations that would be, otherwise, either challenging or
even impossible with conventional techniques.[7–12]
Nevertheless, electrochemical synthesis is still considered as
a niche technique with high entry barriers,[4,6,13] such as the
relative low experimentation throughput, attributed to the complex
electrochemistry setup, limiting the ability to quickly identify and
optimize new chemistries. Both academic groups and commercial
companies have devoted to developing electrochemistry-friendly
screening methodologies and standardized equipment to
streamline the adoption of electroorganic synthesis. Reaction
parallelization, as demonstrated by the Waldvogel group[14] and
the IKA company,[15] represents one avenue towards expediting
This fully automated electrochemistry platform offers distinct
advantages over conventional experimentation methods for
discovery and analysis of electrosynthesis:
1) Microliter sample volume per experiment allows generating
rich reaction information with minimal reagent consumption.
2) The streamlined reaction-analysis-cleaning experimental
cycle enables rapid automated operation after initial manual
reagent preparation.
1
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Figure 1. Schematics of the automated microfluidic platform for electrochemical reactions and analysis.
Compared with conventional synthesis, the additional reaction
parameters inherent in electroorganic synthesis, such as
electrolysis potential, create obstacles for efficient identification of
optimal conditions. Carrying out electrochemical reaction
screening in a microliter droplet, instead of milliliter vessels,
reduces the number of electrons needed to reach full conversion.
Consequently, if a comparable current is maintained, the reduced
electrolysis time brings the opportunity to expedite the screening.
A microfluidic electrochemical flow cell can offer excellent
conductivity by minimizing the gap between two parallel plate
electrodes,[23] but, the narrow channel depth leads to excessive
flow resistance creating challenges for smooth droplet
manipulation. Therefore, we developed a flow cell encapsulating
a micro-fabricated interdigitated electrodes (IDE) providing both
high cell conductivity and low flow resistance (Figure 2a). The
distance between two adjacent electrodes and the electrode width
are both 10 µm. This extremely small gap allows rapid inter-
electrode molecular diffusion, such that the reactive intermediates
can exchange between cathode and anode within 100 ms time.
injecting and withdrawing of the carrier gas to create recirculation
flow pattern within the droplet, ensuring mixing during the
electrochemical reaction.[28,29]
To demonstrate the platform’s capability of exploring the
reaction parameter space rapidly, we considered an
electrochemical redox-neutral radical-radical cross-coupling
reaction, α-amino C–H arylation. This reaction exemplifies a
broad category of single-electron transfer (SET) redox-neutral
chemistries that are typically realized via photocatalysis, but
recently demonstrated to be viable under electrochemical
conditions without the use of photocatalysts.[30] Mechanistically,
dicyanobenzene 1, an electron-deficient aryl nitrile, can undergo
SET reduction on cathode to form a persistent radical anion 4 at
E1/2 = –2.01 V (vs. Fc/Fc+). On the other hand, anodic oxidation of
amine 2 at Ep/2 = +0.50 V (vs. Fc/Fc+) giving a radical cation with
subsequent deprotonation of α-N C–H bond produces α-
aminoalkyl radical 5. Even though these two highly reactive
radical intermediates are generated separately on different
electrodes, the narrow inter-electrode distance within IDE allows
persistent radical 4 to diffuse rapidly across the gap and cross-
couple with the transient radical 5 to form arylation product 3.[30,31]
Conventionally, metal electrodes (e.g. platinum and gold) in
IDE are photolithographed on a glass or quartz substrate with
titanium or chromium as an adhesive layer.[24] However, those
metals tend to dissolve in the electrolyte under harsh anodic
conditions,[25,26] leading to limited lifetimes of the IDE. Instead, we
chose to use platinum silicide as the adhesive layer because of
its excellent electrochemical stability.[25,27] The pre-patterned
polysilicon (55 nm thick) and platinum metal (100 nm thick) layers
on an oxide coated p-type Si wafer were treated in a 7% H2 in N2
atmosphere at 300 °C to form the platinum silicide adhesive layer
(see Supporting Information for detailed fabrication procedure).
The excess platinum layer thickness ensured that the top IDE
surface of remained pure platinum metal (Figure 2a). The
fabricated IDE contained 146 cathode and anode pairs within a
24.7 mm2 area.
We set up an automated screening experiment to understand
the effect of reaction time and potential on the product yield. An
in-line HPLC directly analyzed 2 µL portion of the reacted droplets
giving chromatograms under different reaction conditions. When
increasing the reaction time under the same potential of 2.2 V, the
product peak grew as the reactant peak decreased (Figure 2d).
Regarding the reaction potentials, 1.8
V
was not
thermodynamically sufficient to initiate the radical generation.
After increasing the potential beyond 2.0 V, the reaction rate was
positively dependent on the overpotential applied, and a facile and
selective transformation was achieved under 2.6 V (Figure 2e).
Notably, obtaining such rich parametric information for this
electrochemical radical-radical cross-coupling reaction only
required around 300 µL reagents and 10 hours automated
platform runtime, saving significant amount of material and time
compared to the manual reaction condition screening.
The IDE chip was encapsulated in a microfluidic flow cell with
8 µL volume, and electric connections were realized using two
pairs of pogo pin connectors (Figure 2b). An oscillatory motion of
the reaction droplet in the flow cell was introduced by periodical
2
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Figure 2. (a) The micro-fabrication design of the IDE with a cross-section scanning electron microscope (SEM) image. (b) The fabricated IDE chip with SEM image
showing the electrode bands on the active electrode area, and the microfluidic flow cell for hosting the IDE chip. (c) The scheme for the electrochemical redox-
neutral α-amino arylation, and the reaction mechanism of the synergistic dual-electrode radical-radical cross-coupling reaction. (d) The HPLC chromatograms of
reacted droplets obtained at 2.2 V cell potential under various reaction times. (e) HPLC yields under various cell potentials and reaction times. (Mesitylene is used
as the internal standard.)
In addition to screening reaction conditions for optimal yield or
selectivity, implementing electroanalytical techniques on this
automated platform can facilitate rapid and material-efficient
kinetic measurements for gaining mechanistic understanding. To
demonstrate the concept of the automated electroanalysis, we
sought to develop a microliter-scale cyclic voltammetry (CV)
module to probe the electrochemical properties of analytes in the
droplet solution. CV being a technique relying on diffusion in a
semi-infinite static liquid solution[32–34] necessitates a flow cell
geometry satisfying the semi-infinite assumption, so that
previously derived analytical equations for CV applied. To achieve
this requirement while retaining a minimum volume of analyte
needed per analysis, a pocket was implemented directly in front
of the working electrode. The depth from the electrode surface to
the bottom of the pocket was designed to be 0.75 mm, which was
longer than the distance required for the semi-infinite assumption,
A representative mediated oxidation is the electrochemical
TEMPO-catalyzed alcohol oxidations under a mild oxidative
potential without additional oxidants added.[36,42,43] The TEMPO+
6 generated via anodic oxidation of TEMPOH 7 undergoes a two-
electron transfer reaction with the alcohol molecule in the solution
giving the carbonyl products (Figure 3b). The reaction rate of the
solution-phase oxidation is an essential factor in determining the
efficacy of this catalytic oxidation.[44] We demonstrated that
implementing the CV flow cell in the automated platform enabled
rapid measurements of kinetic constants for various alcohols with
minimum reagent consumption. Preparing droplets with various
alcohol concentration (ꢂꢃꢄꢅꢆꢇꢆꢄ) in the TEMPO solution resulted in
different catalytic currents that are linearly dependent on the
ꢂ
(Figure 3c). The catalytic current is the plateau current
ꢈ
ꢃꢄꢅꢆꢇꢆꢄ
after the peak on the cyclic voltammogram.[36,45] Primary alcohols
generally showed faster kinetics than the secondary alcohols, and
benzylic alcohols exhibited enhanced reaction rate compared to
aliphatic alcohols (Figure 3d).
6 ꢀꢁ ( ꢁ is the characteristic CV analysis time).[34] With this
√
geometry, the electroanalysis results obtained from the micro-
scale CV flow cell were in good agreement with those obtained
with a standard-size CV cell (see Supporting Information for
details).
In addition to the alcohol oxidation, the recently developed N-
hydroxytetrachlorophthalimide (Cl4NHPI) mediated allylic CH
oxidation was demonstrated to be a sustainable alternative to
conventional oxidation methods involving highly toxic reagents or
expensive catalysts.[7] With the interest of understanding this
newly developed catalytic system, we decided to measure the
kinetics of the hydrogen atom transfer (HAT) between anodically
generated Cl4NHPI radical 10 and allylic CH bond 13 on our
automated electroanalytic platform (Figure 3e). As shown in
Figure 3f, terminal and steric-hindered alkenes displayed
relatively low efficiency during the HAT step compared to other
cyclic or acyclic non-terminal alkenes.
Mediated electrochemical oxidations[35–39] form a class of
attractive transformations under mild conditions using catalytic
amount of mediators to avoid directly oxidizing molecules of
interest on the anode surface, which would typically require
excessive oxidation potential or risk passivating the electrode[40]
.
The mediator loses electrons on the anode followed by a
homogeneous chemical reaction step. Understanding the kinetics
of this homogeneous chemical step helps identify a suitable
substrate scope or facilitates reactor design for electrochemical
process development.[36,41]
3
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Figure 3. (a) The design and photo of the microliter-scale CV flow cell. Working electrode (WE): glassy carbon (GC); counter electrode (CE): platinum (Pt); pseudo-
reference electrode (RE): silver (Ag). (b) The reaction mechanism for TEMPO-catalyzed alcohol anodic oxidation. (c) Cyclic voltammograms of TEMPO-mediated
alcohol oxidation system for various 1-phenylethanol concentrations with 1 mM TEMPO, 0.45 M 1-methylimidazole (NMI), and 0.1 M tetrabutylammonium
perchlorate in MeCN. Blue line (no alcohol added) represents the reversible TEMPO oxidation cyclic voltammogram. Scan rate: 100 mV/s. Graph insert: linear
regression of catalytic current versus half-order of alcohol concentration. (d) Kinetic constants ꢉꢃꢄꢅꢆꢇꢆꢄ of TEMPO+ oxidizing seven different benzylic, aliphatic,
primary and secondary alcohols. (e) The reaction mechanism for Cl4NHPI-catalyzed allylic CH bond anodic oxidation. (f) Kinetic constants ꢉꢃꢄꢊꢋꢌꢋ of Cl4NHPI
radical 10 abstracting allylic hydrogen atoms from six different alkenes.
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The interdigitated electrode design allowed high current density
and efficient inter-electrode molecular transport, which facilitates
exploring optimal operation condition of electrochemical radical-
radical cross-coupling reactions. In addition, rapid measurements
of kinetics for two important mediated anodic oxidations were
achieved using a microliter-scale cyclic voltammetry flow cell. We
envision that this droplet-based electrochemical screening
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Entry for the Table of Contents
An automated electrochemistry screening platform based on a single-droplet microfluidic reactor enables multifunctional capabilities
for investigation of electroorganic synthesis. Reaction condition screening of an electrochemical radical-radical cross-coupling
reaction, and measurements of kinetics for two mediated anodic oxidation reactions are realized with fast turnover time and minimal
reagent consumption.
6
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