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ChemComm
DOI: 10.1039/C7CC03910G
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Fig. 3. Selected cyclic voltammograms of (a) 3a and (b) 3l. (c) Redox potentials of
1
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B. Reuillard, A. L. Goff, C. Agne`s, M. Holzinger, A. Zebda, C.
Gondran, K. Elouarzaki and S. Cosnier, Phys. Chem. Chem.
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R. D. Milton, “FAD-Dependent Glucose Dehydrogenase
Immobilization and Mediation Within a Naphthoquinone
Redox Polymer” Chapter 15, Shelley D. Minteer (ed.),
Enzyme Stabilization and Immobilization: Methods and
Protocols, Methods in Molecular Biology, vol. 1504, 193-
202.; R. D. Milton, D. P. Hickey, S. Abdellaoui, K. Lim, F. Wu,
,4-naphthoquinones and anthraquinone determined by CV.
naphthoquinones determined by the CV curves was depicted
in Fig. 3c. The redox potential of vitamin K 1a) shifted
towards negative potential after introducing of the ethyl group
3a) from -0.216 to -0.280 V vs Ag/AgCl. By increasing the
3
(
(
chain length of the alkyl group, the redox potential slightly
increased (3c and 3d). Introducing a phenyl group (3f) also
increased the redox potential whereas, an electron donating
B. Tana, S. D. Minteer, Chem. Sci. 2015, 6, 4867.
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or withdrawing group on the phenyl substituent (3g and 3h
)
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provides a negligible effect on the potential. Introducing a Cl
group (3k) further increased the potential. In contrast, an OH
group (3l) decreased the potential. All the compounds
produced in this research showed redox potential values
between that of 1,4-naphthoquinone (-0.14 V) and
anthraquinone (-0.49 V), being promising redox mediators in
enzymatic biofuel cells with a desirable potential range for
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FAD-GDH
system.
Furthermore,
substituted
1,4-
2
012, 23, 145; J. W. Lockner, D. D. Dixon, R. Risgaard, P. S.
naphthoquinones showed improved stability (Fig. S4).
Baran, Org. Lett., 2011, 13, 5628; Y. Fujiwara, V. Domingo, I.
B. Seiple, R. Gianatassio, M. D. Bel, P. S. Baran, J. Am. Chem.
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In summary, tuning the redox potential of 1,4-
naphthoquinones was achieved by introducing substituents at
the double bond of quinone moiety. Ag-catalysed alkylation in
homogeneous systems has been widely used for the
functionalization of 1,4-naphthoquinones. We have developed 10 K. Komeyama, T. Kashihara, K. Takaki, Tetrahedron Lett.,
a heterogeneous catalytic system with improved product yield
and demonstrated a possibility of catalyst recycling. Our
strategy in this manuscript is to determine optimal structures
by LUMO calculation with DFT method in order to accelerate
the research in the field of organic electrochemistry and
bioelectrocatalysis. Currently, we are optimizing the
parameters for the calculation of redox potential of candidate
molecules with improved correlation since the LUMO level
does not yet exactly correspond to the redox potential (Table
S6 and Fig. S5). Improving the accuracy of calculations with
experimental matching would be extremely useful in future
material design and fabrication.
2013, 54, 1084.
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This work was financially supported by JST SICORP, ANR (ANR-
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−
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Notes and references
2
−
§
When applying for glucose biofuel cells, the redox potential of
−
a mediator molecule must be higher than -0.36 V, where
oxidation of glucose occurs on glucose oxidase. See Fig S1 in
Supporting Information.
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§§ Leaching of Ag was confirmed by adding Cl (aq.HCl) to the
reaction mixture. White suspension (AgCl) was observed.
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