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doi.org/10.1002/anie.202304366

Solid-state Air Batteries

All-Solid-State Rechargeable Air Batteries Using
Dihydroxybenzoquinone and Its Polymer as the Negative Electrode
Makoto Yonenaga, Yusuke Kaiwa, Kouki Oka, Kenichi Oyaizu, and Kenji Miyatake*

Abstract: A proof-of-concept study was conducted on an
all-solid-state rechargeable air battery (SSAB) using
redox-active 2,5-dihydroxy-1,4-benzoquinone (DHBQ)
and its polymer (PDBM) and a proton-conductive
polymer (Nafion). DHBQ functioned well in the redox
reaction with the solid Nafion ionomer at 0.47 and0.57 V vs. RHE, similar to that in acid aqueous solution.
The resulting air battery exhibited an open circuit
voltage of 0.80 V and a discharge capacity of
29.7 mAh gDHBQ 1 at a constant current density(1 mA cm 2). With PDBM, the discharge capacity wasmuch higher, 176.1 mAh gPDBM 1, because of the improved utilization of the redox-active moieties. In therate characteristics of the SSAB-PDBM, the coulombic
efficiency was 84 % at 4 C, which decreased to 66 % at
101 C. In a charge/discharge cycle test, the capacity
remaining after 30 cycles was 44 %, which was able to besignificantly improved, to 78 %, by tuning the Nafion
composition in the negative electrode.

Batteries with high capacity, durability, environmental

compatibility, and low cost are in great demand.[1] Comparedto the existing, commercially available secondary batteries,
including lead-acid batteries, nickel-cadmium batteries, andlithium-ion batteries,[2] air batteries using oxygen fromambient air as an active material in the positive electrodehave generated great interest due to their potentially high[*] M. Yonenaga, Prof. Dr. K. Miyatake
Clean Energy research Center, Fuel Cell Nanomaterials Center,
University of Yamanashi
4 Takeda, Kofu, Yamanashi 400-8510 (Japan)
E-mail: miyatake@yamanashi.ac.jp
Y. Kaiwa, Dr. K. Oka, Prof. Dr. K. Oyaizu, Prof. Dr. K. Miyatake
Department of Applied Chemistry, Research Institute for Scienceand Engineering, Waseda University
Tokyo 169-8555 (Japan)
Dr. K. Oka
Current address: Center for Future Innovation (CFI) and Department of Applied Chemistry, Graduate School of Engineering, Osaka
University
Osaka 565-0871 (Japan)© 2023 The Authors. Angewandte Chemie International Edition
published by Wiley-VCH GmbH. This is an open access article under
the terms of the Creative Commons Attribution Non-Commercial
License, which permits use, distribution and reproduction in any
medium, provided the original work is properly cited and is not used
for commercial purposes.
Angew. Chem. Int. Ed. 2023, e202304366 (1 of 5)energy density.[3] For typical air batteries, metals such as Li,
Ca, Al, Mg, Cd, and Zn have been used as active materials
for the negative electrodes. Among these, Li-air and Zn-air
batteries have been most actively studied.[4] For example, arecent study revealed that a rechargeable Li-air battery
using GaOx/LixLM/LiM exhibited a maximum capacity ofca. 1100 mAh g 1, a coulombic efficiency of 100 %, and acapacity of 70 % remaining after 350 charge/discharge cycles
at 0.2 C.[5] A rechargeable Zn-air battery using a ZnO/C
negative electrode exhibited a maximum discharge capacityof 207 mAh g 1 and a coulombic efficiency of 83 % without
dendrite formation.[6]In most cases, rechargeable metal-air batteries utilize
liquid electrolytes (in the above cases, lithium salts indimethoxyethane and KOH aqueous solution, respectively)
accompanied by inherent issues of high ohmic resistance,leaching and/or combustion. Furthermore, metal-air batteries often have to use protective films and separators to
mitigate the dendrite formation and growth peculiar tometal materials and to avoid exposure to the atmosphere.[4, 7]
Recently, in place of metals, redox-active organic
molecules have also been investigated for use as negativeelectrodes, in which protons or hydroxide ions participate in
the redox reactions.[8] In those previous studies, quinone- oramine-based molecules or polymers were used with acidic orbasic aqueous solution. The resulting rechargeable airbatteries exhibited high performance, close to the theoretical maximum capacity. The maximum capacity could behigher than ca. 200 mAh g 1 with > 60 000 charge/discharge
cycle capability.[9] The use of redox-active organic molecules
releases rechargeable air batteries from the problems
associated with metals, including dendrite formation andnegative environmental impact. Nevertheless, these types ofbatteries still use liquid electrolytes, with their attendantsafety concerns.
In the present paper, we took on the challenge of
constructing an all-solid-state rechargeable air battery(SSAB) consisting of redox-active organic molecules and a
proton-conductive polymer electrolyte (Nafion). To the bestof our knowledge, there have not been such air batteries
using organic electrodes and acidic polymer without liquid
electrolyte. 2,5-Dihydroxy-1,4-benzoquinone (DHBQ) andpoly(2,5-dihydroxy-1,4-benzoquinone-3,6-methylene)(PDBM) were chosen as the negative electrode active
materials since they exhibit stable and reversible redox
reaction in acidic conditions. Nafion is the most common
proton-conductive membrane, with a conductivity of up to
10 1 S cm 1 in humidified air. Charge/discharge performance,© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbHrate characteristics, and cyclability of the SSABs were
investigated.
Figure 1 depicts detailed configuration of the all solidstate air battery used in the present study (see Figure S1 forphotos). For the oxygen electrode, a gas diffusion electrode(GDE) attached to the membrane, typically used forpolymer electrolyte membrane fuel cells (PEMFCs), wasadopted. A minor difference was the separator made ofplatinum-coated titanium plate for anti-corrosion at highpotential. The negative electrode containing the redox active
organic molecules was directly coated onto the protonconductive solid polymer electrolyte (Nafion) membrane.
Another GDE with reference hydrogen electrode (RHE)
was attached onto the Nafion membrane through the gas
diffusion layer to measure each electrode potential, independently.
Figure 2 shows the CV curves of the negative electrodes
with solid polymer electrolyte in SSAB-DHBQ and SSABPDBM. DHBQ is known to exhibit reversible redox peak at
0.2 V vs. Ag/AgCl (or ca. 0.46 V vs. RHE) in sulfuric acidaqueous solution (pH = 1) based on two-electron hydroquinone/quinone redox reaction. In the present case, DHBQ
exhibited a set of two broad peaks at ca. 0.47 and 0.57 V vs
RHE, indicative of two-step one-electron redox reaction
with the solid electrolyte (Figure 2a). From the electriccharge of the oxidation peak, the utilization of DHBQ (=Angewandte
Chemieelectric charge divided by the moles of DHBQ loaded in theelectrode assuming the two-electron redox reaction) was
merely 5.7 %. With the polymeric (PDBM) electrode,similar but more distinct redox peaks were observed atsimilar potentials (Figure 2b), where the utilization of
PDBM was as high as 45.8 %. Much higher utilization withPDBM than that with DHBQ is probably because thepolymeric PDBM would have better affinity with thepolymeric proton conductive electrolyte achieving betterconnected and more efficient triple phase boundary with theelectron conductive carbon in the electrode (this issue isdiscussed below with Figure 4c and d).
Figure 3 shows the configuration and cell reactions of
SSAB-DHBQ. In order to minimize the overpotential at theoxygen electrode and the ohmic resistance of Nafion
membrane, the system was maintained at 100 % relative
humidity (RH) during the charge/discharge experiments.
Figure 4a shows charging curves of SSAB-DHBQ and
SSAB-PDBM cells at a constant current density of
0.227 mA cm 2 which corresponded to 7.63 C for SSABDHBQ and 1.09 C for SSAB-PDBM, respectively. During
the charging, the potential of the oxygen electrode increased
rapidly from ca. 0.70 V to ca. 0.90 V and then gradually toover 1.10 V, where the water oxidation reaction took place
to produce oxygen (Figure 4b). Accordingly, the potential of
the redox active organic electrode decreased from ca. 0.70 V
to 0.1 V reducing DHBQ and PDBM (Figure 4c). The
charging time was much longer for SSAB-PDBM than for
SSAB-DHBQ. The charge capacity was 29.7 mAh gDHBQ 1
for SSAB-DHBQ and 208 mAh gPDBM 1 for SSAB-PDBM,
respectively. Based on the loading amount of the redox
active molecules in the electrode, the utilization of DHBQ
and PDBM for the charging was 8 % and 59 %, respectively,
assuming the two-electron redox reaction. It is noted the

Figure 1. Configuration of the all solid-state air battery containing
redox-active organic negative electrode, GDEs (for oxygen electrodeand RHE), and solid polymer electrolyte (Nafion) membrane. GDE andGDL refer to gas diffusion electrode and gas diffusion layer,
respectively.

Figure 2. Cyclic voltammograms (CVs) of redox-active organic negativeelectrodes in a) SSAB-DHBQ and b) SSAB-PDBM before charge/
discharge cycles (solid line) and after charge/discharge cycles (dashedline). The CVs were obtained at 40 °C at a scan rate of 20 mV s 1
supplying fully humidified hydrogen to the positive electrode at
100 ml min 1 and no gases to the negative electrode, respectively.
Angew. Chem. Int. Ed. 2023, e202304366 (2 of 5)

Figure 3. Simplified cell configuration and cell reactions of SSABDHBQ. The temperature and humidity were set at 40 °C and 100 % RH,
respectively, throughout the experiment.

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Figure 4. Charging curves of SSAB-DHBQ and SSAB-PDBM at
0.227 mA cm 2. a) cell voltage, b) oxygen electrode potential, c) redox
active electrode potential and d) ohmic resistance. The curves wereobtained at 40 °C and 100 % RH.

redox active polymer, PDBM, participated much more in
the redox reaction than the small molecule DHBQ presumably because PDBM and proton-conductive polymer Nafion
would have formed better-connected ionic and electronic
channels with carbon. The hypothesis was supported bysmaller ohmic resistance of SSAB-PDBM (0.22 Ω cm2) thanthat of SSAB-DHBQ (0.51 Ω cm2) (Figure 4d).
When discharging, the cell voltage was initially ca.
0.80 V (OCV) and decreased with time at a constant current
density of 1 mA cm 2 (Figure 5a). The discharging time wasmuch longer for SSAB-PDBM than for SSAB-DHBQ,
similar to the charging time. For SSAB-DHBQ, since theoxygen electrode potential was nearly constant at 0.89 V
after the initial drop from 1.02 V (Figure 5b), the cell voltage
was mostly dominated by the DHBQ electrode. In fact, theFigure 5. Discharging curves of SSAB-DHBQ and SSAB-PDBM at
1 mA cm 2. a) cell voltage, b) oxygen electrode potential, c) redox active
electrode potential and d) ohmic resistance. The curves were obtained
at 40 °C and 100 % RH.
Angew. Chem. Int. Ed. 2023, e202304366 (3 of 5)

Angewandte
Chemiepotential of the DHBQ electrode increased from 0.24 V to
0.89 V with the discharging time (Figure 5c). For SSABPDBM, although both electrode potentials behaved similarly, the oxygen electrode became constant at somewhat
lower potential (ca. 0.76 V). The increase in the negativeelectrode was much smaller for PDBM than for DHBQ.
The ohmic resistance was constant for both cells during
discharging at the same values as that during the charging(Figure 5d).
Then, the rate characteristic of the SSAB-PDBM wasinvestigated. Figures 6 shows discharging curves at different
rate, where the charging rate was constant at 4 C(0.705 mA cm 2) for all cases (see Figure S2 for the charging
curves). The OCV was ca. 0.8 V. At any discharging ratefrom 4 C to 101 C, the initial loss in the cell voltage from
OCV to ca. 0.5 V was similar (Figure 6a). The discharge
capacity was 146.1 mAh gPDBM 1 at 4 C and decreased withthe discharging rate to 115.6 mAh gPDBM 1 at 101 C. The
oxygen electrode potential decreased faster at higher
discharging rate (Figure 6b) and the redox active electrodepotential was much less dependent on the discharging rate
(Figure 6c), indicating that the oxygen reduction reaction
became sluggish probably because the product water
became liquid at 40 °C and was not effectively exhausted
from the electrode at high discharging rate (so-called flooding) resulting in the insufficient supply of oxygen. The
coulombic efficiency was substantially high (84 %) at 4 C
and decreased gradually to 66 % at 101 C without significant
drop (Figure 6d). Since the oxygen electrode was exposed tohigh potential (> 1.1 V) during the charging, the Pt/C
catalysts might have degraded to cause deteriorated catalytic
activity.
Cycle test of SSAB-PDBM was performed at 15 C
(2.268 mA cm 2). As shown in Figure 7a and Figure 8, thedischarge capacity was initially 109.6 mAh gPDBM 1 anddecreased to 47.9 mAh gPDBM 1 after 30 cycles where the

Figure 6. Discharging curves and coulombic efficiency of SSAB-PDBM
at 4 (0.705), 10(1.763), 20(3.528), 40(7.054), 61(10.58), 81(14.11), and
101 (17.63) C (mA cm 2). a) cell voltage, b) oxygen electrode potential,c) redox active electrode potential and d) coulombic efficiency. The
curves were obtained at 40 °C and 100 % RH.

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Angewandte
ChemieFigure 7. Discharging curves of SSAB-PDBM during cycle test at 15 C
(2.268 mA cm 2). a) cell voltage, b) oxygen electrode potential andc) redox active electrode potential. The curves were obtained at 40 °C
and 100 % RH.

Figure 9. Discharging curves of SSAB-PDBM (I/C = 2.0) during cycle
test at 15 C (2.967 mA cm 2). a) cell voltage, b) oxygen electrodepotential and c) redox active electrode potential. The curves wereobtained at 40 °C and 100 % RH.

Figure 8. Change of the discharge capacity (black) and Coulombic
efficiency (red) of SSAB-PDBM at 15 C (2.268 mA cm 2) during thecycle test.

Figure 10. Change of the discharge capacity (black) and Coulombic
efficiency (red) of SSAB-PDBM (I/C = 2.0) at 15 C (2.967 mA cm 2)during the cycle test.

capacity remaining was 44 % (see Figure S3 for the charging
curves). The decrease of the capacity was due both to theoxygen (Figure 7b) and PDBM electrodes (Figure 7c). The
oxygen electrode was probably deteriorated during therepeated charging where the potential exceeded over 1.50 V
vs. RHE causing the corrosion of the carbon support. To
identify the cause of the performance loss in the PDBM
electrode, the CV curve was measured after 30 cycles. As
shown in Figure 2b, the redox peaks of the PDBM became
smaller with the utilization of PDBM from 46 % (initial) to
13 % (after 30 cycles). Some PDBM molecules might havebecome electrochemically inactive probably because ofleaching out from the triple phase boundary during the cycle
tests since PDBM is a highly hydrophilic molecule with fourhydroxy groups per phenylene unit in the reduced form.
Although the capacity decreased, the coulombic efficiency
was initially 77 % and was kept relatively high at 61 % after
30 cycles (Figure 8), indicating that the remaining PDBM
molecules participated well in the redox reactions.
To improve cyclability of the SSAB-PDBM, the mass
ratio of Nafion ionomer to the carbon (I/C) in the PDBM
electrode was increased from 0.7 to 2.0 aiming at making
more PDBM electrochemically active and preserving thepolymer in the active site for longer time. As shown in
Figures 9a and 10, the initial discharge capacity was

183.8 mAh gPDBM 1 and much higher than that of the abovementioned cell with I/C = 0.7 (see Figure S4 for the charging
curves).
The
discharge
capacity
decreasedto143.4 mAh gPDBM 1 after 30 cycles with capacity remaining of
78 % which was also much higher than that (44 %) of thecell with I/C = 0.7. Although the oxygen electrode wasdeteriorated similarly during the cycle test (Figure 9b), the
PDBM electrode was rather stable for 30 cycles with minorchanges in the discharging curves (Figure 9c). The coulombic efficiency was initially 83 % and decreased to 64 %(Figure 10), similar to that of the cell with I/C = 0.7. The
results suggest that the increased Nafion ionomer in the
PDBM electrode was effective in improving the performance and durability of the negative electrode and accordingly, those of the SSAB-PDBM. After the test, the catalyst
coated membrane was recovered from the cell and subjectedto the SEM analyses. The surface images of the PDBM
electrode and the cross-sectional images did not provide
evidences of structural and morphological degradation (Figure S5).
As a conclusion, we have successfully operated an allsolid-state rechargeable air battery (SSAB) composed ofredox-active organic molecules as the negative electrode, aproton-conductive polymer as the electrolyte, and an oxygen-reducing, diffusion-type positive electrode. Unlike typi-

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cal air batteries using a metallic negative electrode and anorganic liquid electrolyte, the SSAB did not deteriorate in
the presence of water and oxygen (on the contrary, water isessential for the redox reaction and proton conduction).
Compared to the small redox-active molecule (2,5-dihydroxy-1,4-benzoquinone (DHBQ)), its polymeric counterpart (PDBM) functioned better as the negative electrode,with higher utilization. Accordingly, the respective discharge
capacities at a constant current density (1 mA cm 2) were
29.7 mAh gDHBQ 1 for SSAB-DHBQ and 176.1 mAh gPDBM 1
for SSAB-PDBM. In examining the rate characteristics of
the SSAB-PDBM, even though the PDBM electrodepotential was not dependent on the discharge rate, theoxygen electrode potential decreased faster with increasing
discharge rate. Thus, the coulombic efficiency gradually
decreased from 84 % at 4 C to 66 % at 101 C. The charge/
discharge cyclability of the SSAB-PDBM was not verysatisfactory, with a discharge capacity of only 44 % remaining after 30 cycles. The remaining capacity was able to besignificantly improved, to 78 %, by tuning the negativeelectrode composition (by increasing the proton-conductive
polymer content). Thus, while the present study proved theconcept of the SSAB experimentally, its performance wasstill somewhat primitive. The instability of the oxygenreducing diffusion electrode and the relatively high redox
potential of the organic molecules are priority issues that weplan to address in our near-future agenda.

Acknowledgements
This work was partly supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT),
Japan, through Grants-in-Aid for Scientific Research(18H05515, 23H02058) and MEXT Program: Data Creationand Utilization Type Material Research and Development
Project (JPMXP1122712807), and JKA promotion funds
from AUTORACE.

Conflict of Interest
The authors declare no conflict of interest.

Angew. Chem. Int. Ed. 2023, e202304366 (5 of 5)

Angewandte
ChemieData Availability Statement
The data that support the findings of this study are available
from the corresponding author upon reasonable request.
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Manuscript received: March 27, 2023
Accepted manuscript online: May 2, 2023
Version of record online: ■■■, ■■■■© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

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Communications

Angewandte
ChemieCommunications
Solid-state Air Batteries
M. Yonenaga, Y. Kaiwa, K. Oka, K. Oyaizu,
K. Miyatake*e202304366
All-Solid-State Rechargeable Air Batteries
Using Dihydroxybenzoquinone and Its Polymer as the Negative ElectrodeAngew. Chem. Int. Ed. 2023, e202304366

All-solid-state rechargeable air battery
has been achieved using a redox-active
organic molecule (dihydroxybenzoquinone, DHBQ) as the negative electrodeactive material and a proton exchange
membrane as the electrolyte. The highredox activity of DHBQ with the polymer
electrolyte made the concept of thedevice possible and furthermore, use ofpolymeric DHBQ improved significantly
the discharge capacity with reasonablecyclability.

© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

15213773, 0, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/anie.202304366 by University Of Yamanashi, Wiley Online Library on [16/05/2023]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License

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