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A Hydrocarbon Cathode for Dual-Ion Batteries Ismael A Rodriguez Perez, Zelang Jian, Pieter K Waldenmaier, Joseph W Palmisano, Raghu Subash Chandrabose, Xingfeng Wang, Michael M Lerner, Rich G. Carter, and Xiulei Ji ACS Energy Lett., Just Accepted Manuscript • DOI: 10.1021/acsenergylett.6b00300 • Publication Date (Web): 05 Sep 2016 Downloaded from http://pubs.acs.org on September 7, 2016
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A Hydrocarbon Cathode for Dual-Ion Batteries
Ismael A. Rodríguez Pérez, Zelang Jian, Pieter K. Waldenmaier, Joseph W. Palmisano, Raghu Subash Chandrabose, Xingfeng Wang, Michael M. Lerner, Rich G. Carter* & Xiulei Ji* Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, United States
Corresponding Author
[email protected],
[email protected] Abstract: We have demonstrated, for the first time, a polycyclic aromatic hydrocarbon (PAH) crystalline and readily available coronene - exhibits highly reversible anion-storage properties. Conventional graphite anion insertion electrodes operate at potentials > 4.5 V vs Li+/Li, requiring additives and the use of ionic liquids. The coronene electrode shows flat plateaus at 4.2 V (charge) and 4.0 V (discharge) in a standard alkyl carbonate electrolyte and delivers a reversible discharge capacity of ~ 40 mA h g-1. Ex situ characterization reveals that coronene retains its crystalline structure and chemical bonding upon initial PF6- incorporation. Coronene-PF6 electrodes show impressive cycling stability: 92% capacity retention after 960 cycles. The discovery of the reversible anion-storage properties of coronene may open new avenues toward dual-ion batteries based on PAHs as electrodes.
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The paradigm of battery research has begun to shift to exploring electrode materials that are completely renewable, where such electrode materials ideally do not contain any metallic elements. Dual-ion batteries with graphite as both the anode and cathode have been investigated for more than two decades,1,2 although recently, a metal organic framework was used as a dual-ion battery cathode material as well.3 In contrast to cathodes in rocking-chair metal-ion batteries, those in dual-ion batteries operate by incorporation of anions.4 Anion intercalation into graphite, however, typically requires an operating potential above 4.5 V vs Li+/Li, often above the anodic stability limit of conventional electrolyte solvents.4–10 This limitation can be addressed by the use of expensive ionic liquids (ILs) as electrolytes.4,5,7,8,9,11–16 New storage chemistries will be required to enable dual-ion batteries that do not have to use ILs. The use of redox-active organic molecules as electrode materials in battery applications has attracted considerable attention due to their renewability without the use of any transition metal elements in the electrodes.17–21 To date, studies have been focused on molecules that contain carbonyl or anhydride functional groups as these groups can reversibly incorporate and dissociate alkali metal ions in a faradaic process.17,18,20,22–25 Moreover, organosulfur and nitroxide free radical compounds have been used as both n-type and p-type compounds for both cation and anion insertion, respectively.20,26,27 In this contribution, we show that coronene, a typical PAH molecular solid, functions as a highly reversible anion-insertion cathode and stores PF6- ions at a charge potential of 4.2 V vs Li+/Li. Commercial coronene powder (Sigma Aldrich) without any additional processing was added to carbon black and a binder and tested in coronene/Li half-cells, where lithium foil served as both the counter and reference electrode.
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Figure 1. A digital image of coronene solid with its molecular structure (top) and a monoclinic unit cell (space group: P21/a) with lattice constants of 16.1 Å (a), 4.7 Å (b), and 10.1 Å (c)28 (bottom). Figure 1 depicts the chemical structure and photograph of coronene as well as the unit cell of its crystal structure.28 Assembled only by van der Waals forces, coronene crystals exhibit a monoclinic structure (space group: P21/a) with no hydrogen crowding and lattice constants of 16.1 Å (a), 4.7 Å (b), and 10.1 Å (c). The much lower density of coronene (1.37 g cm-3) than graphite (2.26 g cm-3) facilitates the incorporation of bulky anions.29,30
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Figure 2. a) Charge/discharge potential profiles (at a current density of 20 mA g-1) with Roman numerals corresponding to different state of charge for ex situ XRD measurements. Pattern of point IV is indicated in red, which is corresponding to the fully charged electrode. b) Ex situ XRD patterns of coronene electrodes showing 2θ regions from 7-13º, 16-20º, and 20-30º to demonstrate peak formations and peak fading. The Roman numerals in a) and b) correspond to the same state of charge.
Figure 2a inset shows the first cycle charge/discharge potential profiles of the coronene electrode in electrolyte of LiPF6 (1.0 M) solvated in ethylene carbonate (EC) and diethyl carbonate (DEC) (v/v 1:1). While charging to 4.2 V, (hereafter all potentials are referenced to Li+/Li), a flat plateau is observed, indicating a two-phase oxidation reaction of coronene, thus forming carbocations. For charge compensation, PF6- as the only negative charge carrier available in the electrolyte must be incorporated into the structure, forming a charged state of the (coronene)x(PF6)y “salt”. During the following discharge, carbocation reduction exhibits a flat plateau at 4.0 V. Considering the semiconducting nature of coronene and its bulk particle size (Figure S1), the polarization is very small 4 ACS Paragon Plus Environment
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compared to that observed for graphite cathode in similar cells,[1,2,4-8] which suggests the more facile transport of PF6- in the coronene structure. The first charge capacity is 60.6 mA h g-1 (theoretically 89.2 mA h g-1 for one PF6- per coronene), corresponding to 0.68 PF6- incorporated per coronene molecule; while the following discharge capacity, 39.9 mA h g-1, gives a coulombic efficiency of 65.8% for the first cycle. We also investigated higher cutoff voltages (4.3, 4.4 and 4.5 V), which decreased the coulombic efficiencies to < 50% (Figure S2). Therefore, an upper cutoff of 4.2 V was maintained in subsequent tests. It is worth noting that control tests were done using pure carbon black as the electrode, showing an insignificant capacity of ~2.4 mA h g-1 and rapid fading, therefore not contributing to the reversible capacity of coronene. To better understand PF6- incorporation into the coronene electrodes, we investigated the evolving of the crystal structure and chemical bonding as a function of the state of charge (SOC). Figure 2a inset shows the selected points of SOC, at which ex situ measurements were performed. While the most intense (001) XRD peak remains unchanged upon charging, the (200) peak shifts from 2θ 11.7° to ~10.6º, indicating a structural expansion along a lattice direction by 0.08 Å (Figure 2a,b). The intensity of this shifted peak increases with further oxidation from point III to IV (Figure 2b). During the following discharge (from point V to VII) the intensity of this new peak decreases, showing a degree of reversibility of the structure change. Insertion of PF6- also causes a shift of the (111) peak after point IV (from 17.5° to 16.8°), which corresponds to an expansion of the (111) planes by 0.02 Å. During the following discharge, the (111) peak partially shifts back to its original angle. Considering these peak shifts, the sites for inserted PF6- ions can be tentatively proposed, as simultaneously between the (111) planes as well as the (200) planes (Figure S3). Anion intercalation also causes a marked decrease in coronene solid’s crystallinity as evidenced by the decrease of overall XRD peak intensity during charge, with only partial recovery upon discharge. However, the retention of the crystalline structure through the first cycle suggests that electrolyte solvent molecules do not co-insert.
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VII VI V IV III II I P.W. P C-H Stretch
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Figure 3. Ex situ FTIR spectra corresponding to different SOC, as indicated in Figure 2a inset, where P indicates the pristine electrode, and P.W. indicates a pristine electrode soaked in the 1 M electrolyte LiPF6 /EC:DEC (1:1). Ex situ Fourier-Transform Infrared (FTIR) spectra were used to characterize the possible changes in chemical bonding in coronene upon PF6- incorporation. Figure 3 shows two pristine samples: one (labelled as P) is a dry pristine electrode comprising coronene, C-45 (conducting carbon additive) and polyvinylidene fluoride (PVdF) and the other (labelled as P.W.) that has been soaked in the electrolyte of LiPF6 /EC:DEC (v/v 1:1). The low intensity signal at ~3000 cm-1 is assigned to the C-H stretch around coronene, while the signals at ~1800 cm-1 are assigned to the solvent C-O stretches. We attribute the region from 1500 to 1000 cm-1 to the C-C stretches in the aromatic rings of coronene and signals in the fingerprint region below 1000 cm-1 to C-H bending. Excluding electrolyte peaks, it is clear that no new peaks arise upon charging, suggesting that no new chemical bonds are formed during PF6- insertion. Ex situ nuclear magnetic resonance (NMR) performed upon the full charge also confirms the absence of new bonding in coronene (Figure S4). The unidentified peaks may be from the binder, PVdF or the electrolyte solution. Figure 4a shows the charge/discharge profiles for the 1st, 2nd, 3rd, and 10th cycles, where the plateau behavior is well maintained. Cyclic voltammetry (CV) results show high reversibility in the first 10 cycles (Figure 4b). Figure 4c shows the rate capability, where coronene is able to deliver ~21 mA h g-1, even at a high current density of 500 mA g-1, despite its low conductivity. The coronene electrode exhibits impressive long-term cyclability, where after 960+ cycles, the capacity retention is 92% 6 ACS Paragon Plus Environment
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(Figure 4d). Furthermore, coulombic efficiency in the long-term cycling study rises from 67.1% in the 1st cycle to 97.3.8% in the 100th cycle, 98.5% in the 300th cycle, and 98.6% in the 900th cycle. To understand the cycling behavior, we collected the charge/discharge potential profiles for the 50th, 100th, 200th, 300th, and 400th cycles, where we observe the disappearance of the plateaus (Figure S5). We attribute the conversion from the plateau behavior to a sloping one to the amorphization of coronene crystals over cycling. We hope to point out that coronene molecules in the crystallites are not covalently chained up to form rigid layers; thus, there could be exfoliation at the molecular scale instead of the scale of bulk crystal particles. Such structural uniqueness compared to inorganic crystals may explain its amorphization. The amorphization of coronene is supported by XRD patterns taken at different cycle numbers at a discharged state (Figure S6). c 1st Cycle 2nd Cycle 3rd Cycle 10th Cycle
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Figure 4. a) Charge/discharge potential profiles for the 1st, 2nd, 3rd, and 10th cycles. b) Cyclic voltammetry (CV) measurements for the 1st, 2nd, 3rd, and 10th cycles at a rate of 0.1 mV/s. c) Rate capability measurements, cycled 10 times at 20 mA g-1 for conditioning and 5 times each at 10, 20, 50, 100, 200, 500, and 100 mA g-1, followed by continued cycling (Figure 4d) at 20 mA g-1. d) Long-term cycling of the half-cell for over 960 cycles, along with coulombic efficiency (%).
Scanning electron microscopy (SEM) studies were conducted on coronene electrodes before and after insertion of PF6- anions (Figure S1). The macro-scale structural changes of coronene are evident, 7 ACS Paragon Plus Environment
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where the rod-like crystals of over 5 µm long and ~3 µm wide (Figure S1a) crack upon the first charge (Figure S1b) and turn into porous crystals after 400 cycles (Figure S1c). This explains why the capacity only drops in the first 50 cycles and is stable henceforth. These observations are confirmed by the structural changes, suggested by the X-ray diffraction (XRD) patterns (Figure S6) upon cycling. The surprisingly stable cycling of coronene may be associated with the formation of the more porous structure with a reduced strain for PF6- anion insertion. Solubility is, indeed, a critical issue of organic-based electrodes, particularly in non-aqueous electrolytes. Note that this issue is applicable not only to the pristine phase of the electrode before cycling but also to the evolving phases at varying SOC. The volume of work to comprehensively address this issue constitutes a separate project of its own. Currently, we are, in fact, working to reveal the detailed mass evolution of the coronene electrode and other organic molecular crystals as dual-ion cathode materials at different SOC, where the results will be reported in the future. The solubility properties of these molecular crystals will definitely serve as one of the selection rules on this family of materials for dual-ion battery purposes. Nevertheless, our available results have convinced us that the solubility of coronene in the used electrolyte is not a serious concern, at least not regarding to the electrochemical performance. The crystalline peaks of the ex situ XRD patterns, the associated shift of these peaks upon the intercalation of PF6- ions, and the flat-plateau potential profiles in the first cycle indicating a two-phase solid-state reaction collectively suggest a low solubility of coronene crystals and its derivative coronene-PF6 salts formed at different SOC in the used EC/DEC electrolyte. Additionally, the impressive cycling stability further confirms that coronene and its coronene-PF6 salts are of low solubility in the electrolyte, where there has been nearly no loss of electrode active mass into the electrolyte. Note that all the tests were conducted in flooded coin cells, where the electrolyte usage in this study would be much higher than the practical conditions, i.e., in pouch cells. In summary, we have demonstrated the first reported example of a PAH (coronene) cathode for dual ion batteries. Coronene offers a sizable advantage over traditional graphite cathodes due to its significantly lower operating potential (~ 4.2 V).
This enables the use of additive-free organic
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electrolytes and avoids the need for ionic liquids. Coulombic efficiencies, cycling, and the corresponding capacity retention all point to the promise of this new energy storage chemistry. Ongoing studies in our laboratories focus on realizing the full potential of PAH dual ion battery chemistry by exploring promising molecules. This discovery will bring new opportunities to energy storage solutions, where it points out that a library of PAH materials are waiting for exploration.
Experimental Methods Coronene powder (Sigma Aldrich > 97.0%) was mixed with carbon black (Super-P) and polyvinylidene fluoride (PVdF) at a 7:2:1 ratio. This mixture was then ground with N-methyl-2pyrrolidinone (NMP) solvent for ~ 30 min and was cast uniformly onto an aluminum foil current collector before being dried at 90 °C in an oven inside a fume hood for ~12 hrs. The dried coated aluminum foil was cut into electrodes of 5 mm in diameter, where the active mass loading is ~ 1.5 to 2.0 mg cm-2. The coin cells were assembled by using a coronene electrode (as prepared above) as the positive (working) electrode, and lithium metal as the negative (counter/reference) electrode.
A
polypropylene film was used as the separator, and 1 M LiPF6/EC:DEC (1:1) was used as the electrolyte. Cell assembly took place inside a glove box in an argon atmosphere. Rate performance of the electrodes was determined using galvanostatic charge/discharge (CD) tests performed at current densities of 10, 20, 50, 100, 200, and 500 mA g-1 on a MACCOR battery tester. Cyclic voltammetry (CV) studies were conducted at a scan rate of 0.1 mV/s, using a VMP3 BioLogic potentiostat. Both CD and CV studies were done by employing coin cells. To assess long-term reversibility of the material under study, cycling performance was tested in coin cells by a MACCOR battery tester at a current density of 20 mA g-1.
PTCDA structural simulations were modeled by software of
Visualization for Electronic and Structural Analysis (VESTA31) Version 3.
ASSOCIATED CONTENT
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Supporting Information Scanning electron microscopy imaging, cut-off voltage optimization, PF6- insertion site, Ex Situ NMR measurements, long cycling profiles, and X-ray patterns of structural evolution. AUTHOR INFORMATION Notes The authors declare no competing financial interests.
ACKNOWLEDGEMENT X. Ji is thankful for the financial supports from American Chemical Society Petroleum Research Fund, Grant Number: PRF # 55708-DNI10. The authors thank Professor Douglas A. Keszler for XRD measurements. We are also grateful to Ms. Teresa Sawyer and Dr. Peter Eschbach for their help in SEM measurements in OSU EM Facility, funded by National Science Foundation, Murdock Charitable Trust and Oregon Nanoscience and Micro- technologies Institute.
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