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Environmentally Sustainable Aluminiumcoordinated Poly(tetrahydroxybenzoquinone) as a Promising Cathode for Sodium Ion Batteries Hee Joong Kim, Youngjin Kim, Jimin Shim, Kyung Hwa Jung, Min Soo Jung, Hanseul Kim, Jong-Chan Lee, and Kyu Tae Lee ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.7b13911 • Publication Date (Web): 03 Jan 2018 Downloaded from http://pubs.acs.org on January 4, 2018

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ACS Applied Materials & Interfaces

Environmentally Sustainable Aluminiumcoordinated Poly(tetrahydroxybenzoquinone) as a Promising Cathode for Sodium Ion Batteries Hee Joong Kim,†,‡ Youngjin Kim,§,‡ Jimin Shim, Kyung Hwa Jung, Min Soo Jung, Hanseul Kim, Jong-Chan Lee*, and Kyu Tae Lee* School of Chemical and Biological Engineering and Institute of Chemical Process, Seoul National University, 599 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea, KEYWORDS: Coordination polymer, Organic compound, Benzoquinone, Aluminum, Sodium ion battery, Cathode

ABSTRACT

Na-ion batteries are attractive as an alternative to Li-ion batteries because of their lower cost than Li-ion batteries. Organic compounds have been considered as promising electrode materials due to their environmental friendliness and molecular diversity. Herein, aluminum-coordinated poly(tetrahydroxybenzoquinone) (P(THBQ-Al)), one of the coordination polymers, is introduced for the first time as a promising cathode for Na-ion batteries. P(THBQ-Al) is synthesized

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through a facile coordination reaction between benzoquinonedihydroxydiolate (C6O6H22-) and Al3+ as ligands and complex metal-ions, respectively. Tetrahydroxybenzoquinone is environmentally sustainable because it can be obtained from natural resources such as orange peels. Benzoquinonedihydroxydiolate also contributes to delivering high reversible capacity because each benzoquinonedihydroxydiolate unit is capable of two electron reactions through the sodiation of its conjugated carbonyl groups. Electrochemically inactive Al3+ improves the structural stability of P(THBQ-Al) during cycling because of no change in its oxidation state. Moreover, P(THBQ-Al) is thermally stable and insoluble in non-aqueous electrolytes. These result in excellent electrochemical performance including a high reversible capacity of 113 mA h g-1 and stable cycle performance with negligible capacity fading over 100 cycles. Moreover, the reaction mechanism of P(THBQ-Al) is clarified through ex situ XPS and IR analyses, in which the reversible sodiation of C=O into C−O−Na is observed.

INTRODUCTION Na-ion batteries have received much attention as an attractive alternative to Li-ion batteries because they are potentially low in cost per energy.1-5 In addition, the insertion chemistry of Naion batteries is similar to that of Li-ion batteries because both use a monovalent charge carrier, such as Li+ and Na+.6-10 This similarity enabled us to develop various electrode materials for sodium-ion batteries in a short period of time using a database of electrode materials investigated in Li-ion batteries. For example, graphite,11-13 hard carbon,14-17 alloys,18-21 phosphorus,22-25 metal oxides,26-28 polyanion materials,29-31 and organic compounds32-53 have been examined as electrode materials for Na-ion batteries and exhibited promising electrochemical performances. Among them, organic compounds, including organic free radicals,32 organosulfur,33 and organic


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carbonyl34-43, 45 compounds have recently been considered promising electrode materials due to their environmental friendliness, molecular diversity, and good electrochemical performance.54-56 In particular, quinone derivatives such as benzoquinone (BQ),44-46 anthraquinone (AQ),47-49 phenanthraquinone (PQ),50-51 naphthoquinone (NQ)52 are attractive as a cathode because of their high theoretical capacity (approximately 600 mA h g−1) and high redox potential. However, many quinone derivatives have challenging issues, including their poor cycle performance due to the dissolution of electrode materials in an electrolyte and low thermal stability.44-47, 54, 57-59 Various strategies have been introduced to improve these poor properties. For example, single organic molecules were incorporated into porous carbons through a π-π interaction between aromatic compounds and carbon.50, 59 However, organic components in the composites were eventually dissolved during cycling, although their initial forms were insoluble. Organic salts and polymers were also investigated because they are intrinsically insoluble in the electrolyte.45 However, most were structurally unstable, thus leading to structural deformation during cycling. This resulted in the degradation of electrode materials. Recently, metal-organic coordination polymers (CPs) including metal-organic frameworks (MOFs) and porous coordination polymers (PCPs) have received considerable attention for the synthesis of supramolecular polymers, nanoparticles, and cross-linked hydrogels.60-65 Coordination-driven polymerization is attractive because of its simple and facile synthesis in which building blocks are easily constructed through coordination between metals and organic ligands. They are also structurally and thermally stable. Moreover, their solubility in nonaqueous solvents is controllable, depending on the types of ligands and complex metal-ions.61 These properties are advantageous for electrode materials in Na-ion batteries. Therefore, we introduce the aluminum-coordinated poly(tetrahydroxybenzoquinone) (P(THBQ-Al)), one of the


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coordination polymers, for the first time as a promising cathode material for Na-ion batteries. Benzoquinonedihydroxydiolate (C6O6H22−) and aluminum cation (Al3+) were selected as ligands and complex metal ions, respectively, for the preparation of a coordination polymer. Benzoquinonedihydroxydiolate has a stable phenolic ligand, thus leading to the formation of diverse stable chelating complexes. Benzoquinonedihydroxydiolate is also environmentally friendly and sustainable because it can be obtained from glyoxal or myo-inositol, widely present in natural resources, such as orange peels, grapes, and plant leaves.44,

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Moreover, each

benzoquinone unit in the polymer is capable of two electron reactions through the sodiation and desodiation of its conjugated carbonyl groups, resulting in a high reversible capacity. Aluminum cation (Al3+) is a complex metal ion that is suitable for electrode materials. Although various metal cations can form coordination polymers with benzoquinonedihydroxydiolate,64,

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electrochemically inert metal cations that are not involved in the redox reaction are more promising in terms of their structural stability. Specifically, transition metal cations, such as iron, nickel and cobalt are involved in the redox reaction, in which their oxidation states change during charging and discharging.68-71 This causes repetitive breakage and/or the rearrangement of the coordination bonds during cycling, leading to structural deformation. In contrast to the electrochemically active metal cations, the coordination bonds of electrochemically inert metal cations, such as Al3+, are not deformed during charging and discharging because the oxidation state of Al3+ is not changed during cycling. This results in improved structural stability. Owing to these properties of benzoquinonedihydroxydiolate and Al3+ in the coordination polymer, P(THBQ-Al) exhibited excellent electrochemical performance, including a high reversible capacity of 113 mA h g-1 and stable cycle performance with a negligible capacity fading over 100 cycles. Moreover, we clarified the reaction mechanism of P(THBQ-Al) through ex situ XPS


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and IR analyses, in which the reversible transition between C=O and C−O−Na was observed during discharging and charging.

EXPERIMENTAL SECTION Materials. Tetrahydroxybenzoquinone (THBQ, >96 %) and aluminum chloride (AlCl3, >98 %) were obtained from Tokyo Chemical Industry (TCI). Poly(vinylidene fluoride) (PVdF), Nmethyl-2-pyrrolidone (NMP) (anhydrous), tetraethylene glycol dimethyl ether (TEGDME, >98 %), sodium perchlorate (NaClO4, >98 %), and sodium hydroxide (NaOH, >98 %) were obtained from Sigma-Aldrich and used without any purification. Conductive carbon black (Super P, Alfa Aesar, A Johnson Matthey Company) was dried at 60 oC in a vacuum over 24 hours before use. Deionized (DI) water with a resistivity of 18.3 mΩ cm was obtained from a water purification system (Synergy, Millipore, USA). Synthesis of Poly(THBQ-Aluminum) (P(THBQ-Al)). 2.32 mmol of AlCl3 (0.31 g) was added to the aqueous solution of THBQ (2.32 mmol, 0.4 g). The mixture was vigorously stirred at room temperature with N2 blowing. After stirring for 10 min, 60 mL of 1 M NaOH solution was added with stirring. A dark-brown solid was precipitated. The filtrated product, P(THBQ-Al), was washed with ethanol, methanol, and acetone, and then dried in a vacuum. Yield: 0.64 g (62.7 %). Electrochemical Characterization. P(THBQ-Al) powders were mixed with carbon black (CB, Super P) and poly(vinylidene fluoride) (PVdF) in NMP in a 6:2:2 weight ratio. The slurry was casted onto an aluminum current collector. The electrodes were dried at 120 oC in a vacuum over 8 hours. In the case of THBQ, electrodes were prepared with a 3:2:5 weight ratio (THBQ: CB: PVdF). The loading amounts of electrode materials were approximately 1 mg cm−2. The electrochemical performance was evaluated using 2032 coin cells with a Na metal anode and 1


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M NaClO4 in a TEGDME electrolyte solution. The galvanostatic experiments were performed with the current density of 20 mA g−1 (ca. 0.2 C) at 30 oC. To examine the dissolution of active materials in the electrolyte, 1 mg of active materials was stored in 1 mL of the electrolyte for a week. Material Characterization. Coordination chemistry in P(THBQ-Al) was investigated by X-ray photon electron spectroscopy (XPS, PHI-1600) using Mg Kα (1254.0 eV) as a radiation source. Survey spectrum was collected over a range of 0‒1100 eV, followed by a high resolution scan of the C 1s, O1s, and Al 2p region. The coordination reaction between hydroxyl groups and aluminum cation was confirmed by Fourier-transform infrared spectroscopy (FT-IR, Nicolet 6700, Thermo Scientific). The morphologies of THBQ and P(THBQ-Al) were examined using a field emission scanning electron microscope (FESEM, JSM-6701F, JEOL). The crystal structures and thermal properties of THBQ and P(THBQ-Al) were investigated using powder Xray diffractometry (D8 Advance, Bruker) and thermal gravimetric analysis (TGA, Q-5000 IR, TA Instruments), respectively. TGA was operated at the heating rate of 10 oC min−1 in N2 atmosphere. For ex situ analyses, coin cells were disassembled in an argon-filled glove box. Then, the collected electrodes were washed with dimethyl carbonate (DMC) and sealed in a pouch to inhibit their exposure to ambient air. The sealed pouches were opened just before XPS and FT-IR spectroscopy measurements.

RESULTS AND DISCUSSION Figure 1a demonstrates the facile synthesis of P(THBQ-Al) through a coordination driven selfassembly of phenolic ligand (Tetrahydroxybenzoquinone (THBQ) anion) and metal ion (Al3+ cation). As 1 M NaOH aqueous solution was added to the aqueous solution of THBQ and AlCl3


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mixtures, phenol groups in THBQ were deprotonated, forming a benzoquinonedihydroxydiolate (C6O6H22−). The O− with a lone pair in the ligand were then expected to be coordinated with Al3+ through coordination bonds,72-75 leading to the precipitation of P(THBQ-Al) powders. Figure 2a shows the Fourier transform infrared spectroscopy (FT-IR) spectra of THBQ and P(THBQ-Al). As THBQ was converted into P(THBQ-Al), the intensity of hydroxyl vibrational peaks at 3360 and 3544 cm−1 substantially decreased, whereas a new characteristic peak of Al-O bonding at 1508 cm−1 appeared.61 This suggests that THBQ was polymerized into P(THBQ-Al) through the coordination of C6O6H22− and Al3+ ions. The formation of P(THBQ-Al) was further supported by the Al 2p X-ray photoelectron spectroscopy (XPS) spectrum of P(THBQ-Al). As shown in Figure 2b, the Al 2p XPS peak was observed at 74.4 eV, corresponding to the Al-O bonding.76 The XRD patterns of THBQ and P(THBQ-Al) shown in Figure 2c reveal that P(THBQ-Al) is amorphous, whereas THBQ is highly crystalline. In addition, P(THBQ-Al) exhibited improved thermal stability compared to THBQ. As shown in the thermogravimetric analysis (TGA) profiles of THBQ and P(THBQ-Al) in N2 atmosphere, P(THBQ-Al) showed a weight loss at approximately 350 oC, whereas THBQ was decomposed at approximately 250 oC (Figure 2d). The superior thermal stability of P(THBQ-Al) to THBQ is attributable to its stronger Al-O bonding than H-O bonding in THBQ. Figure 2e and 2f show field emission scanning electron microscopy (FE-SEM) images of THBQ and P(THBQ-Al), respectively. While the size of THBQ plates was tens of micrometers, that of agglomerated P(THBQ-Al) powders ranged from hundreds of nanometers to a few micrometers.77


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Figure 1. (a) Synthetic scheme and (b) electrochemical reaction mechanism of P(THBQ-Al).


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Figure 2. (a) FT-IR spectra of P(THBQ-Al) and THBQ. (b) Al 2p XPS spectrum of P(THBQAl). (c) XRD patterns and (d) TGA analysis of P(THBQ-Al) and THBQ. SEM images of (e) THBQ and (f) P(THBQ-Al). (g) Optical images of TEGDME electrolytes after storing each THBQ and P(THBQ-Al) powder for one week (1 mg mL−1).


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The electrochemical performances of THBQ and P(THBQ-Al) electrodes were evaluated in the voltage range from 1.5 to 3 V (vs. Na/Na+) at a specific current of 20 mA g−1 (0.2 C) using a half cell comprising a sodium metal electrode and 1 M NaClO4 in tetraethylene glycol dimethyl ether (TEGDME). Figure 3a and 3b show the voltage profiles of P(THBQ-Al) and THBQ electrodes, respectively. P(THBQ-Al) delivered a high reversible capacity of approximately 113 mA h g−1, whereas THBQ delivered a negligible capacity. The theoretical specific capacity of P(THBQ-Al) is 288 mA h g−1, assuming that six carbonyl groups in the repeating group of P(THBQ-Al) can store 6 Na+ cations through the reaction mechanism shown in Figure 1b. Four plateaus were observed in the voltage profiles of P(THBQ-Al), which is consistent with four reversible redox peaks in the cyclic voltammogram of P(THBQ-Al) (Figure S1). In addition, P(THBQ-Al) exhibited excellent cycle performance, such as a negligible capacity fading over 100 cycles, as shown in Figure 3c. P(THBQ-Al) also showed stable cycle performance at the higher C-rate such as 100 mA g−1 (1 C) (Figure S2). The remarkable difference between P(THBQ-Al) and THBQ in electrochemical performance is attributed to the different solubilities of P(THBQ-Al) and THBQ in the electrolyte.59, 78 After storing THBQ powders in the electrolyte for a week, most THBQ powders disappeared and the color of the electrolyte changed from a transparent color to brown, as shown in Figure 2g. This indicates that THBQ is highly soluble in the electrolyte. In contrast to THBQ, no color change in the electrolyte was observed when P(THBQ-Al) powders were stored for a week. This indicates that P(THBQ-Al) is not soluble in the electrolyte. Moreover, the solubilities of the charged and discharged P(THBQ-Al) electrodes in the electrolyte were further examined through the color change of the electrolyte after storing each electrode for a week. In contrast to the pristine THBQ electrode, no color change in the electrolytes was observed after storing each pristine, charged, and discharged P(THBQ-Al) electrode (Figure 4a). This suggests


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Figure 3. Voltage profiles of (a) P(THBQ-Al) and (b) THBQ electrodes. (c) Cycle performance of THBQ and P(THBQ-Al). Numbers in (a) and (b) indicate the cycle number.


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Figure 4. (a) Optical images and (b) UV-Vis spectra of TEGDME electrolytes after storing bare THBQ, charged P(THBQ-Al), and discharged P(THBQ-Al) electrodes for one week.


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that the sodiated and desodiated forms of P(THBQ-Al) electrodes were also insoluble in the electrolyte. The dissolution behaviors of P(THBQ-Al) and THBQ electrodes were further supported by UV-Vis spectroscopy (Figure 4b). The absorption peak at 310 nm was observed in the UV-Vis spectrum of the supernatant electrolyte for the THBQ electrode, indicating the presence of benzoquinone derivatives dissolved in the electrolyte. However, no UV-Vis absorption peaks were observed for the charged and discharged P(THBQ-Al) electrodes, indicating that negligible amounts of P(THBQ-Al) were dissolved in the electrolyte. Thus, the THBQ electrode was dissolved in the electrolyte during cycling, leading to the loss of active materials. This loss resulted in poor electrochemical performance of THBQ. However, since the solubility of P(THBQ-Al) in the electrolyte is negligible, the loss of active materials in the P(THBQ-Al) electrode during cycling was suppressed. This is further supported by ex situ SEM analysis. The morphology of P(THBQ-Al) powders in the electrode remained unchanged after cycling because P(THBQ-Al) was not dissolved in the electrolyte during cycling, as shown in Figure S3. Therefore, the improved capacity retention of P(THBQ-Al) is attributed to the negligible solubility of P(THBQ-Al) in the electrolyte. To elucidate the electrochemical reaction mechanism of P(THBQ-Al), we performed ex situ XPS analysis. Figure 5b shows the O 1s XPS spectra of the P(THBQ-Al) electrodes collected at various points, as indicated in the corresponding voltage profile (Figure 5a). Each O 1s spectrum was deconvoluted into four peaks, such as a Na auger peak at 537.2 eV, C−O−Na bond at 534.1 eV, C=O bond at 532.6 eV, and Al−O bond at 531.5 eV.79 The peak intensity ratios of C=O and C−O were calculated by integrating the peak areas of C=O and C−O peaks, and their values were displayed in Figure 5c. The relative peak intensity of C=O gradually decreased during discharging (sodiation) and increased again during charging. This suggests that Na+ ions are


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Figure 5. (a) Voltage profiles of the P(THBQ-Al) electrode. (b) Ex situ O 1s XPS spectra of the P(THBQ-Al) electrodes and (c) the relative area ratios of C=O and C−O peaks shown in (b). (d) Ex situ C 1s XPS spectra of the P(THBQ-Al) electrodes. The numbers in (b), (c), and (d) represent the P(THBQ-Al) electrodes collected at various points indicated in (a).


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inserted into P(THBQ-Al) through the conversion of carbonyl groups (C=O) into sodium phenoxide groups (C−O−Na) during discharging, and vice versa during charging. The same reversible transformation of C=O into C−O−Na during sodiation and desodiation were further supported by the ex situ C 1s XPS spectra (Figure 5d). These results demonstrate that the electrochemical reaction of C=O groups in P(THBQ-Al) is highly reversible during sodiation and desodiation. Moreover, the peak position of Al−O bonding in the ex situ Al 2p XPS spectra was not shifted during sodiation and desodiation, as shown in Figure S4. This suggests that the Al−O coordination bonds in P(THBQ-Al) were not decomposed during sodiation and desodiation because Al3+ was not involved in the redox reaction. The reversible conversion of carbonyl groups (C=O) of P(THBQ-Al) into sodium phenoxide groups (C−O−Na) was also supported by ex situ IR analysis, as shown in Figure 6. The vibration peaks at 1105 and 1242 cm−1 originated from Al−O in the coordination complex and C−F in a PVdF binder, respectively, remained unchanged during sodiation and desodiation. The intensity of C−O peak at 1155 cm−1 and C−O−Na peak at 1530 cm−1 gradually increased and decreased during sodiation and desodiation, respectively. Inversely, the intensity of C=O peak at 1570 cm−1 gradually decreased and increased during sodiation and desodiation, respectively. This is consistent with ex situ XPS analysis.

CONCLUSIONS Amorphous P(THBQ-Al) coordination polymer was investigated for the first time as a cathode material for Na-ion batteries. P(THBQ-Al) was synthesized through a facile coordination-driven self-assembly of benzoquinonedihydroxydiolate (C6O6H22-) and Al3+. P(THBQ-Al) exhibited excellent electrochemical performance, including a high reversible capacity of 113 mA h g−1 and


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Figure 6. (a) Voltage profiles of the P(THBQ-Al) electrode. (b) Ex situ FT-IR spectra of the P(THBQ-Al) electrodes. The numbers in (b) represent the P(THBQ-Al) electrodes collected at various points indicated in (a).


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stable cycle performance, such as a negligible capacity fading over 100 cycles. Each benzoquinone unit in P(THBQ-Al) is capable of two electron reactions through the sodiation of its conjugated carbonyl groups, thus leading to a high reversible capacity. Moreover, electrochemically inert aluminum cation (Al3+) improved the structural stability of P(THBQ-Al) during cycling. While quinone-based single organic molecules, such as THBQ, were highly soluble in the electrolyte, the coordination polymer of P(THBQ-Al) was insoluble in the electrolyte, resulting in no loss of active materials during cycling. Therefore, the stable cycle performance of P(THBQ-Al) is attributable to its improved structural stability and negligible solubility in the electrolyte. We further clarified the reaction mechanism of P(THBQ-Al) through ex situ XPS and IR analyses. The reversible sodiation of C=O into C−O−Na was observed during cycling. Finally, we believe that coordination polymers are promising as electrode materials for Na-ion batteries because of their facile synthesis and sustainability.

ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publications web sites. Ex situ SEM images and Al 2p XPS spectra of the P(THBQ-Al) electrodes. Cyclic voltammogram and cycle performance of P(THBQ-Al) (PDF)

AUTHOR INFORMATION Corresponding Authors


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*E-mail: [email protected] (J.-C. Lee) *E-mail: [email protected] (K. T. Lee) Present Addresses † H. J. Kim is currently at the Department of Chemical Engineering and Materials Science, University of Minnesota, Twin Cities, 421 Washington Ave. SE, Minneapolis, MN, United States. § Y. Kim is currently at the Chemical Engineering, Materials Science and Engineering Program, Texas Materials Institute, The University of Texas at Austin, Austin, TX, 78712, United States. Author Contributions ‡These authors contributed equally. Notes The authors declare no competing financial interest.

ACKNOWLEDGMENT This research was supported by the National Research Foundation of Korea (NRF) Grant (No. NRF- 2016R1A2B3015956 and NRF-2016R1D1A1A02937104) and the Materials and Components Technology Development Program of MOTIE/KEIT, Republic of Korea [10050477, Development of separator with low thermal shrinkage and electrolyte with high ionic conductivity for Na-ion batteries].


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