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Three-Dimensional Arylene Diimide Frameworks for Highly Stable Lithium-Ion Batteries Tyler B Schon, Andrew J Tilley, Emily L Kynaston, and Dwight S. Seferos ACS Appl. Mater. Interfaces, Just Accepted Manuscript • Publication Date (Web): 21 Apr 2017 Downloaded from http://pubs.acs.org on April 23, 2017

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ACS Applied Materials & Interfaces

Three-Dimensional Arylene Diimide Frameworks for Highly Stable Lithium-Ion Batteries Tyler B. Schon, Andrew J. Tilley, Emily L. Kynaston, Dwight S. Seferos* Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. Email: [email protected] KEYWORDS: lithium-ion batteries, organic frameworks, organic electrodes, triptycene, arylene diimides

ABSTRACT: Lithium-ion batteries are the best commercial technology to satisfy the energy storage needs of current and emerging applications. However, the use of transition metal-based cathodes precludes them from being low cost, sustainable, and environmentally benign, even with recycling programs in place. In this study, we report a highly stable organic material that can be used in place of the transition metal cathodes. By creating a three-dimensional framework based on triptycene and perylene diimide (PDI), a cathode can be constructed that mitigates stability issues that organic electrodes typically suffer from. When a lithium-ion battery is assembled using the PDI-triptycene framework (PDI-Tc) cathode, a capacity of 75.9 mAh g-1 (78.7 % of the theoretical value) is obtained. Importantly, the battery retains a near perfect coulombic efficiency, and >80% of its capacity after cycling 500 times, which is the best value reported to date for PDI-based materials.

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Introduction Inexpensive, environmentally friendly, and high performance energy storage is important due to the widespread use of portable electronics, the advent of electric vehicles, and the implementation of grid-scale energy storage for renewable power generation.1,2 In the current state of electrochemical energy storage, lithium-ion batteries are viewed as the best technology to satisfy the energy requirements of these applications due to their high energy density compared to other battery technologies.3 However, the redox-active cathode materials in commercial lithium-ion batteries are made from heavy transition metals, cobalt being the most widely used.1 This is a significant concern for their cost, sustainability, and the environment during both the manufacturing and disposal streams of lithium-ion batteries. Additionally, the raw materials for cobalt-based cathodes are sourced primarily from politically unstable regions of the world, creating potential supply-chain issues that could further inflate the production cost of these key battery components. Organic electrodes are a promising alternative to metal-based inorganic electrodes, where the inorganic redox-active component is replaced by a carbon-rich material.4,5 Organic electrodes can address many of the issues that their inorganic counterparts face due to the high natural abundance of organic materials, their relatively low toxicity, and ease of disposal. Organic electrodes have been shown to yield high performance in different energy storage devices including lithium-ion batteries,6-9 redox-flow batteries,10-13 and supercapacitors.14-16 However, their limited cycling stability severely impedes the further development and ultimate commercialization of these innovative materials. The instability of organics is typically attributed to dissolution of the redox active materials,17-19 chemical reactions that degrade the electrode


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material,20 and conformational changes in the molecular structure upon charging and discharging.21 One of the most promising classes of organic materials for energy storage are arylene diimides such as perylene diimide (PDI) or naphthalene diimide (NDI). These compounds are widely used in the pigment industry and have been extensively applied in a wide range of electronic applications including thin-film transistors, organic solar cells, and sensors.22 PDIs and NDIs reversibly accept up to two electrons at room temperature (at ~2.5 V vs Li/Li+), making them popular candidates for energy storage. However, one of the main disadvantages of PDIs and NDIs is their severe capacity fading due to dissolution of the redox-active materials.23-25 Prevalent strategies for improving the cycling stability of these compounds include designing rigid molecular geometries that decrease solubility,25 creating nanostructures of the organic materials,9,26,27 incorporating PDI and NDI units into polymeric structures,28-33 and creating insoluble two-dimensional covalent organic frameworks (COFs).34-37 In particular, electrodes based on frameworks are attractive due to their permanent porosity which can lead to rapid ion diffusion, and high power density.38-42 However, these approaches still have various drawbacks and yield less than optimal device stability. Alternate strategies that further increase cycling stability while taking advantage of full redox capability are desirable. Here, we report the first examples of lithium-ion batteries that use 3D COFs as the cathode material. Using a trans-functionalized triptycene as one building block and PDI/NDI as the linker, we construct novel redox-active 3D COFs. With the PDI based system, a lithium-ion battery with a capacity of 75.9 mAh g-1 and a voltage of 2.5 V vs Li/Li+ is obtained. The battery retains a near perfect coulombic efficiency, and has excellent stability retaining 88.2% of its capacity after 200 cycles. Moreover, it only loses an additional 8% of capacity in 300 cycles


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from cycle 200 to cycle 500. To the best of our knowledge, no PDI-containing material has ever been shown to be stable for this large amount of cycling for lithium-ion batteries.29,35,30,36,43-45 This work thus describes a new class of highly stable cathode materials for battery applications.

Experimental Procedures: Synthesis of 1: The synthesis of 1 was carried out using a previously reported procedure.46 General synthesis of arylene diimide triptycene frameworks: 1 equivalent of 1, 1.5 equivalents of the dianhydride monomer, 0.8 equivalents of zinc (II) acetate, and 260 equivalents of imidazole were mixed together to homogenize and then added to a flame-dried 3-necked flask fit with a reflux condenser. The mixture was backfilled with argon three times to remove any oxygen. The reaction mixture was stirred at 160oC for 24 hours. Upon completion, the reaction was cooled to room temperature and methanol was added to dissolve the solid imidazole. The reaction was then poured into methanol and filtered through a Soxhlet thimble. The crude material was purified by Soxhlet extraction with methanol for one day and then chloroform for 5 hours to remove imidazole, impurities, and any low molecular weight species. Characterization of PDI-Tc: Performed on a 3.34 mmol scale. Quantitative yield (2.87 g). 13C CP/MAS NMR δ: 163.38, 146.55 ,133.08, 124.06, 53.86 ppm. Elemental analysis calculated for C56H24N3O6: C, 80.57; H, 2.90; N, 5.03. Found: C, 70.02; H, 3.24; N, 4.36. Characterization of NDI-Tc: Performed on a 0.835 mmol scale. Quantitative yield (603 mg). 13

C CP/MAS NMR δ: Elemental analysis calculated for C41H17N3O6: C, 76.04; H, 2.65; N, 6.49.

Found: C, 67.63; H, 2.86; N, 7.09. Purification of frameworks by precipitation: To further purify the frameworks and decrease the particle size, 144 mg of the frameworks were dissolved in 15 mL of methanesulfonic acid


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overnight with stirring. The solution was then added dropwise to 2.5 L of methanol in a rapidly stirring beaker. The suspension was then concentrated on a rotary evaporator until the volume of methanol was approximately 500 mL. The suspended frameworks were collected by centrifugation, washed with methanol three times, and dried at 200oC under vacuum overnight. Preparation of coin cell lithium-ion batteries: The cathode containing the frameworks was prepared by mixing the purified framework, carbon Super P, and PVDF in a 60:30:10 (w/w/w) ratio and suspending the mixture in NMP at a concentration of 150 mg mL-1. The slurry was sonicated for 1 hour, stirring every 15 minutes to homogenize. The slurry was cast onto an aluminum foil current collector and dried according to a previously published procedure.21 The films were approximately 75µm thick (Figure S12) with approximately 3.0 mg/cm2 (1.8 mg/cm2, or 240 mg/cm3, of the frameworks). CR2023-type coin cells were purchased from MTI Corporation. A copper foil with a diameter of 16 mm (McMaster-Carr) was used as the anodic current collector, a lithium foil with a diameter of 16 mm was used as the anode, and a Celgard polypropylene separator with a diameter of 19 mm was used to prevent short circuiting. An electrode punch (DPM Solution Inc.) was used to cut the electrodes to a 16 mm diameter and a hydraulic press (BT Innovations) was used to hermetically seal the cells. Approximately 80 µL of electrolyte (1:1 (v/v) ethylene carbonate:dimethoxyethane, 1 M LiPF6) was used to fill the cells prior to sealing.

Results and Discussion We have recently reported the use of a three-dimensional (3D) thiophene-based COF in an organic supercapacitor.47 This material has an excellent stability, retaining 80% of its initial current when cycled 500 times. Although this work demonstrated that 3D COFs are stable as


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supercapacitors, this methodology has not been applied to batteries. Incorporating a redox-active 3D COF into a lithium-ion battery could yield the much-needed improvement in stability while maintaining high capacity. Three-dimensional PDI-triptycene (PDI-Tc) and NDI-triptycene (NDI-Tc) frameworks were synthesized in quantitative yields by the condensation of perylene-3,4,9,10-tetracarboxylic acid dianhydride or naphthalene-1,4,5,8-tetracarboxylic acid dianhydride, respectively, with amine-functionalized triptycene 1 (Scheme 1). Using a trans-functionalized triptycene as the vertex units is shown to yield three-dimensional frameworks (Figure 1).48

49,50

Characterization

of the resultant materials with Fourier-transform infrared spectroscopy (FTIR) provides evidence of the formation of the diimide functionalities. For PDI-Tc, symmetric and asymmetric imide carbonyl stretches appear at 1771 and 1756 cm-1, respectively, carbon-nitrogen bond stretches appear at 1346 cm-1, and an imide ring deformation stretch appears at 732 cm-1 (Figure 2a). For NDI-Tc, symmetric and asymmetric imide carbonyl stretches appear at 1785 and 1714 cm-1, respectively, carbon-nitrogen bond stretches appear at 1337 cm-1, and an imide ring deformation stretch appears at 764 cm-1.

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C cross-polarization magic-angle-spinning (CP-MAS) NMR

provides further evidence for the formation of the frameworks. The successful formation of the PDI-Tc framework is confirmed by the presence of a carbonyl carbon peak at 163.3 ppm, various peaks corresponding the aromatic carbons from 146.6 to 124.1 ppm, and the aliphatic carbons in the triptycene linker at 53.9 ppm (Figure 2b). Similar peaks are observed for the NDI-Tc framework (Figure S1) and they are consistent with what has been reported in the literature.31,51,48 High resolution X-ray photoelectron spectroscopy (XPS) shows the successful formation of the appropriate elemental functionalities in the frameworks. The C1s region of PDI-Tc can be


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deconvoluted into 5 peaks corresponding to the sp3 carbon at 284.08 eV, the aromatic sp2 carbons at 284.96 eV, the sp2 carbons bonded to the diimide nitrogens at 286.17 eV, the carbonyl carbon at 288.18 eV, and a broad shake-up feature at 290.17 eV (Figure 2c). Similar peaks are found for NDI-Tc in the C1s spectrum at 283.99 eV, 285.09 eV, 285.95 eV, 288.75 eV, and 290.47 eV for the sp3 carbons, the aromatic sp2 carbons, the sp2 carbons bonded to the diimide nitrogens, the carbonyl carbons, and the shake-up feature respectively (Figure S1). The high resolution N1s XPS spectra of both frameworks show a single symmetric peak located at 400.28 eV and 400.68 eV for the PDI-Tc and NDI-Tc framework respectively (Figure S1, and Figure S2). Elemental analysis confirms that the frameworks contain carbon, hydrogen, and nitrogen in amounts that are similar to the theoretical values (Experimental Section). Deviations from the theoretical values are due to defects within the frameworks, that are expectedly higher than those found in two-dimensional systems, and residual solvent trapped inside the frameworks.47,52 The powder X-ray diffraction (PXRD) pattern of PDI-Tc shows sharp diffraction peaks, confirming the crystalline nature of the framework. The peaks correspond to diffractions at 9.32 Å, 7.15 Å, 3.58 Å, 3.23 Å, and 3.19 Å (Figure 2d). However, the PXRD spectrum of NDI-Tc has only a broad amorphous halo corresponding to a spacing of 3.03 Å indicating that this framework lacks crystallinity (Figure S1). CO2 adsorption measurements of PDI-Tc and NDI-Tc show a typical type I isotherm with very little hysteresis, which indicates that these materials are microporous (Figure 2e and Figure S3). From the gas adsorption data, the frameworks are found to have surface areas of 236.9 and 335.9 m2 g-1 for PDI-Tc and NDI-Tc respectively. The pore size distribution, calculated from the adsorption isotherms by density functional theory, reveals that the pore sizes are approximately 3.5 Å, 4.6 Å, and 8.2 Å for the PDI-Tc sample which is


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roughly in agreement with the PXRD data (Figure 2f). The NDI-Tc has similar pore sizes of 3.5 Å, 4.8 Å, and 8.2 Å (Figure S3). The PDI-Tc framework can be cast into an electrode with a conductive carbon additive (Super P) and a polymeric binder that has an ideal morphology for battery applications. In the electrode, the PDI-Tc framework provides faradaic redox activity that is used to store charge in the battery electrode, the conductive carbon provides an electrical conduction path throughout the electrode, and the binder prevents delamination from the current collector and acts as a ‘glue’ to hold the electrode together. To ensure the best performance in a lithium-ion battery, the materials were first dissolved in methanesulfonic acid and precipitated into methanol to decrease the particle size and remove any zinc impurities that could impact the electrochemical performance. Complete removal of the zinc impurities was confirmed by XPS (Figure S4). The precipitated frameworks were then mixed with Super P and polyvinylidene fluoride (PVDF) at a ratio of 60:30:10 (w/w/w), mixed in N-methyl pyrrolidone (NMP), and cast onto an aluminium foil current collector. By TEM, the PDI-Tc frameworks appear as irregular aggregates that are approximately 200 nm in diameter (Figure S6). When examining the PDI-Tc electrode by SEM, rod-like aggregates of PDI-Tc, approximately 1 to 7 µm in length and 500 nm wide, are observed that are dispersed evenly in the Super P matrix (Figure 3a,b). This morphology is ideal because it provides an electronic conduction path to the PDI-Tc active material, via the carbon Super P, and a relatively short diffusion length for lithium ions within the PDI-Tc aggregate. The precipitated NDI-Tc frameworks have plate-like and irregular aggregate shapes that range in size from approximately 200 nm to 500 nm in width after precipitating in methanol (Figure S6). When cast into an electrode, these aggregates amalgamate to form large, non-conductive structures, as indicated by the high degree of charging in the SEM images (Figure 3c,d).


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The battery performance of the PDI-Tc framework exceeds that of any previous PDI-based frameworks and polymers (Table S2). Performance was tested by assembling coin cells using the framework electrodes as cathodes and lithium metal as the anode. The PDI-Tc framework has one reversible redox wave, observed by cyclic voltammetry, centred at 2.5 V vs Li/Li+ (Figure 4a). The redox wave is due to the reversible reductions of two carbonyl groups of the PDI units (Scheme 2).31,45 The capacity of the lithium-ion battery was tested with galvanostatic charge/ discharge measurements (Figure 4b, Table S3). When cycled at 0.05 C (nC is the current it would take to charge/ discharge the cell fully in 1/n hours), the capacity is 75.9 mAh g-1 corresponding to 78.7 % of the theoretical capacity (96.4 mAh g-1). When the current is increased by 2 orders of magnitude, the capacity is 22.4 mAh g-1, 29.5% of that obtained at 0.05 C. Importantly, after cycling the cell 500 times at 2 C it retains 80.2% of its original capacity, showcasing the framework’s excellent cycling stability (Figure 4c). The stability of the PDI-Tc framework much better than the PDI small molecule, which rapidly decays to 13.6 % of the original capacity after 100 cycles, and 7.48 % of the original capacity after 500 cycles (Figure S7). The excellent stability of the PDI-Tc framework is the result of the highly insoluble nature of the three-dimensional frameworks as well as the highly reversible electrochemistry of the PDI units (Figure 4c, inset). The coulombic efficiency over the entire cycling stability test for the PDI-Tc battery is ~100% demonstrating that no irreversible processes take place during charging and discharging. Additionally, the framework is also very stable at low charging and discharging rates, where material dissolution is more problematic, retaining 82% of its capacity after 200 cycles at 0.5 C (Figure S8). The charge transfer and equivalent series resistance, measured by electrochemical impedance spectroscopy, remain almost constant throughout the cycling experiment (Figure S8 and Table S1). The utility of the PDI-Tc framework battery was


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demonstrated by using it to light up a red LED (Figure 4d). The NDI-Tc framework did not display optimal performance, likely due to the large aggregate size and low crystallinity of the frameworks in the electrode (Table S3, and Supporting Information for discussion).

Conclusions In summary, we have demonstrated the use of three-dimensional COFs as cathode materials for lithium-ion batteries for the first time. Using a PDI-based redox couple, a high reversibility and stability was achieved. The capacity reached 78.7% of the theoretical value with PDI-Tc at a rate of 0.05 C and retains 29.5% of this value when the current is increased by 2 orders of magnitude. The coulombic efficiency is ~100% throughout the experiment, demonstrating the almost perfect reversibility. Importantly, an excellent stability was demonstrated by cycling the battery 500 times at 2 C. The battery retained 80.2% of its capacity which is the best reported value for PDI-based polymers or frameworks. Our work demonstrates that three-dimensional COFs can form the basis of highly stable lithium-ion batteries. The NDI version of the same COF does not feature this high performance, which shows how critical molecular design is for organic battery applications. The replacement of the inorganic cathode materials with inexpensive, abundant organic materials such as the ones reported here should yield devices with a lower cost, greater sustainability, and a lower impact on the environment. We hope that this work will provide a new avenue towards the design of highly stable organic electrodes. By replacing the PDI units with ones that have a higher voltage and capacity, high-performance materials can be made without compromising stability.


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Figure 1. Simulated structure of the (a,c) PDI-Tc repeat unit and (b,d) the NDI-Tc repeat unit calculated using density functional theory (see Supporting Information). For the simulated structures, grey, red, blue and white spheres represent carbon, oxygen, nitrogen, and hydrogen atoms respectively.


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Figure 2. (a) FTIR spectra of the NDI-Tc and PDI-Tc frameworks in green and red respectively. (b)

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C CP-MAS NMR spectrum of PDI-Tc with the assigned carbon atoms. (c) Deconvoluted

C1s XPS spectrum of PDI-Tc with the corresponding assignments. (d) PXRD pattern of PDI-Tc with the labels corresponding to the spacing at the observed diffraction angle. (e) CO2 adsorption isotherm performed at room temperature for PDI-Tc. (f) Pore size distribution and pore volume curve calculated by density functional theory from the CO2 adsorption data in (e).


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Figure 3. (a, b) SEM image of the PDI-Tc electrode showing the PDI-Tc aggregates and the carbon Super P. (c, d) SEM image of the NDI-Tc electrode showing the large NDI-Tc aggregates and the carbon Super P. The distortion in the images in c and d is due to a charging effect on the non-conductive NDI-Tc aggregates. The PVDF homogenously coats the electrode components and therefore cannot be labelled.


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Figure 4. Electrochemical properties of the PDI-Tc lithium-ion battery. (a) Cyclic voltammogram of the PDI-Tc battery at a scan rate of 1 mV s-1. (b) Galvanostatic charge/discharge curves of the PDI-Tc battery at currents between 0.05 C to 5 C. (c) Capacity decay and coulombic efficiency of the PDI-Tc battery over 500 cycles at a current rate of 2 C. Inset: Photograph of PDI-Tc in a 1 M LiPF6 ethylene carbonate dimethyoxyethane (1:1 w/w) electrolyte. The light red colour near the bottom is due to a suspension of solid PDI-Tc near the sedimentation. (d) A photograph of a red LED powered using a PDI-Tc battery.


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Scheme 1. Synthesis of PDI-Tc and NDI-Tc frameworks

Scheme 2. (a) Redox mechanism for NDI units and (b) redox mechanism for PDI units. The third and fourth carbonyl groups on the arylene diimides do not undergo reversible reductions due to the distribution in conjugation required to reduce them.

ASSOCIATED CONTENT The Supporting Information is available free of charge. Additional characterization of the PDI-Tc and NDI-Tc frameworks, electrochemical testing of the NDI-Tc framework, and computational modelling details of the frameworks (PDF)

AUTHOR INFORMATION Corresponding Author


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*Email: [email protected] Notes The authors declare no competing financial interest.

ACKNOWLEDGMENT This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) and the University of Toronto Connaught Foundation The authors would like to thank Prof. M. Taylor for the use of the FTIR spectrometer, Prof. K. Lian for use of the battery tester, and Prof. T. Bender for the use of the TGA. TBS and ELK acknowledge support from NSERC.

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