Large Ï-Conjugated Porous Frameworks as Cathodes for Sodium-Ion

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Energy Conversion and Storage; Plasmonics and Optoelectronics

Large #-Conjugated Porous Frameworks as Cathodes for Sodium-Ion Batteries Hongyang Li, Mi Tang, Yanchao Wu, Yuan Chen, Shaolong Zhu, Bo Wang, Cheng Jiang, Erjing Wang, and Chengliang Wang J. Phys. Chem. Lett., Just Accepted Manuscript • DOI: 10.1021/acs.jpclett.8b01285 • Publication Date (Web): 30 May 2018 Downloaded from http://pubs.acs.org on May 30, 2018

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The Journal of Physical Chemistry Letters

Large

π-Conjugated

Porous

Frameworks

as

Cathodes for Sodium-Ion Batteries Hongyang Li,†,‡ Mi Tang,‡ Yanchao Wu,‡ Yuan Chen,‡ Shaolong Zhu,‡ Bo Wang,‡ Cheng Jiang,‡ Erjing Wang†,* and Chengliang Wang‡,* †

Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry-ofEducation Key Laboratory for the Green Preparation and Application of Functional Materials, Faculty of Materials Science and Engineering, Hubei University, Wuhan 430062, PR China. ‡ School of Optical and Electronic Information, Wuhan National Laboratory for Optoelectronics (WNLO), Huazhong University of Science and Technology, Wuhan, 430074, China.

AUTHOR INFORMATION Corresponding Author Email: [email protected]; [email protected]

ACS Paragon Plus Environment

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ABSTRACT: Organic sodium-ion batteries (OSIBs) are promising alternatives of inorganic lithium-ion batteries. The cathodes of OSIBs still suffer from the low capacity, poor rate performance and low cycleability. For the first time, we demonstrate the large π-conjugated porous frameworks (CPFs) as cathodes for organic sodium-ion batteries, motivated by the speculation that the πconjugated porous frameworks are capable of enhancing the charge transport, facilitating ionic diffusion, inhibiting the dissolution as well as improving the stability. The batteries based on the obtained CPFs indeed delivered a much better electrochemical performance than the small molecular construction units without any complex post-treatments. The moderate BET surface area of CPFs and the detailed analyses suggested that the micropores and the lamellar structure should be responsible to the fast ionic diffusion. We believe this work will provoke growing interests of CPFs for OSIBs with functional molecular design toward high performance and pave a venue to achieve OSIBs in large-scale applications.

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Lithium-ion batteries (LIBs) have become the most popular power supply for electric vehicles, consumer electronics and wearable electronic devices.1-2 However, the limited availability and non-renewability of lithium resources would confine the large-scale applications of LIBs.3-10 Therefore, alternative battery technology with high energy and power density and long cycle life by using abundant low-cost materials are desirable. Organic rechargeable sodium-ion batteries (OSIBs) are one of the most appealing alternatives of commercial inorganic lithium-ion batteries because OSIBs can combine the merits of sodium (similar chemical properties with lithium, comparable electrode potential only 0.3 V higher than lithium, resource abundance and possible use of low cost aluminum as current collector for both cathodes and anodes)3-8 and the advantages of organic electrodes (diversity, subjective design feasibility of molecular structure, structure flexibility for accommodating large Na-ions (radius: 1.02 Å (Na+) vs. 0.76 Å (Li+)), eco-friendly and availability from natural organic sources)11-18. Among the kinds of organic materials, carbonyls19-22 are promising materials as electrode materials due to the chemical stability of the charged/discharged states, the quantitative electrochemical reaction and the adjustable capacity and electrode potential, although the development of organic electroactive materials is still sluggish in low capacity, cycleability and rate performance. It is particularly of significance to enhance the charge and ionic transport and inhibit the dissolution of the electrode materials in the organic electrolytes for enhancing these electrochemical properties. π-Conjugated porous frameworks (CPFs), including covalent organic frameworks (COFs15, 2333

, a class of crystalline porous polymers), have been widely studied for gas storage, catalysis,

and optoelectronic applications. CPFs can also serve as promising alternatives for battery applications particularly if the frameworks contain large planar π-conjugated systems, because: 1) the large π-conjugated system is beneficial to the fast charge transport and stable


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charged/discharged states which will improve the rate performance and the cycleability;34-35 2) the large π-conjugated system may lead to face-to-face π-π intermolecular interactions and layerby-layer stacking, which will enhance the ionic transport and hence the rate performance;34, 36 3) the porous structure of the CPFs will also be conducive to the ionic diffusion, especially for large Na ions;24-27,

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4) the polymeric nature of CPFs will inhibit the potential dissolution of the

electrode materials and thereby improve the cycleability. However, there are still few reports on CPFs as electrode materials for rechargeable sodium-ion batteries.

HN O O O NH2 O

O HO

CHO OH

O NH O

+ OHC O

O

NH2

CHO O O

DAPT

O

N H

OH O

O O

O HN

TFP O NH O

H N

O DAPT-TFP-CPF

Scheme 1. Schematic diagram and synthesis route of DAPT-TFP-CPF. Here, pentacenetetrone (PT), a large π-conjugated system is used as the main construction unit to compose the frameworks (DAPT-TFP-CPF, Scheme 1) for sodium-ion batteries, as a proofof-concept. The monomer PT has been adopted in sodium-ion batteries as cathodes in our previous work37, which can accommodate 4 Na ions38-39 and deliver a theoretical capacity of 317 mAh g-1. However, it only gave a reversible capacity of ~73 mAh g-1, due to its dissolution in the electrolyte, even though a selectively permeable membrane has utilized to alleviate the dissolution and enhance the cycleability. The utilization of membrane also blocked the ionic transport and hence resulted in much lower capacity at high rate (e.g. lower than 50 mAh g-1 at a


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current density of 1000 mA g-1). In this paper, PT-based CPFs is designed and show a high reversible capacity of 150 mAh g-1 at a current density of 100 mA g-1 without any further posttreatments. At a high current density of 1000 mA g-1, the CPFs still displays a reversible capacity of 120 mAh g-1 even after 1400 cycles. These results suggested the efficiency of CPFs with large π-conjugated systems for fast-charge and -discharge OSIBs with high capacity and cycleability. To the best of our knowledge, this probably is the first work on OSIBs by using CPFs as cathodes. In order to form a π-conjugated porous frameworks, a typical linker40-41 1,3,5triformylphloroglucinol (TFP) was used to connect PT (linkage40) through reaction with amino groups. The reactants TFP42 and 1,8-diaminopentacene-5,7,12,14-teraone (DAPT)43 were obtained according to previous reports, respectively. The DAPT-TFP-CPF was synthesized from TFP and DAPT through a modified procedure27 and the synthetic route is showed in Scheme 1 (more experimental details see supporting information notes and Figure S1-S3). The chemical composition and structure of DAPT-TFP-CPF was confirmed by the Fourier transform infrared reflection (FTIR), solid-state

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C nuclear magnetic resonance spectroscopy (13C NMR) and

elemental analysis (EA, Table S1). The strong absorption peaks at 1668, 1669 and 1643 cm–1 in FTIR spectra are assigned to the stretching vibrations of carbonyl groups (C=O) in TFP, DAPT and DAPT-TFP-CPF, respectively (Figure 1a). All the three materials showed strong absorption around 1600 cm-1, which can be identified to the stretching vibrations of C=C groups. The reactant DAPT showed clear -NH2 stretching band at 3438 cm-1, which disappeared in the product of DAPT-TFP-CPF. Simultaneously, there are two peaks around 1200 cm-1 in the spectra of DAPT-TFP-CPF, which can be assigned to C-N and C-O groups and are also present in the reactant, DAPT and TFP, respectively. These results proved the successful preparation of


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proposed CPFs. Moreover, the absorption around 1400 cm-1 enhanced significantly, which belonged to fused rings and confirmed that the π-conjugated system was further extended due to the formation of CPFs. These results also support the irreversible tautomerism from enol to keto as reported previously44-45. To further probe the detailed structure of DAPT-TFP-CPF, the solidstate 13C NMR spectroscopy was performed. The 13C NMR spectra of DAPT-TFP-CPF showed a clear signal at 181.206 ppm (Figure 1b), corresponding to the carbon atoms in carbonyl groups. The peak at 134.379 ppm affirmed the existence of the -C-N bonds, which forcefully proved the formation of DAPT-TFP-CPF. The strong peaks at 124.367 and 108.275 are assigned to the carbons on the benzene (or conjugated rings) and olefinic bonds (C=C), respectively. All of these results demonstrated the chemical composition and structure of the products, which agreed well with the proposed CPFs. The morphology and inner stacking motif was further characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM) and powder X-ray diffraction (XRD). The SEM images (Figure S4) and TEM images (Figure 1d) showed clear two dimensional (2D) lamella structure of DAPT-TFP-CPF. The XRD patterns exhibited three peaks at 11.05°, 26.14° and 42.7°, which correspond to a d-spacing of 8.0, 3.4 and 2.1 Å, respectively (Figure 1c). The interfacial distance of 3.4 Å is close to the π–π intermolecular interactions, which is consistent with the previous reports of similar COFs27,

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and typical π–conjugated

systems36, 46. The periodic lattice in the 2D plane is about 4.0 nm, which is about five times of dspacing of 8.0 Å. The Brunauer–Emmett–Teller (BET) surface area of DAPT-TFP-CPF calculated from its N2 sorption isotherm at 77 K is 68.02 m2 g-1. This BET surface area is much lower than those of reported COFs15, 29. The powder showed two kinds of pores with micropore diameter of 8.1 Å and mesopore diameter of 40 nm, respectively (Figure S5). This porous


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structure would be conducive to the ionic transport for sodium-ion batteries. The absence of diffraction peaks around 2~3° (d-spacing of 4.0 nm, corresponding to the periodic lattice in the 2D plane if forming COFs) and mesopores with diameter of 4.0 nm indicated that the obtained polymers are porous frameworks rather than crystalline COFs. Nevertheless, the obtained CPFs showed quite similar properties with those of previously reported COFs (see following). The thermogravimetric analysis (TGA) showed that the obtained CPFs had high thermal stability without obvious decomposition under 450 °C (Figure S6).

Figure 1. a) FTIR spectra of DAPT-TFP-CPF. The spectra of TFP and DAPT are also shown for comparison. b)

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C NMR spectra, c) XRD patterns and d) TEM images of DAPT-TFP-CPF

powder, showing lamellar structure.


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The electrochemical performance of DAPT-TFP-CPF as potential cathode materials for sodium-ion batteries was studied by using a series of half-cells with sodium metal as the counter electrode. The electrode films were fabricated by mixing DAPT-TFP-CPF with super P (conductive additive) and PVDF (binder) in a weight ratio of 5:4:1. Figure 2a displays the typical cyclic voltammograms (CV) of the DAPT-TFP-CPF electrodes in the range from 3.2 to 0.8 V at a scan rate of 0.1 mV s-1. From the CV curves, the CPFs showed three reduction peaks around 1.2, 1.9 and 2.3 V (vs. Na/Na+) during the cathodic scan, corresponding to storage of charges and the insertion of Na+. The anodic scan gave three oxidization peaks around 1.3, 2.0 and 2.34 V (vs. Na/Na+), which indicated the loss of electrons and the extraction of Na+. The reduction peaks lower than 1.0 V can be ascribed to the irreversible formation of solid-electrolyte interface (SEI),34 which disappeared in the subsequent cycles. The formation of SEI is probably originated from the conductive additives (see following). The three redox peaks in the following CV curves showed similar shapes, equal reduction/oxidization currents and insignificant overpotential (differences between reduction and oxidization pairs are smaller than 0.1 V). These results showed the reversibility of DAPT-TFP-CPF electrodes. The low overpotential also implied the low resistances for charge transport and ionic diffusion. The CV curves after 5 cycles kept similarly, indicating the stability of DAPT-TFP-CPF electrodes during cycling. As control experiments, the electrochemical performances of super P, DAPT and TFP were also studied (Figure S7, S8 and S9). It is clear that DAPT showed similar redox peaks with those of DAPTTFP-CPF in shapes and electrode potentials. On the other hand, super P and the reactant TFP only displayed peaks lower than 1.0 V, which decreased rapidly during cycling. These results suggest that the electrochemical active centers in DAPT-TFP-CPF are located at the DAPT skeletons. In addition, the currents decreased gradually in the subsequent cycles of DAPT


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electrodes, which can be ascribed to the dissolution of DAPT in the electrolytes.37 The currents of DAPT-TFP-CPF electrodes kept stable, indicating its insolubility due to the formation of CPFs. Figure 2b shows the charge-discharge profiles of DAPT-TFP-CPF electrodes between 3.2 and 0.8V at a rate of 100 mA g-1 (1C= 177 mA g-1). There are three clear charge/discharge plateaus located at ca. 1.2, 1.9, and 2.3 in the charge-discharge profiles, which coincide well with the redox peaks in the CV curves (Figure 2a). The overpotentials for every redox pair are inappreciable, showing the reversibility of DAPT-TFP-CPF. The initial discharge and charge capacities were 248.4 and 179.6 mAh g-1, respectively (Figure 2b and 2c). The irreversible capacity loss observed in the first cycle can be ascribed to the SEI phenomenon34, which can be observed from the irreversible reduction peaks lower than 1.0 V in the CV curves (Figure 2a) and the capacity contribution from this region (Figure 2b). The discharge capacity became stable after 10 cycles to a reversible capacity of 168 mAh g-1 with Coulombic efficiency reaching to 100% (Figure 2c). This capacity is quite close to the theoretical specific capacity (177 mAh g-1), in terms of that the capacity contribution is only originated from the carbonyl groups on DAPT skeletons. The electrodes exhibited a high capacity even after 1000 cycles (145 mAh g-1) at a current density of 100 mA g-1, suggesting its good cycling stability. As control experiments, the capacity contribution from super P is negligible and lower than 8 mAh g-1 (Figure S7). The reactant TFP is also almost inactive in this region (Figure S9). Although DAPT showed similar redox peaks and charge/discharge plateaus located at similar electrode potentials, the capacity was much lower than that of DAPT-TFP-CPF and decreased rapidly to lower than 40 mAh g-1. DAPT has a much higher theoretical specific capacity (291 mAh g-1) than that of DAPT-TFPCPF; hence, the low experimental capacity of DAPT and its decreasing during cycling probably


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can be ascribed to the dissolution of this small molecule. All of these results showed the good electrochemical performance of DAPT-TFP-CPF with high reversible capacity and high stability.

Figure 2. Electrochemical performance of DAPT-TFP-CPF electrodes. a) CV curves of DAPTTFP-CPF based batteries in the first 10 cycles. b) and c) Electrochemical performance of DAPTTFP-CPF at a current density of 100 mA g-1: b) voltage profiles (1st, 5th, 50th, 100th, and 200th cycles are selected as representatives) and c) cyclability. d) Long-term cyclability of DAPT-TFP-


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CPF at a current density of 1000 mA g-1. e) Rate cyclability and f) corresponding voltage profiles of DAPT-TFP-CPF based batteries (from right to left: 50, 500, 1000, 2000, 5000, 50 mA g-1). We also performed the long-term cycling of DAPT-TFP-CPF electrode at a 1 A g−1 (~5.6C) rate (Figure 2d). The cell delivered an initial capacity of 257.5 mAh g-1, which decreased to 127.7 mAh g-1 in the first 10 cycles with Coulombic efficiency slowly approaching to 100%. The capacity became stable afterwards and the cell provided a stable capacity of 121 mAh g-1 even after 1400 cycles, indicating the excellent stability of the DAPT-TFP-CPF during cycling. The high cycleability of DAPT-TFP-CPF proved that the polymeric CPFs can lower the solubility of active materials in electrolytes and thus is able to enhance the cycling stability. Moreover, the extended π–conjugated system as construction unit is helpful for enhancing the charge transport. The resulted layer-by-layer (π–π stacking) and the porous structure of CPFs can facilitate the ionic transport. All of these will contribute to the high performance at high rate. Figure 2e depicts the rate cycleability of DAPT-TFP-CPF electrodes. DAPT-TFP-CPF cycled at a current density of 1000, 2000 (~11C) and 5000 (~28C) mA g-1 displayed capacities still higher than 100 mAh g-1, with capacity retention of 92%, 85% and 72%, respectively, compared to the capacity at 100 mA g-1. In this case, only minutes are required for a full charge. From Figure 2f, it is clear that the plateaus in the discharge/charge profiles of DAPT-TFP-CPF only change slightly ( 0.9), indicating that the capacitive process played a leading role in these electrodes. The capacitive effect of DAPT-TFP-CPF electrodes is meaningful because the moderate BET surface area of DAPTTFP-CPF suggested that the micropores and the lamellar structure should be responsible to the fast ionic diffusion. The capacitive effect probably can be attributed to the good charge transport character (due to the π-π interactions) and the high ionic diffusion ability (because of the porous CPFs). All of these account for the high electrochemical performance of DAPT-TFP-CPF electrodes.


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Figure 3. a-b) XPS spectra of DAPT-TFP-CPF electrodes (pristine, discharged to 0.8 V and recharged to 3.2 V respectively). a) C1s spectra and b) O1s spectra. The peak at around 291~292 eV in C1s spectra should be assigned to C-F bond in PVDF binder. The peak at about 537 eV in O1s spectra probably can be recognized as the sodium Auger peak, which was not observed in the pristine samples. c) CV curves of DAPT-TFP-CPF electrodes at different scan rates. d) The log relationship of the peak currents (in Figure c) and the scan rates. In summary, we demonstrated the first π-conjugated porous frameworks as cathodes for organic sodium-ion batteries. The batteries based on DAPT-TFP-CPF delivered a reversible capacity of 145 mAh g-1 over 1000 cycles at 100 mA g-1 and a reversible capacity of 120 mAh g1

over 1400 cycles at a high current density of 1000 mA g-1. These performance are much higher


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than the small molecular construction units (PT, 73 and 50 mAh g-1 at current density of 100 and 1000 mA g-1, respectively, even after complex post-treatment). The improved performance can be ascribed to the extended π-conjugated systems of the whole π-conjugated porous frameworks s. The extended π-conjugated systems stabilize the materials and improve the charge transport. The unique conjugated-porous-frameworks structure is beneficial for ion diffusion, leading to capacitive effect rather than dominant ionic diffusion. The moderate BET surface area of CPFs and the detailed analyses suggested that the micropores and the lamellar structure should be responsible to the fast ionic diffusion. Moreover, the polymeric frameworks effectively inhibit the dissolution of active molecule and hence boost the long-term cycleability of electrodes. We believe this work will motivate growing interests of π-conjugated porous frameworks for OSIBs with functional molecular design toward high performance and pave a venue to achieve OSIBs in large-scale applications.

ASSOCIATED CONTENT Supporting Information. Experimental details, electrochemical performance of super P, TFP and DAPT, BET data, TGA, SEM images, XPS and EIS data of DAPT-TFP-CPF. The Supporting Information is available free of charge on the ACS Publications website at DOI: AUTHOR INFORMATION Corresponding Authors * [email protected]


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* [email protected] Notes The authors declare no competing financial interest. ACKNOWLEDGMENT This work was supported by the National 1000-Talents Program, the National Natural Science Foundation of China (51773071, 51603063), Wuhan Science and Technology Bureau (2017010201010141) and the Fundamental Research Funds for the Central Universities (HUST: 2017KFYXJJ023, HUST: 2017KFXKJC002). We are grateful to Prof. Dr. Daqiang Yuan (Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences) for his valuable comments. The authors thank Huazhong University of Science and Technology Analytical & Testing Center for XRD and TEM measurements.


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