High Throughput Screening of Organic Electrode Materials for Lithium

Article pubs.acs.org/JPCC

High Throughput Screening of Organic Electrode Materials for Lithium Battery by Theoretical Method Shaorui Sun,*,† Yanhui Chen,†,‡ and Jun Yu§ †

Beijing Key Laboratory for Green Catalysis and Separation, College of Environmental and Energy Engineering, Beijing University of Technology, Beijing, 100124, China ‡ The Physics Department, Beijing Center for Physical and Chemical Analysis, Beijing, 100089, China § The Biological and Chemical College, Qinghai Nationalities University, Xining, Qinghai, 030031, China S Supporting Information *

ABSTRACT: Screening the appropriate organic electrode material of a lithium battery from the organic structure database by the theoretical method efficiently is crucial for the further experimental study. Unfortunately, the density functional theory is not appropriate due to that it fails to calculate the van der Waals interaction between the organic molecules. In this work, dispersion-corrected density functional theory (DFT-D2) was applied to study nine experimentally reported organic electrode materials, and the theoretical method successfully predicted their potentials, which suggests that it is a feasible method to search and investigate the organic electrode material. The method is further applied to investigate 31 organic crystallines selected from the CCDC (Cambridge Crystallographic Data Centre) database. The theoretical results show that the potentials range from 0.01 eV to 2.76 V, while the capacities distribute from 150 to 623 mAh·g−1, and most of the band gaps are smaller than 2.5 eV, which indicates that they are typical organic semiconductors with high electronic conductivity. The materials with a relatively high potential, high capacity, and small band gap are highligthed, including BAKGOJ, MEHROH, SUQDEN, and NUXGIW, which may be further investigated by experimenters.

I. INTRODUCTION Li−organic batteries, Li-ion batteries have already played a major role in power supply for electronic devices, tools, vehicles, and grid energy storages.1,2 The cathode material is one of the most important composites to improve the performance in Li-ion batteries researches and developments.3 Now, the commercial cathode materials, including LiCoO2,4 LiNiO 2,5 LiMn2 O4 ,6 and LiFePO 4,7 have been deeply investigated and widely applied. There are two shortcomings in such inorganic cathode materials: one is that the mineral resource is limited, especially for Co and Ni; the other is to produce or recycle inorganic compounds requiring high temperature as well as liberating large amounts of CO2, which is environmentally harmful.8 Recently, the organic-based electrode materials have attracted considerable attention due to their unique properties such as lightweight, flexible, abundant in nature, and low CO2 emission.9,10 Up to now, many organic cathode materials have been reported,11,12 among which the most important is the molecule containing the carbon−oxygen double bond (CO) in the carbonyl or carboxyl group. Until now, the charge/discharge mechanism of the organic cathode material remains incompletely understood. From the single molecule perspective, the double bond is broken into a single bond during the lithiated process, and the single bond returns into the double bond during the delithiated process. © 2015 American Chemical Society

With this model, some DFT (density functional theory) calculations were carried out, and the redox potential was calculated with the potential reference: the Li/Li+ potential is −3.0 V vs NHE (the normal hydrogen electrode reaction). As shown in Figure 1, the molecular system is always considered in

Figure 1. Structure of the delithiated and lithiated p-benzoquinone.

an electrolyte with a solvent model, PCM (polarized continuum model), and one side of the Li ion is bounded to the oxygen atom.13−17 In the real situation, after the Li ion inserts into the electrode materials, its chemical environment could not be simply considered as the electrolyte or vacuum. So far, the grain and crystalloid organic electrode materials have been widely reported, implying that they are the most important organic electrode materials. Millions of organic Received: September 3, 2015 Revised: October 21, 2015 Published: October 22, 2015 25770

DOI: 10.1021/acs.jpcc.5b08609 J. Phys. Chem. C 2015, 119, 25770−25777

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The Journal of Physical Chemistry C molecular crystals have been synthesized and collected in the CCDC (Cambridge Crystallographic Data Centre) database. Many of them are capable of storing lithium ions and could be the candidates for the electrode materials of Li-ion batteries. How to choose the appropriate compounds from the database with the theoretical method efficiently is the key to the further research. The DFT (density functional theory)18 calculation is very effective when working on the single molecule and the inorganic crystal, which both have strong bonds between the atoms (or ions). Organic molecular crystals have large distances between the molecules, and the van der Waals (VDW) interaction is the key force to bind the molecules with each other, which is beyond the limitation of DFT calculations.19,20 Recently, some methods are developed to calculate the VDW interaction between molecules with DFT.21,22 We have reported a theoretical work with the DFT-D223 method to study an ethoxycarbonyl-based organic electrode material, and the results, including the lattice parameters and redox potential, are in good agreement with the experimental results, which indicates that the method is a useful tool to study the organic electrode material.24 In the present work, the dispersioncorrected density functional theory (DFT-D),25,26 which is developed by Grimme, is applied to study the organic molecular electrode materials.27,28

V=−

Figure 2. Potentials of the nine reported organic materials.

for the experimental values, the blues are for the theoretical values of DFT with exchange-correlation potential parametrized by PBE, and the reds are for DFT-D2. Here, the experimental potential values are the average value over the full capacity range if the charge/discharge platforms are more than one. The average error between the experimental and theoretical values is about 10%, which suggests that the present calculation method is reliable evaluating the potential of organic electrode materials. In general, the theoretical potential is lower than the experimental value for each compound (except PACWUN).12 The difference may be due to the present dispersion-corrected method slightly overestimating the interaction between atoms in the lithiated state or underestimating that in the delithiated state. For the other 31 organic materials, which were not reported previously, their theoretical potentials are shown in Figure 3. The redox potentials of 13 materials are higher than 2.0 V, five are between 1.5 and 2.0 V, and 13 are lower than 1.5 V. The materials, with the potential higher than 1.5 V, could be applied as the cathode materials. None of the organic materials above has a potential higher than 3.0 V, and this may be due to the moderate redox reaction with the lithiated/delithiated process. In fact, the high potential may lead to safety problems in the organic system. By now, although we have not confirmed that any organic material’s potential cannot be higher than 3.0 V, the upper limit of the potential may be about 3.0 V based on the present calculation results. As shown in Figure 4, 17 of the materials’ theoretical capacities are higher than 274 mAh/g (the capacity of LiCoO2), and 35 higher than 170 mAh/g (the capacity of LiFePO4). Compared to the inorganic materials, many organic materials have a higher capacity. Tetrahydrofuran-3,4-dione (C4H4O3, HYFURN) is solid at room temperature, which has a fivemembered ring, and its capacity is 536 mAh/g. 2,3-Butanedione

III. RESULTS AND DISCUSSION In the present work, nine experimentally reported materials are investigated by the theoretical method, and the experimental and the theoretical potentials are all listed in Table 1. Beyond the above 9 materials, 31 organic crystal materials are stochastically selected, and their formulas and reference codes are listed in the Supporting Information. The theoretical redox potential (vs Li metal electrode) could be calculated by39 Table 1. Theoretical and Experimental Voltage of the Nine Organic Materials theoretical voltage (V) refcode

GGA-PBE

DFT-D2

experimental voltage (V)

1 2 3 4 5 6 7 8 9

PACWUN12 TCYQME31 QEGNEV32 ZOSYAH33 YOFROB34 MEJWED35 INDIGO36 DELXUO37 BZCBUO38

1.12 1.59 1.0 1.469 1.132 2.09 1.59 0.14 1.24

1.86 2.55 1.59 1.879 1.775 2.19 1.94 0.64 1.61

1.82 2.7 2.0 2.5 2.1 2.74 2.2 0.7 2.0

(1)

nF

where n is the number of inserted Li ions, F is the Faraday constant, ELi is the total energy per formula of lithium crystal, EM is that of the delithiation organic molecular crystal, and ELinM is that of the lithiation organic molecular crystal. For the nine reported organic materials, their average experimental potentials and theoretical counterparts are shown in Figure 2 with colored bars, in which the greens are

II. CALCULATION METHODS The dispersion-corrected density functional theory (DFT-D) calculation is performed using the VASP (Vienna Ab initio Simulation Package)18 code, in which the D2 correction has been used. The projected-augmented wave (PAW)29 approach was applied to treat the ion−electron interactions. The exchange-correlation energy of electrons was described in the generalized gradient approximation (GGA) with the functional parametrization of PBE.30 The energy cutoff was set at 400 eV, and a criterion of at least 0.0001 eV/atom was placed on the self-consistent convergence of the total energy.

no

E LinM − EM − nE Li

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Figure 3. Theoretical potentials of the 31 organic materials.

Figure 4. Theoretical capacity of 40 organic materials.

There are 14 organic materials’ calculated redox potentials higher than 2.0 V. As in the above discussion, although 2,3butanedione (C4H6O2, CABBIQ) has a high capacity, it is a liqiud at room temperature and cannot be used as the electrode material. The capacities of o-benzoquinone (C6H4O2, OBNZQU) and p-benzoquinone (C6H4O2, BNZQUI) are both 496 mAh/g, which is a high value. The high capacity and high potential are the positive factors for two organic compounds to be cathode materials, but their calculated band gaps of the lithiated state are 2.7 and 2.3 eV, respectively. Considering that the DFT always obviously underestimates the band gap, the present theoretical band gap, 2.7 (or 2.3) eV, is a large value, which may lower their electronic conductivity and dynamics performance in a Li battery. The capacity of 2,5-dimethyl-1,4benzoquinone (C8H8O2, DMEBQU) is 394 mAh/g, which is lower than that of the two above organic materials. At the same time, its band gap decreases to 1.7 eV, and the smaller gap may improve the electronic conductivity and dynamics performance.

(C4H6O2, CABBIQ) has a very high theoretical capacity, 623 mAh/g. Unfortunately, due to the small weight and nonpolarity, it is a liquid at ambient and cannot be used as electrode material. When considering the molecular weight and polarity, the capacity of the organic material would not be higher than 600 mAh/g (all of the capacities referred in the paper are the theoretical capacities). The band gaps of the organic materials are listed in Figure 5, in which the red bars represent the delithiated states, and the blue bars represent the lithiated states. For each material, the value of the band gap of the delithiated state is obviously different from that of the lithiated state, which is mainly due to the inserted lithium ions largely changing the interaction between the organic molecules. A good organic cathode material for a lithium battery requires a large potential, a high capacity, and a small band gap. In Figure 6, the x and y axes are, respectively, for the potential and capacity, and all of the 40 organic materials are presented. 25772


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Figure 5. Band gaps of the organic materials.

Figure 6. Capacities and potentials of the 40 organic materials.

capacity, but its band gap of the lithiated state is 3.2 eV, which is too large for the electrode material. Benzocyclobutene-1,2dione (C8H4O2, BZCBUO) and 2,5-dihydroxy-1,4-benzoquinone (C6H4O4, DHXBZQ) also have high capacities (about 400 mAh/g), and moderate band gaps (between 1.0 and 2.0 eV). Eight organic compounds are in the rectangle. (C8H8O4, ZOSYAH),33 (C22H10O4, YOFROB),34 (C14H8O5·H2O, QEGNEV),32 (C16H8O8N2S2Na2, INDIGO),36 and (Li2C18O8H12· 4H2O, PACWUN)12 have been experimentally reported. ZOSYAH has a relatively high capacity, and its band gap of the lithiated state is 3.3 eV, which is too large for the Li batteries cathode material. YOFROB also has a relatively high capacity, although there is no band gap in the lithiated state; the gap for delithiation is 1.6 eV, which may limit the dynamic performance. The capacity of QEGNEV is 196 mAh/g, the theoretical potential is 1.6 V, and the two band gaps (lithiation/ delithiation) are both 1.2 eV, all of which are the moderate values. The theoretical potential of INDIGO is 1.94 V, and the delithiation/lithiation are 0.534 and 1.267 eV, respectively.

There are 11 organic materials concentrated in the ellipse specified in Figure 6, and their capacities are all in the range from 200 to 300 mAh/g, in which 7,7,8,8-tetracyanoquinodimethane (TCYQME)31 and 1,10-phenanthroline-5,6-dione (MEJWED)35 have been experimentally reported. Most of them have a band gap (the lithiated or delithiated state) of about 2.0 eV, and as in the above discussion, it is an ideal value. Here, we highlight two materials, 2-(2-(phenyl)ethenyl)-(1,4)benzoquinone (C14H10O2, SUQDEN) and 7,9-dithiabicyclo(4.3.0)-nona-1(6),3-diene-2,5-dione-8-thione (C7H2S3O2, NUXGIW). The band gaps of SUQDEN are 0.7 eV in the delithiated state and 0.8 eV in the lithiated state, respectively; the two gap values of NUXGIW are 0.3 and 0.8 eV, respectively. The two organic compounds have relatively high capacities, high potentials, and small band gaps, which implies that they may be the proper candidates for the electrode material of Li batteries. There are 11 organic materials’ calculated redox potentials in the range from 1.5 to 2.0 V. From the former discussion, tetrahydrofuran-3,4-dione (C4H4O3, HYFURN) has a high 25773


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LiO3N tetrahedrons are co-cornered, and the tetrahedrons form a complex one-dimensional chain along the b direction. In some organic crystals, the lithium ions and oxygen ions could not form a long chain. As shown in Figure 8b, for PACWUN, each lithium ion contacts four neighboring oxygen atoms, which belongs to two different neighboring molecules and two neighboring water molecules, respectively. Here, the Li-O chain is not formed, and the strong ionic Li−O bond largely strengthens the interaction between the organic molecules. If the inserted lithium is only coordinated with one oxygen atom (only forms single Li−O bond with a neighboring organic molecule), such as 3,4-dipyrrolidino-3-cyclobutene-1,2-dione (C12H16N2O2, GAHMEH) and diphenyl 1,2-benzenedicarboxylate (C20H14O4, ACOVUK), the redox reacion is difficult to take place, which induces a low potential. For GAHMEH, the potential is 0.01 V; and for ACOVUK, the potential is 0.3 V. As referring to the crystalline structure, some organic compounds, in which lithium is coordinated with one oxygen (as shown in Figure 9), could be excluded from the cathode materials. Compared with the inorganic crystal, the distance between two neighboring molecules is too large in the organic crystal, and interaction between molecules is mainly attributed to the van der Waals force. Usually, electron hopping between neighboring molecules is difficult. In some cases, the electron maybe is delocalized in some special directions due to the molecular orientation in the crystal formation, and then some organic molecular crystals could be a semiconductor or low dimensional metal. In the Li battery, the electrode material’s electronic conductivity is one of the key factors to determine the performance. In the present work, for most materials, the lithiated and delithiated states are both semiconductors. Here, the DOS (density of states) of TCBENQ is presented in Figure 10, in which α, β, and γ are three states around the Fermi level. For the delithiated state, the α state is occupied, which is the VBM (valence band maximum), β and γ states are unoccupied, and β is the CBM (conductor band minimum). The band gap is between α and β. For the lithiated state, the β state is occupied and becomes the VBM, and γ changes to the CBM at the same time; the band gap is between β and γ. QAHREY has another kind of DOS, as shown in Figure 11. The delithiated state is obviously a semiconductor. For the lithiated state, the β state is not fully occupied, and there is no band gap, which demonstrates that it is a metal phase with high electronic conductivity. We hope to find the cathode material with no band gap in both the lithiated and the delithiated states, and the schematic diagram is shown in Figure 12. For the delithiation state, the α state is partially occupied, and β and γ states are unoccupied. For the lithiated state, the α state is fully occupied, the β state is partially occupied, and the γ state is unoccupied. Until now, although this kind of material has not been found, there is a great possibility of its existence. In this work, four organic electrode materials (with a relatively high potential, high capacity, and small band gap), BAKGOJ, MEHROH, SUQDEN and NUXGIW, are highlighted from 31 organic crystallographic structures which are selected from the CCDC database. More organic electrode materials can be developed with the present theoretical method. Although, for the method, the VDW interaction is semi-empirically calculated and the phonon influence is not

However, it has a relatively lower capacity. The band gaps of PACWUN are 0.8 eV (lithiation) and 1.2 eV (delithiation), which both are moderate values, while the capacity is too low. In the rectangle region, two compounds are highlighted, 6nitro-2,3-dihydroxyquinoxaline monohydrate (C8H7O5N3, BAKGOJ) and N-benzylindole-2,3-dione (C15H11O2N, MEHROH), both of which have small band gaps. For the former, the band gaps of the lithiation and delithiation are 0 and 0.5 eV, respectively; for the later, the two gaps are 0.3 and 0.4 eV, respectively. There are 14 organic materials’ potentials lower than 1.5 V, in which one compounds is experimentally reported, diethyl pyridine-2,6-dicarboxylate (C11H13O4N, DELXUO). Because of the low potential, those compounds may be applied in the anode material. The lithiated/delithiated process could be simply understood as the redox reaction between the CO (or CN) group and lithium, and for example, the redox process in pentacene5,7,12,14-tetraone (YOFROB) is expressed as

In that way, the reaction seems to happen just around a single molecule, and each lithium only interacts with an oxygen atom. In fact, the three-dimensional periodic crystal structure plays an important role during the process. As shown in Figure 7a, for YOFROB, each inserted Li ion is coordinated with two

Figure 7. Molecular structures of (a) YOFROB and (c) QAHERY. The crystal structure of the lithiated (b) YOFROB and (d) QAHERY.

oxygen atoms from the two neighboring molecules, and it is clearly that the one-dimensional Li-O-Li-O chain is formed in the crystal. In some organic crystals, lithium is coordinated with more oxygen atoms, such as QAHREY (Figure 7d). In the crystal, there are two types of lithium, and the first one is coordinated with four oxygen atoms, the second with three oxygen atoms and a nitrogen atom. The neighboring distortional LiO4 and 25774


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Figure 8. (a) The molecular structure of PACWUN. (b) The crystal structure of the lithiated PACWUN.

Figure 9. Molecular structure of ACOVUK (a) and GAHMEH (c). The crystal structure of the lithiated ACOVUK (b) and GAHMEH (d).

Figure 10. DOS of the lithiated/delithiated TCBENQ.

base, are investigated. The potentials range from 0.01 eV to 2.76 V, the capacities distribute from 150 to 623 Ah·kg−1, and most of the band gaps are smaller than 2.5 eV. Not only the molecular structure but also the organic crystallographic structure plays a key role for lithium storage. The inserted lithium and their coordinated oxygen form a complicated one- or two-dimensional inorganic structure and largely strengthen the molecular interaction. When the lithium is coordinated with only one oxygen atom, the redox reaction is difficult to take place and with a low potential. The materials

considered, it is still enough to search and investigate the proper organic electrode material.

IV. CONCLUSIONS The dispersion-corrected density functional theory (DFT-D2) was successfully applied to study nine reported organic electrode materials, and the results demonstrate that it is an effective method to search and investigate such material. With this method, 31 organic crystallines, which were selected from the CCDC (Cambridge Crystallographic Data Centre) data25775


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Figure 11. DOS of the lithiated/delithiated QAHREY. (5) Rao, C. V.; Reddy, A. L. M.; Ishikawa, Y.; Ajayan, P. M. LiNi1/3Co1/3Mn1/3O2-Graphene Composite As a Promising Cathode for Lithium-ion Batteries. ACS Appl. Mater. Interfaces 2011, 3, 2966− 2972. (6) Kang, K.; Meng, Y. S.; Breger, J.; Grey, C. P.; Ceder, G. Electrodes with High Power and High Capacity for Rechargeable Lithium Batteries. Science 2006, 311, 977−980. (7) Recham, N.; Chotard, J. N.; Dupont, L.; Delacourt, C.; Walker, W.; Armand, M.; Tarascon, J. M. A 3.6 V Lithium-based Fluorosulphate Insertion Positive Electrode for Lithium-ion Batteries. Nat. Mater. 2010, 9, 68−74. (8) Lupi, C.; Pasquali, M.; Dell'Era, A. Nickel and Cobalt Recycling from Lithiumion Batteries by Electrochemical Processes. Waste Manage. 2005, 25, 215−220. (9) Chen, H.; Armand, M.; Demailly, G.; Dolhem, F.; Poizot, P.; Tarascon, J. M. From Biomass to a Renewable LixC6O6 Organic Electrode for Sustainable Li-Ion Batteries. ChemSusChem 2008, 1, 348−355. (10) Song, Z.; Zhou, H. Towards Sustainable and Versatile Energy Storage Devices: an Overview of Organic Electrode Materials. Energy Environ. Sci. 2013, 6, 2280−2301. (11) Chen, H.; Armand, M.; Courty, M.; Grey, C. P.; Dolhem, F.; Tarascon, J.-M.; Poizot, P.; Jiang, M. Lithium Salt of Tetrahydroxybenzoquinone: Toward the Development of a Sustainable Li-Ion Battery. J. Am. Chem. Soc. 2009, 131, 8984−8988. (12) Walker, W.; Grugeon, S.; Mentre, O.; Laruelle, S.; Tarascon, J. M.; Wudl, F. Ethoxycarbonyl-Based Organic Electrode for Li-Batteries. J. Am. Chem. Soc. 2010, 132, 6517−6523. (13) Zhou, W.; Hernandez-Burgos, K.; Burkhardt, S. E.; Qian, H.; Abruna, H. D. Synthesis and Electrochemical and Computational Analysis of Two New Families of Thiophene-Carbonyl Molecules. J. Phys. Chem. C 2013, 117, 6022−6032. (14) Nokami, T.; Matsuo, T.; Inatomi, Y.; Hojo, N.; Tsukagoshi, T.; Yoshizawa, H.; Shimizu, A.; Kuramoto, H.; Komae, K.; Tsuyama, H.; Yoshida, J. Polymer-Bound Pyrene-4,5,9,10-tertraone for Fast-Charge and − Discharge Lithium-Ion Batteries with High Capacity. J. Am. Chem. Soc. 2012, 134, 19694−19700. (15) Karlsson, C.; Jamstorp, E.; Strømme, M.; Sjodin, M. Computational Electrochemistry Study of 16 Isoindole-4,-7-diones as Candidates for Organic Cathode Materials. J. Phys. Chem. C 2012, 116, 3793−3801. (16) Burkhardt, S.; Bois, J.; Tarascon, J.; Hennig, R.; Abruna, H. LiCarboxylate Anode Structure-Property Relationships from Molecular Modeling. Chem. Mater. 2013, 25, 132−141. (17) Hernandez-Burgos, K.; Burkhardt, S. E.; Rodriguez-Calero, G. G.; Hennig, R. G.; Abruna, H. D. Theoretical Studies of CarbonylBased Organic Molecules for Energy Storage Applications: The Heteroatom and Substituent Effect. J. Phys. Chem. C 2014, 118, 6046− 6051. (18) Kresse, G.; Furthmuller, J. Efficiency of Ab-initio Total Energy Calculations for Metals and Semicondouctors Using a Plane-Wave Basis Set. Comput. Mater. Sci. 1996, 6, 15−50.

Figure 12. DOS of the lithiation/delithiation.

with a relatively high potential, high capacity, and small band gap are highligthed, including BAKGOJ, MEHROH, SUQDEN, and NUXGIW, which may be further investigated in experimental research.

■

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpcc.5b08609. The table for the 40 organic materials (PDF)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel: 8610-67396480. Notes

The authors declare no competing financial interests.

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ACKNOWLEDGMENTS This work is supported by the Scientific Research Common Program of Beijing Municipal Commission of Education (KM201310005012).

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REFERENCES

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High Throughput Screening of Organic Electrode Materials for Lithium

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