J. Semicond. > 2021, Volume 42 > Issue 6 > 060501

SHORT COMMUNICATION

Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels

Xiongfeng Li1, 2, Jingui Xu2, 3, Zuo Xiao2, , Xingzhu Wang1, , Bin Zhang3, and Liming Ding2,

+ Author Affiliations

 Corresponding author: Zuo Xiao, xiaoz@nanoctr.cn; Xingzhu Wang, xzwang@xtu.edu.cn; Bin Zhang, msbinzhang@outlook.com; Liming Ding, ding@nanoctr.cn

DOI: 10.1088/1674-4926/42/6/060501

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Star nonfullerene acceptors like ITIC[1], IDIC[2], O-IDTBR[3], IT-4F[4], COi8DFIC[5], Y6[6] etc. continuously emerge and keep pushing the power conversion efficiency (PCE) of organic solar cells forward. These small molecules generally show narrow bandgaps, excellent visible to NIR light-harvesting capability, good electron mobility, suitable energy levels and miscibility with the donor materials. PCEs up to 18.56% have been achieved for the state-of-the-art nonfullerene organic solar cells[7]. On the other hand, donor materials matching nonfullerene acceptors also received considerable interests[8]. Owing to complementary light absorption, high hole-mobility and deep HOMO levels, wide-bandgap (WBG) conjugated copolymers are ideal donor partners for the low-bandgap nonfullerene acceptors. Hou et al. developed a WBG copolymer donor PM6 based on a benzo[1,2-c:4,5-c']dithiophene-4,8-dione (BDD) unit[9]. PM6 has been widely applied in nonfullerene solar cells, delivering high PCEs up to 17.8%[10]. Li et al. reported a simple-structured WBG copolymer PTQ10 based on a quinoxaline unit[11]. Solar cells based on PTQ10 and Y6 gave a PCE of 16.53%[12]. Huang et al. developed a WBG copolymer P2F-EHp by using an imide-functionalized benzotrizole (TzBI) unit[13]. P2F-EHp:Y6 solar cells gave a 16.02% PCE. Guo et al. synthesized a random copolymer S1 with a fluorine and ester group functionalized thiophene (FE-T) unit[14]. Owing to the strong electron-withdrawing property of FE-T, S1 has a deep HOMO level and delivered a high open-circuit voltage (Voc) of 0.88 V and a PCE of 16.42%. Ding et al. developed a 2.16 eV ultra-WBG copolymer W1 by using a fluorinated 1,2-dialkoxybenzene (FAB) unit[15]. The FAB unit offers unique $ {\rm{S}} \cdots {\rm{O}} $ and $ {\rm{F}} \cdots {\rm{H}} $ double-side conformation locking in the copolymer backbone, and renders W1 enhanced packing and good hole-transporting capability[16]. W1:Y6 solar cells gave a PCE of 16.23%. Ding et al. also developed several high-performance WBG copolymer donors based on fused-ring acceptor units. The WBG copolymer L1 based on a fused-ring lactone unit 5H-dithieno[3,2-b:2',3'-d]pyran-5-one (DTP) delivered a 14.36% PCE[17]. A fused-ring thiolactone copolymer D16 based on the 5H-dithieno[3,2-b:2',3'-d]thiopyran-5-one (DTTP) unit gave a higher PCE of 16.72%[18]. By using a dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]thiadiazole (DTBT) unit, which has a larger molecular plane than DTP and DTTP, Ding et al. developed a more efficient WBG copolymer donor D18[19]. D18:Y6 solar cells gave a PCE of 18.22% (certified 17.6%). This is the first time for the PCE of OSCs surpassing 18%. Thick-film D18:Y6:PC61BM ternary cells delivered 16% PCEs with an active layer thickness over 300 nm[20]. Ding et al. further reported a chlorinated analogue of D18, the D18-Cl[21]. Blending D18-Cl with a nonfullerene acceptor N3 yielded a PCE of 18.13% (certified 17.6%). Very recently, Ding et al. pushed the PCE to 18.56% (certified 17.9%) by blending D18 with N3, setting a new PCE record[7]. These works demonstrated the advantages of fused-ring acceptor units in constructing WBG copolymer donors. The strong electron-withdrawing capability and extended molecular planes of these acceptor units gift copolymers deep HOMO levels, enhanced packing and high hole mobility, thus leading to improved Voc, short-circuit current density (Jsc) and fill factor (FF) in solar cells. In this work, we report copolymers P1 and P2 based on a dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole (DTBO) unit (Fig. 1(a)). Compared with DTBT, DTBO has fewer synthetic steps and is more cost-effective[22]. DFT calculations indicate that DTBO renders the copolymer a deeper HOMO level, thus yielding higher Voc in solar cells. Solar cells with P1 and P2 as the donors and Y6 as the acceptor afforded high Voc up to 0.91 V and decent PCEs up to 15.64%.

Figure  1.  (Color online) (a) DTBT and DTBO building blocks, and DTBO-based copolymers P1 and P2. (b) Molecular models and corresponding frontier molecular orbitals and energy levels for D18, P1 and P2. (c) J–V curves for P1:Y6 and P2:Y6 solar cells. (d) EQE spectra for P1:Y6 and P2:Y6 solar cells.

We built the polymer models for D18, P1 and P2 (Fig. 1(b)). Each model has two repeating units, and the alkyl chains were replaced by methyl groups for saving the calculation time. All structures were optimized at the B3LYP/6-31G(d) level. The DFT-predicted frontier molecular orbitals and energy levels for D18, P1 and P2 are shown in Fig. 1(b). From D18 to P1, DTBT being replaced by DTBO, simultaneous decrease in HOMO and LUMO energy levels was observed. The HOMO and LUMO levels for P1 are –5.05 and –2.69 eV, respectively, which are ~0.1 eV lower than that of D18. A higher Voc was expected for P1-based solar cells since Voc is proportional to the energy difference between donor HOMO and acceptor LUMO[23]. Compared with P1, P2 shows higher HOMO and LUMO levels of –4.94 and –2.61 eV, respectively, due to the removal of electron-withdrawing fluorine atoms. For P1 and P2, the variation trends in DFT-predicted HOMO and LUMO levels are consistent with those from cyclic voltammetry (CV) measurements (vide infra).

The synthetic routes for P1 and P2 are shown in Scheme S1. The 5,8-dibromodithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole (DTBO-Br) coupled with tributyl(4-(2-butyloctyl)thiophen-2-yl)stannane gave compound 1 in 62% yield. Bromination of compound 1 with NBS gave compound 2 in 80% yield. Copolymerization of compound 2 with (4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) (FBDT-Sn) and (4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane) (BDT-Sn) gave P1 and P2 in 90% and 58% yield, respectively. The number-average molecular weights (Mn) for P1 and P2 are 38.0 and 47.0 kDa, respectively, with the polydispersity indexes (PDI) of 2.08 and 1.67, respectively. P1 and P2 are soluble in chloroform and chlorobenzene. The absorption spectra for P1, P2 and Y6 films are shown in Fig. S7. Both P1 and P2 show two absorption peaks, with a high-energy peak at 545 and 549 nm, respectively, and a low-energy peak at 582 and 590 nm, respectively. The absorption band for P1 and P2 lies in 400–620 nm region, which is complementary with that of Y6 (560–920 nm). The absorption onsets for P1 and P2 films are 626 and 633 nm, respectively, corresponding to optical bandgaps (Egopt) of 1.98 and 1.96 eV, respectively. Energy levels for P1 and P2 were estimated from CV measurements (Fig. S8). The HOMO and LUMO levels for P1 and P2 were calculated from the onset potentials of oxidation (Eonox) and reduction (Eonred), respectively, i.e., HOMO = –(Eonox + 4.8) and LUMO = –(Eonred + 4.8). The energy level diagram is presented in Fig. S9. P1 and P2 show deep HOMO levels of –5.61 and –5.45 eV, respectively, which are favorable for producing high Voc in solar cells. The HOMO level of P1 is 0.1 eV deeper than that of D18 (–5.51 eV)[19], consisting with DFT calculation.

Solar cells with a structure of ITO/PEDOT:PSS/polymer:Y6/PDIN/Ag were made to evaluate the performance of P1 and P2. The D/A ratio, active layer thickness and additive (1-chloronaphthalene) content were optimized (Tables S1–S6). J–V curves and external quantum efficiency (EQE) spectra for the best cells are shown in Figs. 1(c) and 1(d), respectively. The best P1:Y6 cells gave a PCE of 10.92%, with a Voc of 0.91 V, a Jsc of 18.22 mA cm–2 and a FF of 65.7%. These cells have a D/A ratio of 1 : 1.6 (w/w), an active layer thickness of 110 nm and no additive. The best P2:Y6 cells gave a PCE of 15.64%, with a Voc of 0.83 V, a Jsc of 26.72 mA cm–2 and a FF of 70.6%. These cells have a D/A ratio of 1 : 1.6 (w/w), an active layer thickness of 120 nm and no additive. The Voc of P1:Y6 cells is 0.05 V higher than that of D18:Y6 cells[19], suggesting the advantage of DTBO unit in enhancing Voc. The P2:Y6 cells present much better performance than P1:Y6 cells due to the higher Jsc and FF. P2 cells afforded higher EQE than P1 cells in the whole spectrum, with the maximum EQE of 86% at 560 nm (Fig. 1(d)). The integrated current densities for P1 and P2 cells are 17.56 and 25.75 mA cm–2, respectively, consistent with Jsc from J–V measurements. The exciton dissociation probabilities (Pdiss) for P1 and P2 cells are 96.3% and 98.4%, respectively, suggesting more efficient carrier generation in the latter (Fig. S10)[24]. Higher Jsc and FF for P2 cells suggest a superior charge-transporting capability of P2. Hole mobilities (μh) were measured for pure P1 and P2 films by using space-charge limited current (SCLC) method (Fig. S11)[25-27]. The μh for P1 and P2 are 5.13 × 10–4 and 8.82 × 10–4 cm2 V–1 s–1, respectively, confirming the better hole-transporting capability of P2. The μh and the electron mobilities (μe) were also measured for the blend films (Figs. S12 and S13). Compared with P1:Y6 film, P2:Y6 film gave a higher μh of 3.92 × 10–4 cm2 V–1 s–1, a higher μe of 2.97 × 10–4 cm2 V–1 s–1, and a smaller μh/μe of 1.32 (Table S7). We investigated bimolecular recombination by plotting Jsc against light intensity (Plight) (Fig. S14)[28-31]. P2:Y6 cells showed a α value of 0.985, which is closer to 1 than that of P1:Y6 cells (0.973), suggesting less bimolecular recombination in P2:Y6 cells. The faster and more balanced charge transport as well as less charge recombination in P2:Y6 cells account for the higher FF. The morphology for P1:Y6 and P2:Y6 blend films was studied by using atomic force microscope (AFM) (Fig. S15). Both films present nanofiber structures. Compared with P1:Y6 film, P2:Y6 film has a smoother surface. The root-mean-square roughnesses for P1:Y6 and P2:Y6 films are 1.20 and 1.02 nm, respectively.

In summary, a fused-ring acceptor unit DTBO was developed. Compared with previously reported DTBT unit, DTBO can lower the HOMO level of polymer donors, thus increasing the Voc of solar cells. DTBO-based copolymers delivered a maximum Voc of 0.91 V and a maximum PCE of 15.64%.

This work was supported by the National Key Research and Development Program of China (2017YFA0206600, SQ2020YFE010701), the National Natural Science Foundation of China (51773045, 21772030, 51922032, 21961160720, 51473053) and the Natural Science Foundation of Hunan Province (2019JJ50603).

Supplementary materials to this article can be found online at https://doi.org/1674-4926/42/6/060501https://doi.org/1674-4926/42/6/060501.



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Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Energy Environ Sci, 2016, 9, 2114 doi: 10.1039/C6EE01026A
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Fig. 1.  (Color online) (a) DTBT and DTBO building blocks, and DTBO-based copolymers P1 and P2. (b) Molecular models and corresponding frontier molecular orbitals and energy levels for D18, P1 and P2. (c) J–V curves for P1:Y6 and P2:Y6 solar cells. (d) EQE spectra for P1:Y6 and P2:Y6 solar cells.

[1]
Lin Y, Wang J, Zhang Z, et al. An electron acceptor challenging fullerenes for efficient polymer solar cells. Adv Mater, 2015, 27, 1170 doi: 10.1002/adma.201404317
[2]
Lin Y, He Q, Zhao F, et al. A facile planar fused-ring electron acceptor for as-cast polymer solar cells with 8.71% efficiency. J Am Chem Soc, 2016, 138, 2973 doi: 10.1021/jacs.6b00853
[3]
Holliday S, Ashraf R S, Wadsworth A, et al. High-efficiency and air-stable P3HT-based polymer solar cells with a new non-fullerene acceptor. Nat Commun, 2016, 7, 11585 doi: 10.1038/ncomms11585
[4]
Zhao W, Li S, Yao H, et al. Molecular optimization enables over 13% efficiency in organic solar cells. J Am Chem Soc, 2017, 139, 7148 doi: 10.1021/jacs.7b02677
[5]
Xiao Z, Liu F, Geng X, et al. A carbon-oxygen-bridged ladder-type building block for efficient donor and acceptor materials used in organic solar cells. Sci Bull, 2017, 62, 1331 doi: 10.1016/j.scib.2017.09.017
[6]
Yuan J, Zhang Y, Zhou L, et al. Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core. Joule, 2019, 3, 1140 doi: 10.1016/j.joule.2019.01.004
[7]
Jin K, Xiao Z, Ding L. D18, an eximious solar polymer!. J Semicond, 2021, 42, 010502 doi: 10.1088/1674-4926/42/1/010502
[8]
Tong Y, Xiao Z, Du X, et al. Progress of the key materials for organic solar cells. Sci China Chem, 2020, 63, 758 doi: 10.1007/s11426-020-9726-0
[9]
Zhang M, Guo X, Ma W, et al. A large-bandgap conjugated polymer for versatile photovoltaic applications with high performance. Adv Mater, 2015, 27, 4655 doi: 10.1002/adma.201502110
[10]
Cui Y, Yao H, Zhang J, et al. Single-junction organic photovoltaic cells with approaching 18% efficiency. Adv Mater, 2020, 32, 1908205 doi: 10.1002/adma.201908205
[11]
Sun C, Pan F, Bin H, et al. A low cost and high performance polymer donor material for polymer solar cells. Nat Commun, 2018, 9, 743 doi: 10.1038/s41467-018-03207-x
[12]
Wu Y, Zheng Y, Yang H, et al. Rationally pairing photoactive materials for high-performance polymer solar cells with efficiency of 16.53%. Sci China Chem, 2020, 63, 265 doi: 10.1007/s11426-019-9599-1
[13]
Lan L, Chen Z, Hu Q, et al. High-performance polymer solar cells based on a wide-bandgap polymer containing pyrrolo[3,4-f] benzotriazole-5,7-dione with a power conversion efficiency of 8.63%. Adv Sci, 2016, 3, 1600032 doi: 10.1002/advs.201600032
[14]
Fan B, Zhang D, Li M, et al. Achieving over 16% efficiency for single-junction organic solar cells. Sci China Chem, 2019, 62, 746 doi: 10.1007/s11426-019-9457-5
[15]
Wang T, Qin J, Xiao Z, et al. A 2.16 eV bandgap polymer donor gives 16% power conversion efficiency. Sci Bull, 2020, 65, 179 doi: 10.1016/j.scib.2019.11.030
[16]
Wang T, Qin J, Xiao Z, et al. Multiple conformation locks gift polymer donor high efficiency. Nano Energy, 2020, 77, 105161 doi: 10.1016/j.nanoen.2020.105161
[17]
Liu J, Liu L, Zuo C, et al. 5H-dithieno[3,2-b:2',3'-d]pyran-5-one unit yields efficient wide-bandgap polymer donors. Sci Bull, 2019, 64, 1655 doi: 10.1016/j.scib.2019.09.001
[18]
Xiong J, Jin K, Jiang Y, et al. Thiolactone copolymer donor gifts organic solar cells a 16.72% efficiency. Sci Bull, 2019, 64, 1573 doi: 10.1016/j.scib.2019.10.002
[19]
Liu Q, Jiang Y, Jin K, et al. 18% Efficiency organic solar cells. Sci Bull, 2020, 65, 272 doi: 10.1016/j.scib.2020.01.001
[20]
Qin J, Zhang L, Xiao Z, et al. Over 16% efficiency from thick-film organic solar cells. Sci Bull, 2020, 65, 1979 doi: 10.1016/j.scib.2020.08.027
[21]
Qin J, Zhang L, Zuo C, et al. A chlorinated copolymer donor demonstrates a 18.13% power conversion efficiency. J Semicond, 2021, 42, 010501 doi: 10.1088/1674-4926/42/1/010501
[22]
Lee J, Sin D H, Clement J A, et al. Medium-bandgap conjugated polymers containing fused dithienobenzochalcogenadiazoles: Chalcogen atom effects on organic photovoltaics. Macromolecules, 2016, 49, 9358 doi: 10.1021/acs.macromol.6b01569
[23]
Rand B P, Burk D P, Forrest S R. Offset energies at organic semiconductor heterojunctions and their influence on the open-circuit voltage of thin-film solar cells. Phys Rev B, 2007, 75, 115327 doi: 10.1103/PhysRevB.75.115327
[24]
Xiong J, Xu J, Jiang Y, et al. Fused-ring bislactone building blocks for polymer donors. Sci Bull, 2020, 65, 1792 doi: 10.1016/j.scib.2020.07.018
[25]
Xiao Z, Geng X, He D, et al. Development of isomer-free fullerene bisadducts for efficient polymer solar cells. Energy Environ Sci, 2016, 9, 2114 doi: 10.1039/C6EE01026A
[26]
Gao Y, Li D, Xiao Z, et al. High-performance wide-bandgap copolymers with dithieno[3,2-b:2',3'-d]pyridin-5(4H)-one units. Mater Chem Front, 2019, 3, 399 doi: 10.1039/C8QM00604K
[27]
Deng L, Li X, Wang S, et al. Stereomeric effects of bisPC71BM on polymer solar cell performance. Sci Bull, 2016, 61, 132 doi: 10.1007/s11434-015-0979-5
[28]
Wang J, Gao Y, Xiao Z, et al. A wide-bandgap copolymer donor based on a phenanthridin-6(5H)-one unit. Mater Chem Front, 2019, 3, 2686 doi: 10.1039/C9QM00622B
[29]
Zhang L, Jin K, Xiao Z, et al. Alkoxythiophene and alkylthiothiophene π-bridges enhance the performance of A-D-A electron acceptors. Mater Chem Front, 2019, 3, 492 doi: 10.1039/C8QM00647D
[30]
Jin K, Deng C, Zhang L, et al. A heptacyclic carbon-oxygen-bridged ladder-type building block for A-D-A acceptors. Mater Chem Front, 2018, 2, 1716 doi: 10.1039/C8QM00285A
[31]
Li W, Liu Q, Jin K, et al. Fused-ring phenazine building blocks for efficient copolymer donors. Mater Chem Front, 2020, 4, 1454 doi: 10.1039/D0QM00080A

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    Received: 18 March 2021 Revised: Online: Accepted Manuscript: 18 March 2021Uncorrected proof: 18 March 2021Published: 01 June 2021

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      Xiongfeng Li, Jingui Xu, Zuo Xiao, Xingzhu Wang, Bin Zhang, Liming Ding. Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. Journal of Semiconductors, 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501 ****X F Li, J G Xu, Z Xiao, X Z Wang, B Zhang, L M Ding, Dithieno[3\',2\':3,4;2\'\',3\'\':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. J. Semicond., 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501.
      Citation:
      Xiongfeng Li, Jingui Xu, Zuo Xiao, Xingzhu Wang, Bin Zhang, Liming Ding. Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. Journal of Semiconductors, 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501 ****
      X F Li, J G Xu, Z Xiao, X Z Wang, B Zhang, L M Ding, Dithieno[3\',2\':3,4;2\'\',3\'\':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels[J]. J. Semicond., 2021, 42(6): 060501. doi: 10.1088/1674-4926/42/6/060501.

      Dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]oxadiazole-based polymer donors with deep HOMO levels

      DOI: 10.1088/1674-4926/42/6/060501
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      • Xiongfeng Li:got his BS degree from Xiangtan University. Now he is a master student at Xiangtan University under the supervision of Professor Xingzhu Wang. Since September 2019, he has been working in Liming Ding Lab at National Center for Nanoscience and Technology as a visiting student. His work focuses on organic solar cells
      • Jingui Xu:got his BS degree from Yancheng Institute of Technology. Now he is a master student at Changzhou University under the supervision of Professor Bin Zhang. Since September 2019, he has been working in Liming Ding Lab at National Center for Nanoscience and Technology as a visiting student. His work focuses on organic solar cells
      • Zuo Xiao:got his BS and PhD degrees from Peking University under the supervision of Professor Liangbing Gan. He did postdoctoral research in Eiichi Nakamura Lab at the University of Tokyo. In March 2011, he joined Liming Ding Group at National Center for Nanoscience and Technology as an associate professor. In April 2020, he was promoted to be a full professor. His current research focuses on organic solar cells
      • Xingzhu Wang:obtained his PhD degree from Hong Kong Baptist University in 2009. After postdoctoral works at University of Cambridge and Nanyang Technological University, he worked at National University of Singapore from 2013 to 2017 as a senior research fellow and now he works at Xiangtan University and Southern University of Science and Technology as a professor. His research interests include organic synthesis, organic semiconductors and optoelectronic devices
      • Bin Zhang:got his BS degree from East China University of Technology in 2005. Then, he got his MS and PhD degrees from South China University of Technology (SCUT) in 2008 and 2012, respectively. From 2013 to 2017, he did postdoctoral research in SCUT and Shenzhen University. In 2018, he joined Changzhou University and was appointed as an associate professor. His research focuses on organic semiconductors and perovskite solar cells
      • Liming Ding:got his PhD from University of Science and Technology of China (was a joint student at Changchun Institute of Applied Chemistry, CAS). He started his research on OSCs and PLEDs in Olle Inganäs Lab in 1998. Later on, he worked at National Center for Polymer Research, Wright-Patterson Air Force Base and Argonne National Lab (USA). He joined Konarka as a Senior Scientist in 2008. In 2010, he joined National Center for Nanoscience and Technology as a full professor. His research focuses on functional materials and devices. He is RSC Fellow, the nominator for Xplorer Prize, and the Associate Editors for Science Bulletin and Journal of Semiconductors
      • Corresponding author: xiaoz@nanoctr.cnxzwang@xtu.edu.cnmsbinzhang@outlook.comding@nanoctr.cn
      • Received Date: 2021-03-18
      • Published Date: 2021-06-10

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