An Ortho-Bisalkyloxylated Benzene-Based Fully Non-fused Electron Acceptor for Efficient Organic Photovoltaic Cells.
low cost
molecular aggregation
molecular design
non-fused acceptors
organic photovoltaic cells
Journal
Small methods
ISSN: 2366-9608
Titre abrégé: Small Methods
Pays: Germany
ID NLM: 101724536
Informations de publication
Date de publication:
24 Apr 2023
24 Apr 2023
Historique:
revised:
19
03
2023
received:
09
01
2023
medline:
24
4
2023
pubmed:
24
4
2023
entrez:
24
04
2023
Statut:
aheadofprint
Résumé
To develop the low-cost nonfullerene acceptors (NFAs), two fully non-fused NFAs (TBT-2 and TBT-6) with ortho-bis((2-ethylhexyl)oxy)benzene unit and different side chains onto thiophene-bridges are synthesized through highly efficient synthetic procedures. Both acceptors show good planarity, low optical gaps (≈1.51 eV), and deep highest occupied molecular orbital levels (≤-5.77 eV). More importantly, the single-crystal structure of TBT-2 shows compact molecular arrangement due to the existence of intramolecular interactions between adjacent aromatic units and strong π-π stacking between intermolecular terminal groups. When the two acceptors are fabricated organic photovoltaic (OPV) cells by combining with a wide optical gap polymer donor, the TBT-6 with strong crystallization forms large domain sizes in bulk heterojunction (BHJ) blend. As a result, the TBT-6-based OPV cell shows a low power conversion efficiency (PCE) of 9.53%. In contrast, the TBT-2 with proper crystallization facilitates morphological optimization in the BHJ blend. Consequently, the TBT-2-based OPV cell gives an outstanding PCE of 13.25%, which is one of the best values among OPV cells with similar optical gaps. Overall, this work provides a practical molecular design strategy for developing high-performance and low-cost electron acceptors.
Identifiants
pubmed: 37092533
doi: 10.1002/smtd.202300036
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300036Subventions
Organisme : National Natural Science Foundation of China
ID : NSFC 21835006
Organisme : National Natural Science Foundation of China
ID : 52120105005
Organisme : National Natural Science Foundation of China
ID : 21875182
Organisme : National Natural Science Foundation of China
ID : 52173023
Organisme : Beijing National Laboratory for Molecular Sciences
ID : BNLMS-CXXM-201903
Organisme : National Key Research and Development Program of China
ID : 2022YFE0132400
Organisme : Key Scientific and Technological Innovation Team Project of Shaanxi Province
ID : 2020TD-002
Organisme : 111 project 2.0
ID : BP0618008
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
a) G. Li, R. Zhu, Y. Yang, Nat. Photonics 2012, 6, 153;
b) J. Zhao, Y. Li, G. Yang, K. Jiang, H. Lin, H. Ade, W. Ma, H. Yan, Nat. Energy 2016, 1, 15027;
c) G. Yu, J. Gao, J. C. Hummelen, F. Wudl, A. J. Heeger, Science 1995, 270, 1789;
d) Y. Yang, Z. G. Zhang, H. Bin, S. Chen, L. Gao, L. Xue, C. Yang, Y. Li, J. Am. Chem. Soc. 2016, 138, 15011.
a) L. Zhu, M. Zhang, J. Xu, C. Li, J. Yan, G. Zhou, W. Zhong, T. Hao, J. Song, X. Xue, Z. Zhou, R. Zeng, H. Zhu, C. C. Chen, R. C. I. MacKenzie, Y. Zou, J. Nelson, Y. Zhang, Y. Sun, F. Liu, Nat. Mater. 2022, 21, 656;
b) R. Sun, Y. Wu, X. Yang, Y. Gao, Z. Chen, K. Li, J. Qiao, T. Wang, J. Guo, C. Liu, X. Hao, H. Zhu, J. Min, Adv. Mater. 2022, 34, 2110147;
c) C. He, Y. Pan, Y. Ouyang, Q. Shen, Y. Gao, K. Yan, J. Fang, Y. Chen, C.-Q. Ma, J. Min, C. Zhang, L. Zuo, H. Chen, Energy Environ. Sci. 2022, 15, 2537;
d) Y. Cui, Y. Xu, H. Yao, P. Bi, L. Hong, J. Zhang, Y. Zu, T. Zhang, J. Qin, J. Ren, Z. Chen, C. He, X. Hao, Z. Wei, J. Hou, Adv. Mater. 2021, 33, 2102420.
a) Y. Lin, J. Wang, Z. G. Zhang, H. Bai, Y. Li, D. Zhu, X. Zhan, Adv. Mater. 2015, 27, 1170;
b) J. Yuan, Y. Zhang, L. Zhou, G. Zhang, H.-L. Yip, T.-K. Lau, X. Lu, C. Zhu, H. Peng, P. A. Johnson, M. Leclerc, Y. Cao, J. Ulanski, Y. Li, Y. Zou, Joule 2019, 3, 1140;
c) Y. Cui, H. Yao, J. Zhang, K. Xian, T. Zhang, L. Hong, Y. Wang, Y. Xu, K. Ma, C. An, C. He, Z. Wei, F. Gao, J. Hou, Adv. Mater. 2020, 32, 1908205;
d) C. An, J. Hou, Acc. Chem. Res. 2022, 3, 540.
a) X.-L. Qiao, J. Yang, L.-H. Han, J.-D. Zhang, M.-F. Zhu, Chin. J. Polym. Sci. 2021, 39, 849;
b) F. Huang, Acta Polym. Sin. 2018, 9, 1141.
a) N. Li, I. McCulloch, C. J. Brabec, Energy Environ. Sci. 2018, 11, 1355;
b) J. Min, Y. N. Luponosov, C. Cui, B. Kan, H. Chen, X. Wan, Y. Chen, S. A. Ponomarenko, Y. Li, C. J. Brabec, Adv. Energy Mater. 2017, 7, 1700465;
c) J. Ren, P. Bi, J. Zhang, J. Liu, J. Wang, Y. Xu, Z. Wei, S. Zhang, J. Hou, Natl Sci Rev 2021, 8, nwab031.
S. Li, L. Zhan, F. Liu, J. Ren, M. Shi, C. Z. Li, T. P. Russell, H. Chen, Adv. Mater. 2018, 30, 1705208.
Y. Zhou, M. Li, H. Lu, H. Jin, X. Wang, Y. Zhang, S. Shen, Z. Ma, J. Song, Z. Bo, Adv. Funct. Mater. 2021, 31, 2101742.
a) X. Zhang, C. Li, L. Qin, H. Chen, J. Yu, Y. Wei, X. Liu, J. Zhang, Z. Wei, F. Gao, Q. Peng, H. Huang, Angew. Chem., Int. Ed. 2021, 60, 17720;
b) X. Zhang, L. Qin, J. Yu, Y. Li, Y. Wei, X. Liu, X. Lu, F. Gao, H. Huang, Angew. Chem., Int. Ed. 2021, 60, 12475;
c) C. He, Y. Li, S. Li, Z. P. Yu, Y. Li, X. Lu, M. Shi, C. Z. Li, H. Chen, ACS Appl. Mater. Interfaces 2020, 12, 16700;
d) Z. Yao, Y. Li, S. Li, J. Xiang, X. Xia, X. Lu, M. Shi, H. Chen, ACS Appl. Energy Mater. 2020, 4, 819;
e) H. Huang, Q. Guo, S. Feng, C. Zhang, Z. Bi, W. Xue, J. Yang, J. Song, C. Li, X. Xu, Z. Tang, W. Ma, Z. Bo, Nat. Commun. 2019, 10, 3038.
a) T. J. Wen, Z. X. Liu, Z. Chen, J. Zhou, Z. Shen, Y. Xiao, X. Lu, Z. Xie, H. Zhu, C. Z. Li, H. Chen, Angew. Chem., Int. Ed. 2021, 60, 12964;
b) Z. P. Yu, Z. X. Liu, F. X. Chen, R. Qin, T. K. Lau, J. L. Yin, X. Kong, X. Lu, M. Shi, C. Z. Li, H. Chen, Nat. Commun. 2019, 10, 2152.
Z. X. Liu, Z. P. Yu, Z. Shen, C. He, T. K. Lau, Z. Chen, H. Zhu, X. Lu, Z. Xie, H. Chen, C. Z. Li, Nat. Commun. 2021, 12, 3049.
Y. Wang, Z. Liu, X. Cui, C. Wang, H. Lu, Y. Liu, Z. Fei, Z. Ma, Z. Bo, J. Mater. Chem. A 2020, 8, 12495.
a) H. Lu, X. Wang, H. Wang, A. Zhang, X. Zheng, N. Yu, Z. Tang, X. Xu, Y. Liu, Y.-N. Chen, Z. Bo, Sci China Chem 2022, 65, 594;
b) L. Ma, S. Zhang, J. Zhu, J. Wang, J. Ren, J. Zhang, J. Hou, Nat. Commun. 2021, 12, 5093;
c) J. Hou, O. Inganas, R. H. Friend, F. Gao, Nat. Mater. 2018, 17, 119.
X. Wang, H. Lu, Y. Liu, A. Zhang, N. Yu, H. Wang, S. Li, Y. Zhou, X. Xu, Z. Tang, Z. Bo, Adv. Energy Mater. 2021, 11, 2102591.
X. Zheng, W. Liu, H. Lu, N. Yu, Y. Wang, H. Huang, S. Li, X. Wang, H. Wang, Y. Liu, X. Xu, Z. Tang, Z. Bo, Chem. Eng. J. 2022, 444, 136472.
J. Zhu, C. Yang, L. Ma, T. Zhang, S. Li, S. Zhang, H. Fan, J. Hou, Org. Electron. 2022, 105, 106512.
a) T. Li, Y. Wu, J. Zhou, M. Li, J. Wu, Q. Hu, B. Jia, X. Pan, M. Zhang, Z. Tang, Z. Xie, T. P. Russell, X. Zhan, J. Am. Chem. Soc. 2020, 142, 20124;
b) F. Lin, K. Jiang, W. Kaminsky, Z. Zhu, A. K. Jen, J. Am. Chem. Soc. 2020, 142, 15246.
R. Hou, M. Li, X. Ma, H. Huang, H. Lu, Q. Jia, Y. Liu, X. Xu, H. B. Li, Z. Bo, ACS Appl. Mater. Interfaces 2020, 12, 46220.
C. Li, J. Zhou, J. Song, J. Xu, H. Zhang, X. Zhang, J. Guo, L. Zhu, D. Wei, G. Han, J. Min, Y. Zhang, Z. Xie, Y. Yi, H. Yan, F. Gao, F. Liu, Y. Sun, Nat. Energy 2021, 6, 605.
T. J. Aldrich, M. Matta, W. Zhu, S. M. Swick, C. L. Stern, G. C. Schatz, A. Facchetti, F. S. Melkonyan, T. J. Marks, J. Am. Chem. Soc. 2019, 141, 3274.
W. Zhao, S. Li, H. Yao, S. Zhang, Y. Zhang, B. Yang, J. Hou, J. Am. Chem. Soc. 2017, 139, 7148.
T. Zhang, C. An, Y. Cui, J. Zhang, P. Bi, C. Yang, S. Zhang, J. Hou, Adv. Mater. 2021, 34, 2105803.
R. Po, J. Roncali, J. Mater. Chem. C 2016, 4, 3677.
P. Schilinsky, C. Waldauf, C. J. Brabec, Appl. Phys. Lett. 2002, 81, 3885.
S. R. Cowan, A. Roy, A. J. Heeger, Phys. Rev. B 2010, 82, 245207.
a) H. Hu, K. Jiang, P. C. Y. Chow, L. Ye, G. Zhang, Z. Li, J. H. Carpenter, H. Ade, H. Yan, Adv. Energy Mater. 2017, 8, 1701674;
b) P. Wan, C. An, T. Zhang, K. Ma, N. Liang, Y. Xu, S. Zhang, B. Xu, J. Zhang, J. Hou, Poly. Chem. 2020, 11, 1629.
L. Ye, H. Hu, M. Ghasemi, T. Wang, B. A. Collins, J. H. Kim, K. Jiang, J. H. Carpenter, H. Li, Z. Li, T. McAfee, J. Zhao, X. Chen, J. L. Y. Lai, T. Ma, J. L. Bredas, H. Yan, H. Ade, Nat. Mater. 2018, 17, 253.
L. Ma, H. Yao, J. Wang, Y. Xu, M. Gao, Y. Zu, Y. Cui, S. Zhang, L. Ye, J. Hou, Angew. Chem., Int. Ed. 2021, 60, 15988.
K. M. Katubi, A. M. S. Pembere, M. Y. Mehboob, M. S. Al-Buriahi, Int. J. Quantum Chem. 2022, 122, e26998.