journal article·2024-08Open access

Tailoring Cyano Substitutions on Quinoxaline‐based Small‐Molecule Acceptors Enabling Enhanced Molecular Packing for High‐Performance Organic Solar Cells

Li Chen, Chaoyue Zhao, Han Yu, Aleksandr Sergeev, Liangxiang Zhu, Kan Ding, Yuang Fu, Ho Ming Ng, Chung Hang Kwok, Xinhui Zou, Jicheng Yi, Xinhui Lu, Kam Sing Wong, Harald Ade, Guangye Zhang, He Yan

Advanced Energy Materials· Volume 14· Issue 30

Abstract

Abstract Cyanation is a common chemical modification strategy to fine‐tune the energy levels and molecular packing of organic semiconductors, especially materials used in organic solar cells (OSCs). Generally, cyanation is used to modify the end groups of high‐performance small‐molecule acceptors (SMAs). However, the cyanation strategy has not been investigated on the central backbone of SMAs, which could introduce stronger intermolecular interaction and enhance the π–π stacking for rapid charge transport. This paper, for the first time, reports a new cyanation strategy on the central benzo‐quinoxaline core and synthesizes two novel A‐DA'D‐A type SMAs, named BQx‐CN and BQx‐2CN, with mono‐ and di‐cyanide groups, respectively. Through tailoring the number of CN groups, the BQx‐CN‐based OSC exhibits the best device performance of 18.8%, which is significantly higher than the non‐cyano BQx‐based one. The reason for the superior performance of BQx‐CN‐based devices can be attributed to the fine‐tuned energy level, stronger packing, and ideal phase segregation, which lead to superior exciton dissociation, faster charge transport, and suppressed recombination, therefore the highest fill factor (FF) and power conversion efficiencies (PCE). The research demonstrates the effectiveness of the cyanation strategy on the central core of SMAs for enhanced molecular packing and better performance of OSCs.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Perovskite Materials and Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Guangdong‐Hong Kong Joint Laboratory for Carbon Neutrality Jiangmen Laboratory of Carbon Science and Technology Jiangmen Guangdong Province 529199 China

Department of Chemistry Guangdong‐Hong Kong‐Macao Joint Laboratory of Optoelectronic and Magnetic Functional Materials Energy Institute and Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration & Reconstruction Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong 999077 China

College of New Materials and New Energies Shenzhen Technology University Shenzhen 518118 China

Hong Kong University of Science and Technology‐Shenzhen Research Institute No. 9, Yuexing 1st RD, Hi‐tech Park, Nanshan Shenzhen 518057 China

Department of Physics Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong 999077 China

Department of Physics and Organic and Carbon Electronics Laboratories (ORaCEL) North Carolina State University Raleigh NC 27695 USA

Department of Physics Chinese University of Hong Kong New Territories Hong Kong 999077 China

Funding

National Key Research and Development Program of China · Ministry of Science and Technology of the People's Republic of China · National Natural Science Foundation of China · Shenzhen Fundamental Research Program

References (73)

Show source-provided references
1. 10.1038/s41578-023-00606-510.1038/s41578-023-00606-5 ↗
2. 10.1021/acs.chemrev.1c0095510.1021/acs.chemrev.1c00955 ↗
3. 10.1038/s41560-023-01309-510.1038/s41560-023-01309-5 ↗
4. 10.1016/j.joule.2023.07.00310.1016/j.joule.2023.07.003 ↗
5. 10.1016/j.joule.2023.07.00510.1016/j.joule.2023.07.005 ↗
6. 10.1002/anie.20230830710.1002/anie.202308307 ↗
7. 10.1038/s41467-023-40423-610.1038/s41467-023-40423-6 ↗
8. 10.1002/adma.20230040010.1002/adma.202300400 ↗
9. 10.1039/D2EE03134E10.1039/D2EE03134E ↗
10. 10.1002/adma.20220208910.1002/adma.202202089 ↗
11. 10.1038/s41563-022-01244-y10.1038/s41563-022-01244-y ↗
12. 10.1002/adma.20220821110.1002/adma.202208211 ↗
13. 10.1002/adma.20230063110.1002/adma.202300631 ↗
14. 10.1002/adma.20221086510.1002/adma.202210865 ↗
15. 10.1002/adma.20210242010.1002/adma.202102420 ↗
16. 10.1039/D2EE00595F10.1039/D2EE00595F ↗
17. Meng L. · Sci. China Chem. · 2023 · 66 · 808
18. 10.1002/adma.20220898610.1002/adma.202208986 ↗
19. 10.1002/aenm.20230076310.1002/aenm.202300763 ↗
20. 10.1016/j.joule.2021.12.01710.1016/j.joule.2021.12.017 ↗
21. 10.1093/nsr/nwad08510.1093/nsr/nwad085 ↗
22. 10.1016/j.joule.2019.01.00410.1016/j.joule.2019.01.004 ↗
23. 10.1021/acsenergylett.0c0223010.1021/acsenergylett.0c02230 ↗
24. 10.1016/j.jechem.2021.05.04110.1016/j.jechem.2021.05.041 ↗
25. 10.1002/adma.20190820510.1002/adma.201908205 ↗
26. 10.1002/adma.20190632410.1002/adma.201906324 ↗
27. 10.1002/adma.20210083010.1002/adma.202100830 ↗
28. 10.1039/D3EE01333B10.1039/D3EE01333B ↗
29. 10.1016/j.scib.2022.10.00510.1016/j.scib.2022.10.005 ↗
30. 10.1016/j.mtener.2023.10136810.1016/j.mtener.2023.101368 ↗
31. 10.1021/acs.macromol.3c0141610.1021/acs.macromol.3c01416 ↗
32. 10.1038/s41467-018-03207-x10.1038/s41467-018-03207-x ↗
33. 10.1002/anie.20231975510.1002/anie.202319755 ↗
34. 10.1021/acsaem.3c0200910.1021/acsaem.3c02009 ↗
35. 10.1039/D2EE01340A10.1039/D2EE01340A ↗
36. 10.1002/anie.20220958010.1002/anie.202209580 ↗
37. 10.1039/D3EE01164J10.1039/D3EE01164J ↗
38. 10.1002/anie.20220776210.1002/anie.202207762 ↗
39. 10.1038/s41467-022-30927-y10.1038/s41467-022-30927-y ↗
40. 10.1039/D2EE03902H10.1039/D2EE03902H ↗
41. 10.1021/acs.chemmater.9b0011810.1021/acs.chemmater.9b00118 ↗
42. 10.1002/aenm.20220439410.1002/aenm.202204394 ↗
43. 10.1002/aenm.20190424710.1002/aenm.201904247 ↗
44. 10.1039/D1QM00558H10.1039/D1QM00558H ↗
45. 10.1002/aenm.20170143610.1002/aenm.201701436 ↗
46. 10.1002/adma.20190516110.1002/adma.201905161 ↗
47. 10.1021/acs.chemmater.6b0203010.1021/acs.chemmater.6b02030 ↗
48. 10.1002/anie.20211611110.1002/anie.202116111 ↗
49. 10.1021/jacs.0c0556010.1021/jacs.0c05560 ↗
50. 10.1002/adma.20150211010.1002/adma.201502110 ↗
51. 10.1038/s41467-023-36413-310.1038/s41467-023-36413-3 ↗
52. 10.1038/s41467-023-37738-910.1038/s41467-023-37738-9 ↗
53. 10.1002/adma.20211014710.1002/adma.202110147 ↗
54. 10.1038/s41563-018-0128-z10.1038/s41563-018-0128-z ↗
55. 10.1038/s41560-020-00684-710.1038/s41560-020-00684-7 ↗
56. 10.1021/jacs.8b0583410.1021/jacs.8b05834 ↗
57. 10.1021/acs.jpcc.0c0966310.1021/acs.jpcc.0c09663 ↗
58. 10.1002/anie.20201628410.1002/anie.202016284 ↗
59. 10.1002/adfm.20230071210.1002/adfm.202300712 ↗
60. 10.1016/j.nanoen.2022.10787210.1016/j.nanoen.2022.107872 ↗
61. 10.1002/adma.20220265910.1002/adma.202202659 ↗
62. 10.1002/aenm.20220016510.1002/aenm.202200165 ↗
63. 10.1002/aenm.20200317110.1002/aenm.202003171 ↗
64. 10.1002/adma.20180827910.1002/adma.201808279 ↗
65. 10.1002/adfm.20210079110.1002/adfm.202100791 ↗
66. 10.1002/adfm.20230020210.1002/adfm.202300202 ↗
67. 10.1002/adma.20180827910.1002/adma.201808279 ↗
68. 10.1002/cjoc.20220066210.1002/cjoc.202200662 ↗
69. 10.1002/adma.20230190610.1002/adma.202301906 ↗
70. 10.1002/adfm.20210276410.1002/adfm.202102764 ↗
71. 10.1038/s41467-022-30127-810.1038/s41467-022-30127-8 ↗
72. 10.1038/s41560-022-01138-y10.1038/s41560-022-01138-y ↗
73. 10.1021/jacs.0c0489010.1021/jacs.0c04890 ↗