journal article·2023-01-11

n-Type Polymer Semiconductors Based on Dithienylpyrazinediimide

Suxiang Ma, Junwei Wang, Kui Feng, Hao Zhang, Ziang Wu, Yimei Wang, Bin Liu, Yongchun Li, Mingwei An, Raúl Gonzalez-Nuñez, Rocío Ponce Ortiz, Han Young Woo, Xugang Guo

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Abstract

The development of n-type organic semiconductors critically relies on the design and synthesis of highly electron-deficient building blocks with good solubility and small steric hindrance. We report here a strongly electron-deficient dithienylpyrazinediimide (TPDI) and its n-type semiconducting polymers. The pyrazine substitution leads to the resulting polymers with much lower-lying lowest unoccupied molecular orbital (LUMO) levels and improved backbone planarity compared to the reported dithienylbenzodiimide (TBDI)- and fluorinated dithienylbenzodiimide (TFBDI)-based polymer analogues, thus yielding n-type transport character with an electron mobility up to 0.44 cm2 V–1 s–1 in organic thin-film transistors. These results demonstrate that dithienylpyrazinediimide is a highly promising electron-deficient building block for constructing high-performance n-type polymers and the incorporation of pyrazine into imide-functionalized (hetero)arenes is an effective strategy to develop n-type polymers with deep-lying frontier molecular orbital (FMO) levels for organic optoelectronic devices.
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Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Organic Light-Emitting Diodes Research

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

Affiliations

Department of Materials Science and Engineering, Southern University of Science and Technology (SUSTech), Shenzhen 518055, Guangdong, China

Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology (SUSTech), Shenzhen 518055, Guangdong, China

Department of Chemistry, Southern University of Science and Technology (SUSTech), Shenzhen 518055, Guangdong, China

Department of Chemistry, Korea University, Seoul 136-713, South Korea

Department of Physical Chemistry, Faculty of Sciences, University of Málaga, Málaga 29071, Spain

Funding

Junta de Andaluc??a · National Research Foundation of Korea · China Postdoctoral Science Foundation · Southern University of Science and Technology · National Natural Science Foundation of China · The Ministry of Science and Innovation (Spain) · Guangdong Basic and Applied Basic Research Foundation · Shenzhen Basic Research Fund

References (68)

Show source-provided references
1. 10.1021/cr500225d10.1021/cr500225d ↗
2. 10.1016/j.chempr.2018.08.00510.1016/j.chempr.2018.08.005 ↗
3. 10.1039/c3ee00015j10.1039/c3ee00015j ↗
4. 10.1039/D2TC00684G10.1039/D2TC00684G ↗
5. 10.1021/ja802266u10.1021/ja802266u ↗
6. 10.1038/s41586-021-03942-010.1038/s41586-021-03942-0 ↗
7. 10.1002/chem.20220022210.1002/chem.202200222 ↗
8. Huang F. · Acta Polym. Sin. · 2019 · 50 · 988
9. 10.1038/s41560-018-0181-510.1038/s41560-018-0181-5 ↗
10. 10.1016/j.enchem.2020.10004210.1016/j.enchem.2020.100042 ↗
11. 10.1021/acs.chemmater.2c0092910.1021/acs.chemmater.2c00929 ↗
12. 10.1021/acsami.1c0244210.1021/acsami.1c02442 ↗
13. 10.1002/adfm.20210850810.1002/adfm.202108508 ↗
14. 10.1021/acsami.0c1835110.1021/acsami.0c18351 ↗
15. 10.1007/s11426-022-1247-110.1007/s11426-022-1247-1 ↗
16. 10.1002/agt2.28110.1002/agt2.281 ↗
17. 10.1002/adfm.20090180310.1002/adfm.200901803 ↗
18. 10.1039/D1TC00079A10.1039/D1TC00079A ↗
19. 10.1002/adma.20210432510.1002/adma.202104325 ↗
20. 10.1016/j.chempr.2020.05.01210.1016/j.chempr.2020.05.012 ↗
21. 10.1021/ar200006r10.1021/ar200006r ↗
22. 10.1039/C7TC01680H10.1039/C7TC01680H ↗
23. 10.1002/adma.20160054110.1002/adma.201600541 ↗
24. 10.1021/acs.accounts.1c0038110.1021/acs.accounts.1c00381 ↗
25. 10.1002/chem.20180360510.1002/chem.201803605 ↗
26. Shi Y. · Acta Polym. Sin. · 2019 · 50 · 873
27. 10.1039/C1JM14713G10.1039/C1JM14713G ↗
28. 10.1021/acs.macromol.9b0117310.1021/acs.macromol.9b01173 ↗
29. 10.1021/acs.macromol.0c0202110.1021/acs.macromol.0c02021 ↗
30. 10.1002/adma.20170030910.1002/adma.201700309 ↗
31. 10.1021/ol801918y10.1021/ol801918y ↗
32. 10.1016/j.progpolymsci.2013.08.00710.1016/j.progpolymsci.2013.08.007 ↗
33. 10.1021/ma200906310.1021/ma2009063 ↗
34. 10.1002/anie.20160430710.1002/anie.201604307 ↗
35. 10.1002/anie.20110641110.1002/anie.201106411 ↗
36. 10.1021/ja107678m10.1021/ja107678m ↗
37. 10.1021/jacs.8b0214410.1021/jacs.8b02144 ↗
38. 10.1002/ange.20170842110.1002/ange.201708421 ↗
39. 10.1002/ange.20210928110.1002/ange.202109281 ↗
40. 10.1002/adma.20220134010.1002/adma.202201340 ↗
41. 10.1002/adfm.20211195010.1002/adfm.202111950 ↗
42. 10.1002/adma.20160137310.1002/adma.201601373 ↗
43. 10.1039/C7TC02903A10.1039/C7TC02903A ↗
44. 10.1002/adma.20180722010.1002/adma.201807220 ↗
45. 10.1002/solr.20180026510.1002/solr.201800265 ↗
46. 10.1021/acsami.9b1313810.1021/acsami.9b13138 ↗
47. 10.1021/acs.chemmater.0c0397510.1021/acs.chemmater.0c03975 ↗
48. 10.1002/ange.20120406610.1002/ange.201204066 ↗
49. 10.1021/jacs.7b0403110.1021/jacs.7b04031 ↗
50. 10.1002/adfm.20180187410.1002/adfm.201801874 ↗
51. 10.1021/acs.orglett.5b0230610.1021/acs.orglett.5b02306 ↗
52. 10.1039/C2CC37266E10.1039/C2CC37266E ↗
53. 10.1039/c3cc40811f10.1039/c3cc40811f ↗
54. 10.1021/jacs.9b1010710.1021/jacs.9b10107 ↗
55. 10.1002/adma.20100432510.1002/adma.201004325 ↗
56. 10.1021/ja407471b10.1021/ja407471b ↗
57. 10.1021/ja991683p10.1021/ja991683p ↗
58. 10.1002/ange.20200229210.1002/ange.202002292 ↗
59. 10.1021/acs.accounts.1c0044310.1021/acs.accounts.1c00443 ↗
60. 10.1002/ange.20190583510.1002/ange.201905835 ↗
61. 10.1021/acs.chemmater.8b0367010.1021/acs.chemmater.8b03670 ↗
62. 10.1021/acs.macromol.8b0083910.1021/acs.macromol.8b00839 ↗
63. 10.1021/jacs.0c0708310.1021/jacs.0c07083 ↗
64. 10.1038/ncomms1090810.1038/ncomms10908 ↗
65. 10.1021/acs.chemmater.1c0443210.1021/acs.chemmater.1c04432 ↗
66. 10.1021/jp405064410.1021/jp4050644 ↗
67. 10.1021/jacs.0c1160810.1021/jacs.0c11608 ↗
68. 10.1021/ja01613a06610.1021/ja01613a066 ↗