journal article·2022-07

Truxenone Triimide: Two‐Dimensional Molecular Arrangements of Triangular Molecules for Air Stable n‐Type Semiconductors

Sharvan Kumar, Yun Hee Koo, Tomohiro Higashino, Wakana Matsuda, Samrat Ghosh, Yusuke Tsutsui, Masayuki Suda, Hiroshi Imahori, Katsuaki Suzuki, Hironori Kaji, Shu Seki

Advanced Electronic Materials· Volume 8· Issue 7
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Abstract

Abstract The preparation of a new class of electron deficient organic compounds is of great interest for the development of high‐performance n‐type organic semiconductors. Herein, the facile synthetic protocol for the isolation of the first examples of truxenone triimide (TTI) is reported. The electrochemical analysis of the resulting TTIs confirms that the multi‐imidization helps in lowering the LUMO energy level, tailoring prerequisite optoelectronic and/or semiconducting properties. Their microscopic charge carrier transport properties and dynamics are screened by flash‐photolysis time‐resolved microwave conductivity measurements. Compound 2D exhibited an electron mobility of 0.27 cm2 V−1 s−1 under ambient conditions.
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Research context

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

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

Affiliations

Department of Molecular Engineering Graduate School of Engineering Kyoto University Nishikyo‐ku Kyoto 615–8510 Japan

Inorganic and Physical Chemistry Laboratory CSIR‐Central Leather Research Institute Adyar Chennai 600 020 India

Institute for Integrated Cell‐Material Sciences (WPI‐iCeMS) Kyoto University Sakyo‐ku Kyoto 606‐8501 Japan

Institute for Chemical Research Kyoto University Uji Kyoto 611–0011 Japan

Funding

Japan Society for the Promotion of Science

References (67)

Show source-provided references
1. 10.1021/cr100380z10.1021/cr100380z ↗
2. 10.1002/adma.20090362810.1002/adma.200903628 ↗
3. 10.1021/cr050156n10.1021/cr050156n ↗
4. 10.1002/adom.20180051210.1002/adom.201800512 ↗
5. 10.1038/nature1168710.1038/nature11687 ↗
6. 10.1038/natrevmats.2018.310.1038/natrevmats.2018.3 ↗
7. 10.1021/acs.chemrev.7b0053510.1021/acs.chemrev.7b00535 ↗
8. 10.1021/acs.accounts.5b0019910.1021/acs.accounts.5b00199 ↗
9. 10.1038/nchem.65710.1038/nchem.657 ↗
10. 10.1039/B614208G10.1039/B614208G ↗
11. 10.1021/ja412290r10.1021/ja412290r ↗
12. 10.1021/acs.accounts.8b0022310.1021/acs.accounts.8b00223 ↗
13. 10.1038/nchem.72310.1038/nchem.723 ↗
14. 10.1021/ja066574710.1021/ja0665747 ↗
15. 10.1021/ja504903j10.1021/ja504903j ↗
16. 10.1039/C8GC01614C10.1039/C8GC01614C ↗
17. 10.1002/anie.20180783610.1002/anie.201807836 ↗
18. 10.1002/chem.20180597810.1002/chem.201805978 ↗
19. 10.1039/C9SC00962K10.1039/C9SC00962K ↗
20. 10.1021/ar200006r10.1021/ar200006r ↗
21. 10.1002/(SICI)1521-4095(200002)12:3<227::AID-ADMA227>3.0.CO;2-U10.1002/(SICI)1521-4095(200002)12:3<227::AID-ADMA227>3.0.CO;2-U ↗
22. 10.1021/cm049391x10.1021/cm049391x ↗
23. 10.1021/ja809555c10.1021/ja809555c ↗
24. 10.1021/ja805746h10.1021/ja805746h ↗
25. 10.1021/acs.chemrev.6b0016010.1021/acs.chemrev.6b00160 ↗
26. 10.1021/ja075242e10.1021/ja075242e ↗
27. 10.1021/ja901077a10.1021/ja901077a ↗
28. 10.1002/anie.20120760810.1002/anie.201207608 ↗
29. 10.1021/jacs.8b1120110.1021/jacs.8b11201 ↗
30. 10.1002/anie.20140244410.1002/anie.201402444 ↗
31. 10.1021/ja807803j10.1021/ja807803j ↗
32. 10.1002/chem.20060141610.1002/chem.200601416 ↗
33. 10.1021/ja016043c10.1021/ja016043c ↗
34. 10.1021/ol901041n10.1021/ol901041n ↗
35. 10.1039/c2sc20241g10.1039/c2sc20241g ↗
36. 10.1021/acs.orglett.9b0113010.1021/acs.orglett.9b01130 ↗
37. 10.1002/(SICI)1521-3773(19980216)37:3<248::AID-ANIE248>3.0.CO;2-510.1002/(SICI)1521-3773(19980216)37:3<248::AID-ANIE248>3.0.CO;2-5 ↗
38. 10.3390/ma305321810.3390/ma3053218 ↗
39. 10.1021/ja011969610.1021/ja0119696 ↗
40. 10.1002/anie.20060420310.1002/anie.200604203 ↗
41. 10.1021/cm502574d10.1021/cm502574d ↗
42. 10.1038/371141a010.1038/371141a0 ↗
43. 10.1002/anie.20200138310.1002/anie.202001383 ↗
44. 10.1021/cr400088w10.1021/cr400088w ↗
45. 10.1021/jacs.5b0280810.1021/jacs.5b02808 ↗
46. 10.1021/jacs.7b0146010.1021/jacs.7b01460 ↗
47. 10.1021/ja805997v10.1021/ja805997v ↗
48. Gabriel S. · Ber. ‐ Dtsch., Chem. Ges. A · 1877 · 10 · 1557
49. 10.1021/cm060188710.1021/cm0601887 ↗
50. 10.1039/C4TA01653J10.1039/C4TA01653J ↗
51. 10.1002/chem.20170576010.1002/chem.201705760 ↗
52. 10.1016/S0040-4039(99)01807-910.1016/S0040-4039(99)01807-9 ↗
53. Krief P. · Synthesis · 2004 · 15 · 2509
54. 10.1039/C8QO00256H10.1039/C8QO00256H ↗
55. 10.1080/0026897630010074110.1080/00268976300100741 ↗
56. 10.1021/ja403624a10.1021/ja403624a ↗
57. CCDC 2083479 (2b) and CCDC 2083480 (2c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
58. 10.1039/C4CP00473F10.1039/C4CP00473F ↗
59. 10.1002/adma.20070246310.1002/adma.200702463 ↗
60. 10.1021/jp803925210.1021/jp8039252 ↗
61. 10.1002/adma.20090260110.1002/adma.200902601 ↗
62. 10.1021/ar200283b10.1021/ar200283b ↗
63. 10.1246/cl.2013.1910.1246/cl.2013.19 ↗
64. 10.1088/0034-4885/29/1/30610.1088/0034-4885/29/1/306 ↗
65. 10.1063/1.150176410.1063/1.1501764 ↗
66. 10.1006/jmra.1996.019710.1006/jmra.1996.0197 ↗
67. 10.1006/jmre.2001.233610.1006/jmre.2001.2336 ↗