Citation: Zhilei Zhang, Yanan Sun, Xiaosong Shi, Xiaozhe Yin, Dawei Liu, Erjing Wang, Jie Liu, Yuanyuan Hu, Lang Jiang. Molecular tailoring towards two-dimensional organic crystals at the thickness limit[J]. Chinese Chemical Letters, ;2025, 36(9): 110786. doi: 10.1016/j.cclet.2024.110786 shu

Molecular tailoring towards two-dimensional organic crystals at the thickness limit

Zhilei Zhang ^{a, b} ,
Yanan Sun ^{a, b} ,
Xiaosong Shi ^{a, b} ,
Xiaozhe Yin ^{a, b} ,
Dawei Liu ^{a, b} ,
Erjing Wang ^c ,
Jie Liu ^{a, *,} ,
Yuanyuan Hu ^d ,
Lang Jiang ^{a, *,}

a.
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of the Chinese Academy of Sciences, Beijing 100049, China
c.
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry-of-Education Key Laboratory for the Green Preparation and Application of Functional Materials, Faculty of Materials Science and Engineering, Hubei University, Wuhan 430062, China
d.
Key Laboratory for Micro/Nano Optoelectronic Devices of Ministry of Education & International Science and Technology Innovation Cooperation Base for Advanced Display Technologies of Hunan Province, School of Physics and Electronics, Hunan University, Changsha 410082, China

liujie2009@iccas.ac.cn

ljiang@iccas.ac.cn

Received Date: 10 October 2024
Revised Date: 6 December 2024
Accepted Date: 19 December 2024
Available Online: 20 December 2024

Figures(6)

Advances in controllable growth of ultrathin two-dimensional molecular crystals (2DMCs) or even monolayer molecular crystals (MMCs) propelled their application in high-performance, high-sensitivity, low-contact-resistance optoelectronic devices. However, the rational molecular design strategies for materials prone to grow into ultrathin 2DMC or MMC have rarely been addressed. Here, systematically tailoring the π-conjugation and alkyl chain types of asymmetric anthracene derivatives, 2DMCs and even MMCs were obtained under the synergetic regulation of inter- and intralayer interactions. High-quality MMCs were obtained for SAP-C6 by traditional physical vapor transport technique (PVT), and corresponding organic field-effect transistors (OFETs) exhibited high mobility of 3.22 cm² V^-1 s^-1. In addition, band-like charge transport with low activation energy was achieved by SAP-C6 MMC-OFETs. Furthermore, the SAP-C6 MMC-based device exhibits excellent thermal stability, retaining ~70% of its initial performance at 140 ℃ in air, which is the first report on the thermal stability of MMC devices. This research highlights the potential of alkyl-substituted asymmetric molecules as a design strategy to achieve ultrathin 2DMC or MMC growth, and improve the mobility and thermal stability in OFETs.
- Asymmetric anthracene derivatives,
- Monolayer molecular crystals (MMCs),
- Field-effect transistors,
- Thermal stability,
- Contact resistance
1. [1]
  A. Yamamura, S. Watanabe, M. Uno, M. Mitani, et al., Sci. Adv. 4 (2018) eaao5758.
2. [2]
  B. Crone, A. Dodabalapur, Y.Y. Lin, et al., Nature 403 (2000) 521–523.
3. [3]
  Q. Wang, J. Qian, Y. Li, et al., Adv. Funct. Mater. 26 (2016) 3191–3198. doi: 10.1002/adfm.201600304
4. [4]
  Y. Shi, L. Jiang, J. Liu, et al., Nat. Commun. 9 (2018) 2933.
5. [5]
  M. Xiao, J. Liu, C. Liu, et al., Nat. Commun. 12 (2021) 2774.
6. [6]
  Y. Wang, L. Sun, C. Wang, F. et al., Chem. Soc. Rev. 48 (2019) 1492–1530. doi: 10.1039/c8cs00406d
7. [7]
  X. Zhang, X. Zhao, L. Rao, et al., Nano Res. 15 (2021) 858–863.
8. [8]
  Z. Luo, B. Peng, J. Zeng, et al., Nat. Commun. 12 (2021) 1928. doi: 10.37188/cjl.20210304
9. [9]
  Y. Guo, K. Li, D. Zou, et al., Adv. Electron. Mater. 10 (2023) 2300570.
10. [10]
  H. Chen, S. Dong, M. Bai, et al., Adv. Mater. 27 (2015) 2113–2120. doi: 10.1002/adma.201405378
11. [11]
  Y. Fan, J. Liu, W. Hu, et al., J. Mater. Chem. C 8 (2020) 13154–13168. doi: 10.1039/d0tc03193c
12. [12]
  M. Pei, J. Guo, B. Zhang, et al., Adv. Phy. X 5 (2020) 1747945. doi: 10.1080/23746149.2020.1747945
13. [13]
  E.M. Mannebach, J.W. Spalenka, P.S. Johnson, et al., Adv. Funct. Mater. 23 (2013) 554–564. doi: 10.1002/adfm.201201548
14. [14]
  L. Jiang, J. Liu, Y. Shi, et al., J. Mater. Chem. C 7 (2019) 3436–3442. doi: 10.1039/c9tc00443b
15. [15]
  J. Zeng, D. He, J. Qiao, et al., Nat. Commun. 14 (2023) 324.
16. [16]
  B. Peng, K. Cao, A.H.Y. Lau, et al., Adv. Mater. 32 (2020) 2002281.
17. [17]
  H. Li, Y. Shi, G. Han, et al., Angew. Chem. Int. Ed. 59 (2020) 4380–4384. doi: 10.1002/anie.201916397
18. [18]
  Y. Dong, S. Chertopalov, K. Maleski, et al., Adv. Mater. 30 (2018) 1705714.
19. [19]
  Y. Zhang, J. Qiao, S. Gao, et al., Phys. Rev. Lett. 116 (2016) 016602. doi: 10.1103/PhysRevLett.116.016602
20. [20]
  F. Qiu, J. Liu, H. Zhang, et al., Adv. Electron. Mater. 6 (2020) 2000579.
21. [21]
  J. Liu, W. Hu, L. Jiang, Sci. Bull. 68 (2023) 1474–1477.
22. [22]
  J. Liu, L. Jiang, W. Hu, et al., Sci. China Chem. 62 (2019) 313–330.
23. [23]
  D. He, Y. Zhang, Q. Wu, et al., Nat. Commun. 5 (2014) 5162.
24. [24]
  D. He, J. Qiao, L. Zhang, et al., Sci. Adv. 3 (2017) e1701186.
25. [25]
  J. Zhang, J. Guo, H. Zhang, et al., Precis. Chem. 2 (2024) 380–397. doi: 10.1021/prechem.3c00124
26. [26]
  J. Wang, X. Wu, J. Pan, et al., Adv. Mater. 32 (2020) 2003315.
27. [27]
  J. Wang, Z. Ren, J. Pan, et al., Adv. Mater. 35 (2023) 2301017.
28. [28]
  Z. Chen, S. Duan, X. Zhang, et al., Mater. Chem. Front. 8 (2024) 2227–2272. doi: 10.1039/d3qm01281f
29. [29]
  F. Sheng, W. Deng, X. Ren, et al., Adv. Mater. 36 (2024) 2401822.
30. [30]
  X. Zhang, X. Dai, H. Wan, et al., Adv. Funct. Mater. 34 (2024) 2314134.
31. [31]
  W. Hu, J.Y. Yao, Y.Z. Zhang, et al., Angew. Chem. Int. Ed. 58 (2019) 16082–16086.
32. [32]
  J. Liu, Y. Yu, J. Liu, et al., Adv. Mater. 34 (2022) 2107574.
33. [33]
  H. Tian, J. Wang, J. Shi, et al., J. Mater. Chem. 15 (2005) 3026–3033. doi: 10.1039/b504044b
34. [34]
  L. Jiang, H. Dong, Q. Meng, et al., Adv. Mater. 23 (2011) 2059–2063. doi: 10.1002/adma.201004551
35. [35]
  X. Zhu, Y. Zhang, X. Ren, et al., Small. 15 (2019) 1902187.
36. [36]
  S. Inoue, T. Higashino, S. Arai, et al., Chem. Sci. 11 (2020) 12493–12505. doi: 10.1039/d0sc04461j
37. [37]
  Y. Dong, Y. Sun, J. Liu, et al., Adv. Sci. 9 (2022) 2106085.
38. [38]
  H. Iino, T. Usui, J. Hanna, Nat. Commun. 6 (2015) 6828.
39. [39]
  G. Schweicher, V. Lemaur, C. Niebel, et al., Adv. Mater. 27 (2015) 3066–3072. doi: 10.1002/adma.201500322
40. [40]
  J. Li, Z. Qin, Y. Sun, et al., Angew. Chem. Int. Ed. 134 (2022) e202206825.
41. [41]
  K. He, W. Li, H. Tian, et al., ACS Appl. Mater. Interfaces 9 (2017) 35427–35436. doi: 10.1021/acsami.7b10675
42. [42]
  J.Y. Back, T.K. An, Y.R. Cheon, et al., ACS Appl. Mater. Interfaces 7 (2015) 351–358. doi: 10.1021/am5063103
43. [43]
  F. Qiu, Y. Dong, J. Liu, et al., J. Mater. Chem. C 8 (2020) 6006–6012. doi: 10.1039/d0tc01122c
44. [44]
  X. Shi, Y. Sun, J. Liu, et al., J. Mater. Chem. C 11 (2023) 11822–11827. doi: 10.1039/d3tc02533k
45. [45]
  M. Chen, L. Yan, Y. Zhao, et al., J. Mater. Chem. C 6 (2018) 7416–7444. doi: 10.1039/c8tc01865k
46. [46]
  X. Zhang, G. Zhao, Y. Zhen, et al., J. Mater. Chem. C 3 (2015) 5368–5371.
47. [47]
  M. Chen, Y. Zhao, L. Yan, et al., Angew. Chem. Int. Ed. 56 (2017) 722–727. doi: 10.1002/anie.201608131
48. [48]
  J. Liu, H. Zhang, H. Dong, et al., Nat. Commun. 6 (2015) 10032.
49. [49]
  Y. Dong, Y. Guo, H. Zhang, et al., Front. Chem. 7 (2019) 11.
50. [50]
  R. Li, X. Zhang, H. Dong, et al., Adv. Mater. 28 (2016) 1697–1702. doi: 10.1002/adma.201504370
51. [51]
  L.F. Drummy, P.K. Miska, D. Alberts, et al., J. Phy. Chem. B 110 (2006) 6066–6071. doi: 10.1021/jp054951g
52. [52]
  Q. Tang, L. Jiang, Y. Tong, et al., Adv. Mater. 20 (2008) 2947–2951. doi: 10.1002/adma.200800669
53. [53]
  Y. Sun, X. Shi, Y. Yu, et al., Adv. Sci. 11 (2024) 2400112.
54. [54]
  J. Zhang, X. Lu, Y. Sun, et al., ACS Mater. Lett. 4 (2022) 548–553. doi: 10.1021/acsmaterialslett.1c00844
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