Citation: Zhengjie Miao, Chuanqiang Zhou, Yuanyuan Ren, Xiangping Xu, Ju Xie, Jie Han. Hierarchical chiral nanoribbons of achiral oligoaniline: temperature induced helicity inversion and enantioselective crystallization application[J]. Acta Physico-Chimica Sinica, ;2026, 42(10): 100256. doi: 10.1016/j.actphy.2026.100256 shu

Hierarchical chiral nanoribbons of achiral oligoaniline: temperature induced helicity inversion and enantioselective crystallization application

Zhengjie Miao ¹ ,
Chuanqiang Zhou ^1,2,, ,
Yuanyuan Ren ¹ ,
Xiangping Xu ¹ ,
Ju Xie ¹ ,
Jie Han ^1,,

1.
Jiangsu Provincial Key Laboratory of Green & Functional Materials and Environmental Chemistry, College of Chemistry and Materials, Yangzhou University, Yangzhou 225002, Jiangsu Province, China;
2.
Testing Center, Yangzhou University, Yangzhou 225002, Jiangsu Province, China

Corresponding author: Chuanqiang Zhou, Jie Han,
Received Date: 13 December 2025
Revised Date: 5 February 2026
Accepted Date: 9 February 2026

Hierarchical chiral nanostructures with controllable chirality are highly desirable due to their novel chirality-related applications. They predominantly rely on chiral molecules; however, the intrinsic chirality interference problem for applications such as chiral separation cannot be ignored. Herein, we report the synthesis of hierarchical chiral nanoribbons from achiral oligoanilines through a facile but effective route, where the oxidation of aniline in achiral system leads to the formation helically twisted nanoribbons through a hierarchical self-assembly process involving intermediate nanowires. Remarkably, both the torsion direction and supramolecular chirality can be modulated and even reversed by simply adjusting the reaction temperature. Mechanistic investigations revealed that achiral oligoaniline of triphenylamine derivative was generated during the oxidation process, where the asymmetrical self-assembly was modulated by intermolecular interactions with temperature. The resulting hierarchical chiral nanoribbons were successfully employed to induce enantioselective crystallization of amino acids from racemic mixtures, enabling effective chiral resolution without the introduction of any extrinsic chiral species. This work presents a feasible strategy for achieving hierarchical chiral nanostructures in an achiral system and showcases its practical application in chiral separation using exclusively achiral materials.
- Supramolecular chirality,
- Hierarchical helices,
- Achiral fabrication,
- Oligoaniline,
- Enantioselective crystallization
1. [1]
  D.G. Blackmond, Cold Spring Harb. Perspect. Biol. 11(3) (2019) a032540, https://doi.org/10.1101/cshperspect.a032540.
2. [2]
  D.R. Link, G. Natale, R. Shao, J.E. Maciennan, N. A. Clark, E. a Körblova, D.M.Walba, Science 278(5345) (1997) 1924, https://doi.org/10.1126/science.278.5345.1924.
3. [3]
  G. Singh, H. Chan, A. Baskin, E. Gelman, N. Repnin, P. Král, R. Klajn, Science 345(2014) 1149, https://doi.org/10.1126/science.1254132.
4. [4]
  Y. Li, G. J. Stec, H. K. Kim, S. Thapa, S.-L. Zheng, A. McClelland, J. A. Mason, Nat. Chem. 17(2025) 169, https://doi.org/10.1038/s41557-024-01696-6.
5. [5]
  J. Mun, M. Kim, Y. Yang, T. Badloe, J. Ni, Y. Chen, C. Qiu, J. Rho, Light. Sci. Appl. 9(2020) 139, https://doi.org/10.1038/s41377-020-00367-8.
6. [6]
  R. Naaman, Y. Paltiel, D. H. Waldeck, Nat. Rev. Chem 3(2019) 250, https://doi.org/10.1038/s41570-019-0087-1.
7. [7]
  N. Micali, H. Engelkamp, P.G. van Rhee, P. C. M. Christianen, L. M. Scolaro, J. C. Maan, Nat. Chem 4(2012) 201, https://doi.org/10.1038/nchem.1264.
8. [8]
  K. Fu, Y. Zhao, G. Liu, Nat. Commun. 15(2024) 9571, https://doi.org/10.1038/s41467-024-53928-5.
9. [9]
  Y. Bi, Z. Wang, T. Liu, D. Sun, N. Godbert, H. Li, J. Hao, X. Xin, ACS Nano 15(10) (2021) 15910, https://doi.org/10.1021/acsnano.1c03824.
10. [10]
  J. Shen, J. Fu, P. Mahato, M. Wang, B. Liu, Z. Yang, W. Qi, D. Sun, X. Xin, ACS Nano 19(35) (2025) 31516, https://doi.org/10.1021/acsnano.5c08207.
11. [11]
  W. Wang, T. Liu, T. Zhao, D. Sun, H. Li, P. Xing, X. Xin, Adv. Sci. 11(1) (2023) 2305102, https://doi.org/10.1002/advs.202305102.
12. [12]
  N. Feng, Z. Wang, D. Sun, L. Zhang, X. Xin, P. Sun, M. Azam, H. Li, Small 20(6) (2023) 2305366, https://doi.org/10.1002/smll.202305366.
13. [13]
  N. Feng, Z. Wang, D. Sun, P. Sun, X. Xin, X. Cheng, H. Li, Adv. Optical Mater. 20(15) (2022) 2102319, https://doi.org/10.1002/adom.202102319.
14. [14]
  K.S. Park, Z. Xue, B.B. Patel, H. An, J.J. Kwok, P. Kafle, Q. Chen, D. Shukla, Y. Diao, Nat. Commun. 13(2022) 2738, https://doi.org/10.1038/s41467-022-30420-6.
15. [15]
  J. Karcz, J. Herman, N. Rychłowicz, P. Kula, E. Górecka, J. Szydlowska, P. W. Majewski, D. Pociecha, Science 384(2024) 1096, https://doi.org/10.1126/science.adn6812.
16. [16]
  T.J. Ugras, R.B. Carson, R.P. Lynch, H. Li, Y. Yao, L. Cupellini, K. A. Page, D. Wang, A. Arbe, S. Bals, et al., Science 387(6733) (2025), https://doi.org/10.1126/science.ado7201.
17. [17]
  G.F. Liu, L. Y. Zhu, W. Ji, C. L. Feng, Z. X. Wei, Angew. Chem. Int. Ed. 128(7) (2015) 2457, https://doi.org/10.1002/ange.201510140.
18. [18]
  C. Du, Z. Li, X. Zhu, G. Ouyang, M. Liu, Nat. Nanotechnol. 17(12) (2022) 1294, https://doi.org/10.1038/s41565-022-01234-w.
19. [19]
  M. Kim, M. Zhang, Y. Zhu, Y. Yan, X. Pu, W. Choi, S. Chung, K. Cho, J. Kim, V. Tsukruk, et al., Science 389(6761) (2025) eadu0296, https://doi.org/10.1126/science.adu0296.
20. [20]
  C. Kulkarni, P.A. Korevaar, K.K. Bejagam, A.R.A. Palmans, E.W. Meijer, S.J. George, J. Am. Chem. Soc. 139(39) (2017) 13867, https://doi.org/10.1021/jacs.7b07639.
21. [21]
  H. Jiang, Y. Jiang, J. Han, L. Zhang, M. Liu, Angew. Chem. Int. Ed. 58(3) (2018) 789, https://doi.org/10.1002/anie.201811060.
22. [22]
  G. Liu, J. Sheng, W.L. Teo, G. Yang, H. Wu, Y. Li, Y. Zhao, J. Am. Chem. Soc. 140(47) (2018) 16278, https://doi.org/10.1021/jacs.8b10024.
23. [23]
  C. Zhou, Y. Ren, J. Han, X. Gong, Z. Wei, J. Xie, R. Guo, J. Am. Chem. Soc. 140(30) (2018) 9417, https://doi.org/10.1021/jacs.7b12178.
24. [24]
  C. Zhou, Y. Ren, J. Han, Q. Xu, R. Guo, ACS Nano 13(3) (2019) 3534, https://doi.org/10.1021/acsnano.8b09784.
25. [25]
  C. Chen, B. Zhao, J. Deng, ACS Macro Lett. 4(4) (2015) 348, https://doi.org/10.1021/acsmacrolett.5b00088.
26. [26]
  B. Zhao, J. Lin, J. Deng, D. Liu, Macromol. Rapid. Comm. 39(2018) 1800072, https://doi.org/10.1002/marc.201800072.
27. [27]
  L. Zhang, P. Fu, B. Wang, M. Liu, Q. Zhao, X. Pang, Z. Cui, React. Funct. Polym. 131(2018) 326, https://doi.org/10.1016/j.reactfunctpolym.2018.08.004.
28. [28]
  P. Liu, H. Zhang, B. Zhou, T. Cao, W. Chen, Y. Li, J. Hao, R. Pan, J. Cheng, J.Sci. Sin. Chim. 54(8) (2024) 1337, https://doi.org/10.1360/ssc-2024-0073.
29. [29]
  J. Stejskal, I. Sapurina, M. Trchová, Prog. Polym. Sci. 35(12) (2010) 1420, https://doi.org/10.1016/j.progpolymsci.2010.07.006.
30. [30]
  X. Wei, Y. Wang, J. Li, F. Wang, G. Chang, T. Fu, W. Zhou, Carbohyd. Polym. 201(2018) 387, https://doi.org/10.1016/j.carbpol.2018.08.031.
31. [31]
  D. Xiang, K. Li, K. Miao, R. Long, Y. Xiong, X. Kang, Acta Phys.-Chim. Sin. 40(8) (2024) 2308027, https://doi.org/10.3866/pku.Whxb202308027.
32. [32]
  H. Ishikawa, N. Uemura, R. Saito, Y. Yoshida, T. Mino, Y. Kasashima, M. Sakamoto, Chem.-Eur. J. 25(41) (2019) 9758, https://doi.org/10.1002/chem.201901889.
33. [33]
  F. Zhou, O. Shemchuk, M.D. Charpentier, C. Matheys, L. Collard, J. H. ter Horst, T. Leyssens, Angew. Chem. Int. Ed. 60(37) (2021) 20264, https://doi.org/10.1002/anie.202107804.
34. [34]
  X. Yan, J. Cao, H. Luo, Z. Li, Z. Cao, Y. Mo, Y.-B. Jiang, Nat. Commun. 15(1) (2024), https://doi.org/10.1038/s41467-024-53744-x.
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