Citation: Changhui Yu, Peng Shang, Huihui Hu, Yuening Zhang, Xujin Qin, Linyu Han, Caihe Liu, Xiaohan Liu, Minghua Liu, Yuan Guo, Zhen Zhang. Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy[J]. Chinese Chemical Letters, ;2024, 35(10): 109805. doi: 10.1016/j.cclet.2024.109805 shu

Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy

Changhui Yu ^{a, b} ,
Peng Shang ^{a, b} ,
Huihui Hu ^{a, b} ,
Yuening Zhang ^{a, b} ,
Xujin Qin ^{a, b} ,
Linyu Han ^{a, b} ,
Caihe Liu ^{a, b} ,
Xiaohan Liu ^{a, b} ,
Minghua Liu ^c ,
Yuan Guo ^{a, b} ,
Zhen Zhang ^{a, b, *,}

a.
Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Molecular Reaction Dynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Beijing National Laboratory for Molecular Science, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

zhangz@iccas.ac.cn

Received Date: 24 February 2024
Revised Date: 20 March 2024
Accepted Date: 20 March 2024
Available Online: 21 March 2024

Figures(4)

Directed self-assembly has been used to create micro-nano scale patterns, including chiral periodic structures of organic molecules, for potential applications in optics, photonics, metamaterials, and medical and sensing technologies. This study presents a straightforward approach for fabricating large-scale chiral grating porphyrin assemblies through template-assisted techniques. The solution of tetrakis(4-sulfonatophenyl)porphyrin (TPPS) was induced by chiral amino acids (L/D-arginine and L/D-serine) to self-assemble into highly ordered chiral grating structures with the assistance of sodium dodecyl sulfate (SDS). The structures show precise line widths (5.5 µm) and gaps (18 µm). Using in situ optical microscopy and second harmonic generation (SHG) microscopy, the chiral characteristics and dynamic evolution of the template-assisted self-assembly are investigated. It is found that the chirality of amino acids induced TPPS self-assembled into chiral structures and the liquid contraction interface significantly enhanced the chirality of the assemblies. This study is significant for understanding the mechanism of chiral evolution and designing novel micro-nano materials with predetermined chiral properties.
- Second harmonic generation microscopy,
- Chiral assembly,
- Porphyrin,
- Chiral evolution,
- Template-assisted self-assembly,
- Micro-nano structure
1. [1]
  B. Jeong, H. Han, C. Park, Adv. Mater. 32 (2020) 2000597. doi: 10.1002/adma.202000597
2. [2]
  Z. Qu, P. Zhou, F. Min, et al., Sci. Adv. 9 (2023) eadf3567. doi: 10.1126/sciadv.adf3567
3. [3]
  T.W. Park, Y.L. Kang, E.B. Kang, et al., Sci. Adv. 10 (2023) 2303412. doi: 10.1002/advs.202303412
4. [4]
  M. Su, F.F. Qin, Z.Y. Zhang, et al., Angew. Chem. Int. Ed. 59 (2020) 14234–14240. doi: 10.1002/anie.202007224
5. [5]
  E. Yashima, N. Ousaka, D. Taura, et al., Chem. Rev. 116 (2016) 13752–13990. doi: 10.1021/acs.chemrev.6b00354
6. [6]
  W. Wang, Z. Wang, D. Sun, et al., Nanomaterials 12 (2022) 424. doi: 10.3390/nano12030424
7. [7]
  S. Huang, H.F. Yu, Q. Li, Adv. Sci. 8 (2021) 2002132. doi: 10.1002/advs.202002132
8. [8]
  A. Dhamija, B. Saha, D. Chandel, et al., Inorg. Chem. 59 (2020) 801–809. doi: 10.1021/acs.inorgchem.9b03062
9. [9]
  X. Zhang, J. Jie, W. Deng, et al., Adv. Mater. 28 (2016) 2475–2503. doi: 10.1002/adma.201504206
10. [10]
  X. Li, L. Chen, Y. Ma, et al., Adv. Funct. Mater. 32 (2022) 2205462. doi: 10.1002/adfm.202205462
11. [11]
  B. Shen, Y. Kim, M. Lee, et al., Adv. Mater. 32 (2020) 1905669. doi: 10.1002/adma.201905669
12. [12]
  A. Kim, K.S. Jang, J. Kim, et al., Adv. Mater. 25 (2013) 6219–6225. doi: 10.1002/adma.201302719
13. [13]
  J.M. Lim, Z.S. Yoon, J.Y. Shin, et al., Chem. Commun. (2009) 261–273.
14. [14]
  L. Zhang, T. Wang, J. Jiang, et al., Aggregate 4 (2022) e198.
15. [15]
  M. Imran, M. Ramzan, A.K. Qureshi, et al., Biosensors 8 (2018) 95. doi: 10.3390/bios8040095
16. [16]
  H. Hu, H. Wang, Y. Yang, et al., Angew. Chem. Int. Ed. 61 (2022) e202200799. doi: 10.1002/anie.202200799
17. [17]
  Y. Zhang, C. Xu, B. Li, RSC Adv. 3 (2013) 6044. doi: 10.1039/c3ra22525a
18. [18]
  H.S. Peng, Y.F. Lu, Adv. Mater. 20 (2008) 797–800. doi: 10.1002/adma.200701927
19. [19]
  Q.H. Zeng, P.P. Chen, Z.F. Li, et al., ACS Appl. Mater. Interfaces 13 (2021) 48569–48581. doi: 10.1021/acsami.1c12086
20. [20]
  B.B. Beyene, C.H. Hung, Coord. Chem. Rev. 410 (2020) 213234. doi: 10.1016/j.ccr.2020.213234
21. [21]
  T. Liu, Y. Liu, X. Gao, et al., Chin. Chem. Lett. 34 (2023) 107883. doi: 10.1016/j.cclet.2022.107883
22. [22]
  S. Wu, Z.Z. Yin, D. Wu, et al., Langmuir 35 (2019) 16761–16769. doi: 10.1021/acs.langmuir.9b03255
23. [23]
  R. Zagami, M.A. Castriciano, A. Romeo, et al., Int. J. Mol. Sci. 24 (2023) 1695. doi: 10.3390/ijms24021695
24. [24]
  C. Kulkarni, A.K. Mondal, T.K. Das, et al., Adv. Mater. 32 (2020) 1904965. doi: 10.1002/adma.201904965
25. [25]
  S. Wang, H.J. Jiang, L. Zhang, et al., ChemPlusChem 83 (2018) 1038–1043. doi: 10.1002/cplu.201800390
26. [26]
  D. Yang, P.F. Duan, M.H. Liu, Angew. Chem. Int. Ed. 57 (2018) 9357–9361. doi: 10.1002/anie.201804402
27. [27]
  M. Stefanelli, G. Magna, F. Zurlo, et al., ACS Appl. Mater. Interfaces 11 (2019) 12077–12087. doi: 10.1021/acsami.8b22749
28. [28]
  J.D. Byers, H.I. Yee, T. Petrallimallow, et al., Phys. Rev. B 49 (1994) 14643–14647. doi: 10.1103/PhysRevB.49.14643
29. [29]
  G. Albano, A. Taddeucci, G. Pescitelli, et al., Chem. Eur. J. 29 (2023) e202301982. doi: 10.1002/chem.202301982
30. [30]
  P. Yan, A.C. Millard, M. Wei, et al., J. Am. Chem. Soc. 128 (2006) 11030–11031. doi: 10.1021/ja0635534
31. [31]
  V.K. Valev, B.D. Clercq, X. Zheng, et al., Opt. Express 20 (2012) 256–264. doi: 10.1364/OE.20.000256
32. [32]
  T. Verbiest, M. Kauranen, A. Persoons, J. Mater. Chem. 9 (1999) 2005–2012. doi: 10.1039/a902421b
33. [33]
  H. Su, Y. Guo, W. Gao, et al., Sci. Rep. 6 (2016) 22061. doi: 10.1038/srep22061
34. [34]
  M.J. Huttunen, G. Bautista, M. Decker, et al., Opt. Mater. Express 1 (2011) 46–56. doi: 10.1364/OME.1.000046
35. [35]
  H. Lee, M.J. Huttunen, K.J. Hsu, et al., Biomed. Opt. Express 4 (2013) 909–916. doi: 10.1364/BOE.4.000909
36. [36]
  L. Lin, Y. Li, X. Qin, et al., J. Chem. Phys. 156 (2022) 094704. doi: 10.1063/5.0069860
37. [37]
  M. Xue, L. Zhang, M. Liu, et al., J. Phys. Chem. B 124 (2020) 8179–8187. doi: 10.1021/acs.jpcb.0c05545
38. [38]
  K. Claborn, E. Puklin-Faucher, M. Kurimoto, et al., J. Am. Chem. Soc. 125 (2003) 14825–14831. doi: 10.1021/ja035644w
39. [39]
  M. Savoini, P. Biagioni, S.C.J. Meskers, et al., J. Phys. Chem. Lett. 2 (2011) 1359–1362. doi: 10.1021/jz200524m
40. [40]
  Z.H. Guo, J.Z. Li, R.L. Liu, et al., Nano Lett. 23 (2023) 7434–7441. doi: 10.1021/acs.nanolett.3c01863
41. [41]
  L.U. Castaño, K. Mirsanaye, L. Kontenis, et al., J. Biophotonics 16 (2023) e202200284. doi: 10.1002/jbio.202200284
42. [42]
  M.Y. Chen, M.J. Huttunen, C.W. Kan, et al., Opt. Commun. 422 (2018) 56–63. doi: 10.1016/j.optcom.2018.03.005
43. [43]
  E.A. Mamonov, A.I. Maydykovskiy, I.A. Kolmychek, et al., Phys. Rev. B 96 (2017) 075408. doi: 10.1103/PhysRevB.96.075408
44. [44]
  M.A. Kriech, J.C. Conboy, J. Am. Chem. Soc. 127 (2005) 2834–2835. doi: 10.1021/ja0430649
45. [45]
  L. Lin, T. Wang, Z. Lu, et al., J. Phys. Chem. C 118 (2014) 6726–6733. doi: 10.1021/jp4106579
46. [46]
  Y. Zhang, C. Yu, L. Han, et al., J. Phys. Chem. Lett. 13 (2022) 3523–3528. doi: 10.1021/acs.jpclett.2c00657
47. [47]
  F. Min, P. Zhou, Z. Huang, et al., Angew. Chem. Int. Ed. 60 (2021) 16547–16553. doi: 10.1002/anie.202103765
48. [48]
  H.H. Wang, H.Y. Liu, F. Cheng, et al., Chin. Chem. Lett. 29 (2018) 1404–1408. doi: 10.1016/j.cclet.2017.12.027
49. [49]
  M.A. Castriciano, S. Cardillo, R. Zagami, et al., Int. J. Mol. Sci. 22 (2021) 797. doi: 10.3390/ijms22020797
50. [50]
  B.M. Weon, J.H. Je, Phys. Rev. E 82 (2010) 015305. doi: 10.1103/PhysRevE.82.015305
51. [51]
  K.X. Li, T.L. Zhang, H.Z. Li, et al., Acta Phys. Chim. Sin. 36 (2020) 1911057.
52. [52]
  D.C. Hooper, A.G. Mark, C. Kuppe, et al., Adv. Mater. 29 (2017) 1605110. doi: 10.1002/adma.201605110
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