Citation: Ying Xiong, Chao Huang, Hongjuan Liu, Rui Yi, Bi-Xue Zhu, Xin-Long Ni. Tunable organic particles: An efficient approach from solvent-dependent Schiff base macrocycles[J]. Chinese Chemical Letters, ;2021, 32(11): 3522-3525. doi: 10.1016/j.cclet.2021.04.060 shu

Tunable organic particles: An efficient approach from solvent-dependent Schiff base macrocycles

Ying Xiong ^{a, b} ,
Chao Huang ^a ,
Hongjuan Liu ^a ,
Rui Yi ^a ,
Bi-Xue Zhu ^{a, *,} ,
Xin-Long Ni ^{a, c, *,}

a.
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China
b.
School of Chemistry and Materials, Guizhou Normal University, Guiyang 550025, China
c.
College of Chemistry and Chemical Engineering, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China

bxzhu@gzu.edu.cn

longni333@163.com

Received Date: 2 March 2021
Revised Date: 28 April 2021
Accepted Date: 30 April 2021
Available Online: 8 May 2021

Figures(4)

The synthesis of cyclopolymers upon controlling the degree of macrocyclic polymerization, followed by the discovery of new properties has attracted increasing attention in supramolecular chemistry. Herein, a Schiff-base condensation method performed at room temperature was used to control the formation of [1 + 1] and [2 + 2] macrocycles. In pure MeOH, the isomer [1 + 1] macrocycles were synthesized and organic particles such as dendritic, rods, and solid microspheres were directly precipitated from the reaction solution. The [1 + 1] macrocycles can be efficiently converted into their corresponding [2 + 2] macrocycles accompanied by the tunable morphology of the organic particles when n-hexane was added to the MeOH solution. Further studies showed that these organic particles have potential application toward the selective removal of Cd²⁺ ions with different adsorption ability in MeOH solution.
- Schiff base,
- Organic particles,
- Macrocycle,
- Noncovalent interaction,
- Self-assembly
1. [1]
  D. Horn, J. Rieger, Angew. Chem. Int. Ed.40 (2001) 4330-4361 doi: 10.1002/1521-3773(20011203)40:23<4330::AID-ANIE4330>3.0.CO;2-W
2. [2]
  S. Wagner, A. Gondikas, E. Neubauer, T. Hofmann, F. Kammer, Angew. Chem. Int. Ed. 53 (2014) 12398-12419 doi: 10.1002/anie.201405050
3. [3]
  J.F. Chen, E.S. Garcia, S.C. Zimmerman, Acc. Chem. Res. 53 (2020) 1244-1256 doi: 10.1021/acs.accounts.0c00178
4. [4]
  J.M. Zhou, X.F. Zhu, Q.Y. Cheng, et al., Inorg. Chem. 59 (2020) 9177-9187 doi: 10.1021/acs.inorgchem.0c01073
5. [5]
  D. Ding, K. Li, B. Liu, B.Z. Tang, Acc. Chem. Res. 46 (2013) 2441-2453 doi: 10.1021/ar3003464
6. [6]
  J. Qian, B.Z. Tang, Chem3 (2017) 56-91 doi: 10.1016/j.chempr.2017.05.010
7. [7]
  Y.L. Yan, Y.S. Zhao, Chem. Soc. Rev. 43 (2014) 4325-4340 doi: 10.1039/C4CS00098F
8. [8]
  K.S. Daskalakis, A.I. Väkeväinen, J.P. Martikainen, T.K. Hakala, P. Törmä, Nano Lett. 18 (2018) 2658-2665 doi: 10.1021/acs.nanolett.8b00531
9. [9]
  K. Li, B. Liu, Chem. Soc. Rev. 43 (2014) 6570-6597 doi: 10.1039/C4CS00014E
10. [10]
  M. Overchuk, G. Zheng, Biomaterials156 (2018) 217-237 doi: 10.1016/j.biomaterials.2017.10.024
11. [11]
  X. Fu, L. Hosta-Rigau, R. Chandrawati, J.W. Cui, Chem 4 (2018) 2084-2107. doi: 10.1016/j.chempr.2018.07.002
12. [12]
  Z. Wang, B. Guo, E. Middha, et al., ACS Appl. Mater. Interfaces11 (2019) 11167-11176 doi: 10.1021/acsami.8b22579
13. [13]
  L. Huang, Z.J. Li, Y. Zhao, et al., J. Am. Chem. Soc. 138 (2016) 14586-14591 doi: 10.1021/jacs.6b05390
14. [14]
  D.F. Liu, S. Cito, Y.Z. Zhang, et al., Adv. Mater. 27 (2015) 2298-2304 doi: 10.1002/adma.201405408
15. [15]
  J.P. Rao, K. E Geckeler, Prog. Polym. Sci. 36 (2011) 887-913
16. [16]
  [a] G.C. Yu, K.C. Jie, F.H. Huang, Chem. Rev. 115 (2015) 7240–7303.
  [b] T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31 (2020) 1–9.
  [c] S. Li, Y. Gao, Y. Ding, A. Xu, H. Tan, Chin. Chem. Lett. 32 (2021) 313–318.
  [d] Y. Hou, S. Li, Z. Zhang, L. Chen, M. Zhang, Polym. Chem. 11 (2020) 254–258.
17. [17]
  H.Y. Chen, C. Huang, Y.Z. Ding, et al., Chem. Sci. 10 (2019) 490–496 doi: 10.1039/c8sc03824d
18. [18]
  H.Y. Chen, C. Huang, Y.X. Deng, et al., ACS Nano13 (2019) 2840-2848 doi: 10.1021/acsnano.8b09478
19. [19]
  L.S. Shimizu, S.R. Salpage, A.A. Korous, Acc. Chem. Res. 47 (2014) 2116–2127 doi: 10.1021/ar500106f
20. [20]
  Q. Yu, X.D. Zhang, S.T. Wu, et al., Chem. Commun. 56 (2020) 2304–2307 doi: 10.1039/c9cc09540c
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