Citation: Yu Pang, Min Wang, Ning-Hua Yang, Min Xue, Yong Yang. One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure[J]. Chinese Chemical Letters, ;2024, 35(10): 109575. doi: 10.1016/j.cclet.2024.109575 shu

One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure

Yu Pang ^a ,
Min Wang ^a ,
Ning-Hua Yang ^b ,
Min Xue ^{a, *,} ,
Yong Yang ^{b, *,}

a.
School of Science, Department of Physics, Key Laboratory of Optical Field Manipulation of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China
b.
School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China

minxue@zstu.edu.cn

yangyong@zstu.edu.cn

Received Date: 30 September 2023
Revised Date: 15 January 2024
Accepted Date: 28 January 2024
Available Online: 29 January 2024

Figures(3)

Trifluoroacetic acid (TFA) catalyzed condensation reaction between tetraaminooxacalix[4]arene and N-alkylcarbazole-3,6-dicarbaldehyde in CH₂Cl₂ afforded a single product in 87%–89% yield. Well-defined yet undissolvable ¹H NMR spectra suggested formation of robust and discrete structures in solution. X-ray single crystal analysis further revealed a giant twisted double-layer chiral macrocycle in the solid state, which was formed from [4 + 8] condensation of the two reactants via 16 imine bonds. DFT calculations discovered that only the [4 + 8] twisted product is thermodynamically favorable, which accounts for its highly selective and efficient formation out of a library of many other combinations.
- One-pot synthesis,
- Oxacalix[4]arene,
- Dynamic covalent chemistry,
- Chiral macrocycle,
- X-ray single crystal
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