Premium
One‐Pot and Shape‐Controlled Synthesis of Organic Cages
Author(s) -
Zhao Xiang,
Liu Yue,
Zhang ZhiYuan,
Wang Yiliang,
Jia Xueshun,
Li Chunju
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104875
Subject(s) - monomer , chemistry , triphenylamine , covalent bond , toluene , benzene , methylcyclohexane , moiety , condensation , polymer chemistry , organic chemistry , polymer , physics , thermodynamics
Organic cages are fascinating because of their well‐defined 3D cavities, excellent stability, and accessible post‐modification. However, the synthesis is normally realized by fragment coupling approach in low yields. Herein, we report one‐pot, gram‐scale and shape‐controlled synthesis of two covalent organic cages (box‐shaped [4]cage and triangular prism‐shaped [2]cage) in yields of 46 % and 52 %, involving direct condensation of triangular 1,3,5‐tris(2,4‐dimethoxyphenyl)benzene monomer with paraformaldehyde and isobutyraldehyde, respectively. The cages can convert into high‐yielding per‐hydroxylated analogues. The [2]cage can be utilized as gas chromatographic stationary phase for high‐resolution separation of benzene/cyclohexane and toluene/methylcyclohexane. By changing the central moiety of the triangular monomer and/or aldehyde, this synthetic method would have the potential to be a general strategy to access diverse cages with tunable shape, size, and electronic properties.