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Desymmetrized Vertex Design toward a Molecular Cage with Unusual Topology
Author(s) -
Zhang Lei,
Jin Yinghua,
Tao GuoHong,
Gong Yu,
Hu Yiming,
He Ling,
Zhang Wei
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007454
Subject(s) - intramolecular force , cage , vertex (graph theory) , topology (electrical circuits) , crystallography , chemistry , hydrogen bond , molecule , crystal structure , crystal engineering , materials science , nanotechnology , stereochemistry , organic chemistry , computer science , combinatorics , graph , mathematics , theoretical computer science
A novel low‐symmetry organic molecular cage with distinctive geometry was successfully synthesized from 5,5′‐(propane‐2,2‐diyl)bis(2‐hydroxyisophthalaldehyde) and 1,2‐cyclohexanediamine building blocks, through the desymmetrized vertex design strategy. Single‐crystal X‐ray crystallographic analysis shows that the cage contains asymmetrical and nonplanar windows, exhibiting an unprecedented C 2 symmetry and an efficient packing. The molecular cage structure was also characterized by FTIR, NMR, and MALDI‐TOF. Quantum chemistry studies show that the cage structure contains rare intramolecular hydrogen‐hydrogen (C−H⋅⋅⋅H−C) bonding interactions. The cage crystals exhibit high iodine vapor uptake (3.78 g g −1 ), which is among the highest for porous molecular materials. The knowledge gained in this study would open new possibilities for the design and synthesis of molecular cages with novel topologies targeting a broad range of applications.