Construction and charge-transfer complexation of adamantane-based macrocycles and a cage with aromatic ring moieties.
Adamantane-based macrocycles and a cage with aromatic ring moieties have been developed and structurally revealed by X-ray crystallographic analysis. The dimerized (1) and trimerized (2) macrocycles of binary molecules based on adamantane with acetylenic aromatic ring moieties were designed and effectively synthesized. Similarly, a cryptand-like macrobicyclic cage (3) was constructed from a trisubstituted adamantane derivative. Single-crystal X-ray analysis revealed that both cyclic compounds have nearly a rectangular shape with or without a solvent molecule in the cavity. The macrobicyclic cage has an inner space and accommodates a chloroform molecule via C-H...pi interactions. Macrocycles and cage encapsulate 1,3,5-trinitrobenzene (4) as an electron-poor guest in a one-to-one complex via charge-transfer interactions in a parallel fashion, and showed the formation of molecular networks such as columns, tubes, 2D layers, and 3D networks composed of two different types through noncovalent interactions in the solid state.
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan. tominagam@kph.bunri-u.ac.jp
Masahide
M
Tominaga
Hyuma
H
Masu
Isao
I
Azumaya
D000218:Adamantane / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019281:Dimerization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D001555:Benzene Derivatives; D047028:Macrocyclic Compounds; D000218:Adamantane