Shape-persistency and molecular function in heteromacrocycles: creation of heteroarenecyclynes and arene-azaarenecyclynes.
On the basis of our concept that the introduction of heteroatoms and shape-persistency into the pi-macrocycles should bring forth striking functions or properties, heteroarenecyclynes (such as oxaarenecyclynes and thiaarenecyclynes) with semi-shape-persistent structure, and arene-azaarenecyclynes with shape-persistent structure have been prepared. Their novel functions and characteristic properties are disclosed. Noteworthy is that heteroarenecyclynes include C(60) to provide a Saturn-type complex with a N(2) binding function. A simple member of the oxaarenecyclyne compounds undergoes the Ag(I)-induced cyclization leading to the quantitative formation of strongly luminescent perylene derivative. Arene-azaarenecyclynes are versatile compounds. For example, they exhibit intense luminescence in spite of the meta-bonding structure, providing the circular luminophore. Also they serve as receptors for special metal, organic, and inorganic substrates. The observed molecular functions are valuable for scientific and practical application.
Yamaguchi
Yoshihiro
Y
Kinki University, Faculty of Science and Engineering, Department of Chemistry, 3-4-1 Kowakae, Higashi-Osaka 577-8502, Japan. yamaguch@chem.kindai.ac.jp
Yoshida
Zen-ichi
Z