Synthesis of thiophene-containing hybrid calixphyrins of the 5,10-porphodimethene type.
The synthesis, structure, and optical and electrochemical properties of thiophene-containing hybrid calixphyrins are reported. The 5,10-porphodimethene type 14pi- and 16pi-S,N2,X-hybrid calixphyrins (X = NH, O, S) were prepared by acid-promoted dehydrative condensation between a thiatripyrrane and the corresponding 2,5-bis[hydroxy(phenyl)methyl]heteroles followed by DDQ oxidation. Both crystallographic and spectroscopic analyses of the newly prepared hybrid calixphyrins have revealed that the combination of heteroles explicitly influences the electronic structures of the pi-conjugated framework. The 14pi-S,N2,X-hybrid calixphyrins have proven to be fluorescent in solution.
Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan. matano@scl.kyoto-u.ac.jp
Yoshihiro
Y
Matano
Tooru
T
Miyajima
Noriaki
N
Ochi
Yoshihide
Y
Nakao
Shigeyoshi
S
Sakaki
Hiroshi
H
Imahori
D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis*; D013876:Thiophenes / Q000737:chemistry*
D011166:Porphyrins; D013876:Thiophenes