Yuta Akagi, Hikaru Watanabe, Toshiki Sakami, Sou Furumatsu, Shunsuke Yamada, Ryosuke Maki, Yasuhiro Okuda, Haruo Akashi, Kan Wakamatsu, Yoshihiro Kusano, Akihiro Orita
(Z)-Enediynes were successfully synthesized from a trio of terminal ethynes through consecutive three-step reactions: iodosulfonylation of ethyne with I2/PhSO2Na, followed by ethynylations of iodo and sulfonyl moieties of the resulting iodosulfonylethene via Sonogashira−Hagihara coupling and nucleophilic addition–elimination, respectively. The molecular structure of the obtained (Z)-enediyne was fully characterized by X-ray crystal structure analysis, revealing that the nucleophilic substitution of (E)-sulfonylethene with arylethynide underwent a selective stereoinversion. The (Z)-enediynes exhibited photoluminescence in both the solution and solid states (crystals and powders). Ph2N-substituted derivatives showed remarkable solvatofluorochromism, and upon replacing the solvent from toluene to acetonitrile, the emission color changed from blue to yellow.
Research papers (academic journals)
