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| 基本情報 |
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| 氏名 |
赤司 治夫 |
| 氏名（カナ） |
ｱｶｼ ﾊﾙｵ |
| 氏名（英語） |
Akashi Haruo |
| 所属 |
機構 研究社会連携機構 ﾌﾛﾝﾃｨｱ理工学研 |
| 職名 |
教授 |
| researchmap研究者コード |
1000113819 |
| researchmap機関 |
岡山理科大学 |
Synthesis of (Z)-Enediynes via Stereoinvertive Nucleophilic Substitution of (E)-Sulfonylethenes with Arylethynide, and Their Aggregation-Induced Optical Properties
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.
The Journal of Organic Chemistry
American Chemical Society (ACS)
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