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Synthesis, Properties and Redox Behavior of Ene–Diyne Scaffolds Bearing 1‐ and 2‐Azulenyl Groups at the Periphery
Author(s) -
Shoji Taku,
Shimomura Erika,
Maruyama Mitsuhisa,
Ito Shunji,
Okujima Tetsuo,
Morita Noboru
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201397
Subject(s) - chemistry , redox , sonogashira coupling , differential pulse voltammetry , ene reaction , cyclic voltammetry , fluorene , photochemistry , azulene , medicinal chemistry , electrochemistry , palladium , catalysis , organic chemistry , electrode , polymer
Ene–diyne systems possessing 1‐ and 2‐azulenyl groups at the periphery were prepared by palladium‐catalyzed cross‐coupling reaction of 1‐ and 2‐ethynylazulenes with 9‐dibromomethylene‐9 H ‐fluorene and 9,10‐bis(dibromomethylene)‐9,10‐dihydroanthracene or 2‐iodoazulene with 9,10‐bis(diethynylmethylene)‐9,10‐dihydroanthracene under Sonogashira–Hagihara conditions. The redox behavior of the ene–diyne compounds was examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). Moreover, a significant color change of the ene–diyne derivatives was observed with visible spectroscopy under electrochemical reduction conditions.