Dihalo-substituted dibenzopentalenes: their practical synthesis and transformation to dibenzopentalene derivatives |
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Authors: | Feng Xu Lifen Peng Akihiro Orita Junzo Otera |
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Institution: | Department of Applied Chemistry, Okayama University of Science , Kita-ku, Okayama 700-0005, Japan. |
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Abstract: | Diiodo- and bromo, iodo-substituted dibenzopentalenes were obtained by treatment of 5,6,11,12-tetradehydrodibenzoa,e]cyclooctene with I(2) and IBr, respectively. These dihalo-substituted pentalenes reacted with terminal ethynes in Sonogashira coupling and with arylboronic acid in Suzuki-Miyaura coupling to give a series of phenylethynyl- and/or aryl-substituted pentalenes. Suzuki-Miyaura coupling of the halopentalenes with in situ prepared pentaleneboronic esters provided bis-, tri-, and tetra(dibenzopentalene)s. It was found that these dibenzopentalene oligomers underwent facile electrochemical reduction and exhibited a bathochromic shift in UV-vis absorption spectra because of their expanded π-systems. |
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