Bicarbazoles: Systematic Structure鈥揚roperty Investigations on a Series of Conjugated Carbazole Dimers

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• 作者：Shin-ichiro Kato ; Hiroto Noguchi ; Atsushi Kobayashi ; Toshitada Yoshihara ; Seiji Tobita ; Yosuke Nakamura
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：October 19, 2012
• 年：2012
• 卷：77
• 期：20
• 页码：9120-9133
• 全文大小：624K
• 年卷期：v.77,no.20(October 19, 2012)
• ISSN：1520-6904

文摘

A large series of conjugated carbazole dimers, namely bicarbazoles 1鈥?b>12, were synthesized by Suzuki鈥揗iyaura, Sonogashira, Hay, and McMurry coupling reactions. In 1鈥?b>12, the two carbazole moieties are linked at the 1-, 2-, or 3-position directly or via an acetylenic or olefinic spacer. The structure鈥損roperty relationships, particularly the effects of the conjugation connectivity and the 蟺-conjugated spacers on the electronic, photophysical, and electrochemical properties of 1鈥?b>12, were studied by extensive UV鈥搗is and fluorescence spectroscopic measurements, cyclic voltammetry (CV), and theoretical calculations as well as X-ray crystallographic analyses. The connection at the 1-position of carbazole ensures high extent of 蟺-conjugation, while that at the 3-position enhances the electron-donating ability. Both acetylenic and olefinic spacers allow the extension of 蟺-conjugation, and the latter also causes the increase of the donor ability. Moreover, the structural variations were found to affect the fluorescence quantum yields significantly, which are up to 0.84.