Synthesis and Photophysical Properties of a 13,13′-Bibenzo[b]perylenyl Derivative as a π-Extended 1,1′-Binaphthyl Analog

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• 作者：Yosuke Uchida ; Takashi Hirose ; Takuya Nakashima ; Tsuyoshi Kawai ; Kenji Matsuda
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2118-2121
• 全文大小：393K
• 年卷期：0
• ISSN：1523-7052

文摘

A 13,13′-bibenzo[b]perylenyl derivative—an axially chiral π-extended compound in which two perylene subunits fused to 1,1′-binaphthyl scaffold—has been synthesized from 1,8-dibromophenanthrene using an anionic cyclodehydrogenation reaction in the presence of potassium metal as the key step. The pair of enantiomers can be separated by chiral high-performance liquid chromatography (HPLC), which showed a strong circular dichroism (CD) (Δε = 330 M^–1 cm^–1 at 449 nm, |g_CD| = 5.8 × 10^–3 at 453 nm), high fluorescence quantum yield (Φ_f = 64%), and strong circular polarized luminescence (CPL) (|g_CPL| = 5 × 10^–3 at 454 nm) in solution phase.