- Crystal structures of anti- and syn-9,10-di(1′-naphthyl)anthracene and isomerization in solid state
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9,10-Di-(1′-naphthyl)anthracene is often used as electroluminescence materials in organic light-emitting diodes. Because of the hindered rotation about the σ-bond between naphthyl and anthracene chromophore, two possible stereoisomers can be isolated. HPLC, 1H NMR, and 13C NMR spectra gave two different sets of peaks and the X-ray single crystal analysis confirmed the structures of the two isomers, anti and syn. syn was more soluble than anti in THF as well as toluene and the thermal properties of the two were quite different. Differential scanning calorimetry study and HPLC analysis showed that the isomerization between anti and syn in the solid state took place at >370 °C.
- Lee, Cho Hee,Kim, Mi Jong,Han, Sang-Pil,Lee, Yoo-Soon,Kang, Sung Kwon,Song, Jae Hee,Je, Jong Tae,Oh, Hyoung-Yun,Kim, Yeong-Joon
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- Synthesis of 9,10-Diarylanthracenes via Mg(TMP) 2 ·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
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A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.
- Miyamoto, Naoya,Nakazawa, Yuki,Nakamura, Takanori,Okano, Kentaro,Sato, Sota,Sun, Zhe,Isobe, Hiroyuki,Tokuyama, Hidetoshi
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p. 513 - 518
(2017/12/08)
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- Synthesis and characterization of polyaromatic compounds using tri(naphthyl)indium
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(Chemical Equation Presented) A variety of polyaromatic compounds bearing 1- and 2-naphthyl groups were prepared from the reactions of corresponding halides with tri(1- and 2-naphthyl)indium in good to excellent yields. Thermal, photophysical and electrochemical behaviors of carbazoles having naphthyl groups were studied. They have shown to be promising host and hole transporting materials in organic electroluminescence due to their high thermal stability, electrochemical reversibility and wide band gap.
- Lee, Wonhyung,Kang, Youngjin,Lee, Phil Ho
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p. 4326 - 4329
(2008/09/21)
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