10-Mesityl-1,8-diphenylanthracene Dimer. Synthesis, Structure, and Properties

10-Mesityl-1,8-diphenylanthracene Dimer. Synthesis, Structure, and Properties
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10-异丙基-1,8-二苯基蒽二聚体。

DOI:
10.1021/acs.joc.8b00200
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发表时间:
2018
期刊:
影响因子:
3.6
通讯作者:
M. Iyoda
M. Iyoda
中科院分区:
化学2区
文献类型:
--
作者:
A. Shirai;H. Sano;Y. Nakamura;M. Takashika;H. Otani;M. Hasegawa;S. Kato;M. Iyoda

文献摘要

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利用1,8-双(4-溴苯基)-10-异三甲苯基-蒽7衍生的Lipshutz铜酸盐的电子转移氧化合成了大环10-异三甲苯基-1,8-二苯基蒽二聚体4,收率中等。该二聚体 4 是一种荧光性很强的分子 (ΦF0.40),具有较高的热稳定性、光稳定性和空气稳定性。 X射线分析显示4具有独特的结构,内腔较小,可以掺入小分子或原子。溶液中的1H NMR谱和固态4的发射光谱表明,铜(I)离子被掺入形成1:1络合物4·CuOTf,而银(I)离子在相似条件下仅与4发生微弱的相互作用。
Macrocyclic 10-mesityl-1,8-diphenylanthracene dimer4was synthesized by using the electron-transfer oxidation of Lipshutz cuprate derived from 1,8-bis(4-bromophenyl)-10-mesityl-anthracene7in moderate yield. This dimer4is a considerably fluorescent molecule (ΦF0.40) with high thermal, photo, and air stability. The X-ray analysis of4revealed a unique structure with a small inner cavity which can incorporate a small molecule or atom.1H NMR spectra in solution and emission spectra of4in the solid state showed that copper(I) ion was incorporated to form a 1:1 complex4·CuOTf, whereas silver(I) ion only weakly interacted with4under similar conditions.