An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties
An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties
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DOI：
10.1039/c9cc03510a
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发表时间：
2019-08-21
影响因子：
4.9
通讯作者：
Itami, Kenichiro
中科院分区：
文献类型：
--
作者：
Chaolumen;Ito, Hideto;Itami, Kenichiro
手性有机π共轭分子在手性电子材料和器件领域有着广泛的应用。本文报道了一个新的轴向手性1，1 '-联甘菊环及其π-延伸衍生物的模体，其中联苯被甘菊环的富电子五元环化.这两个化合物是由2-三联苯甘菊环通过逐步分子间和分子内氧化C-H/ C-H偶联反应合成的。X射线衍射分析表明，两种化合物的晶体都含有一对映体。此外，轴向手性1，1 '-联甘菊环衍生物被成功地分离成对映异构体，表现出清晰的镜像圆二色性光谱直到近红外区域。
Chiral organic pi-conjugated molecules have been intensively investigated in the fields of chiral electronic materials and devices. Herein we report a new motif for an axially chiral 1,1'-biazulene and its pi-extended derivative, in which biphenyl was annulated by the electron-rich five-membered-ring of the azulene moiety. These two compounds were unexpectedly synthesized from 2-terphenyl azulene by stepwise intermolecular and intramolecular oxidative C-H/ C-H couplings. X-ray diffraction analysis revealed that the crystals of both compounds contain a pair of enantiomers. Furthermore, the axially chiral 1,1'-biazulene derivatives were successfully separated into enantiomers that exhibited clear mirror-image circular dichroism spectra up to the near-infrared region.