Solvent-sensitive circularly polarized luminescent compounds bearing a 9,9'-spirobi[fluorene] skeleton.,Organic & Biomolecular Chemistry

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Solvent-sensitive circularly polarized luminescent compounds bearing a 9,9'-spirobi[fluorene] skeleton.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-15 , DOI: 10.1039/c9ob02681a
Masahiro Kubo ₁ , Ko Takase ₁ , Keiichi Noguchi ₂ , Koji Nakano ₁

Affiliation

A series of chiral 9,9'-spirobi[fluorene] (SBF) derivatives with diphenylamino donor and cyano acceptor units were designed as a new family of circularly polarized luminescent materials. The designed SBF derivatives were successfully synthesized from 7,7'-dibromo-9,9'-spirobi[fluorene]-2,2'-diol. No racemization occurred in the synthetic sequence. Therefore, each enantiomer of the SBF derivatives can be prepared from the enantiomerically pure starting material. Absorption and fluorescence spectroscopy and theoretical calculations revealed that the phenylene linker between the donor/acceptor units and the SBF core has a great impact on their photophysical properties. In particular, the phenylene linker was found to induce a red shift in their emission bands. The obtained chiral SBF derivatives exhibited solvent-dependent circularly polarized luminescence owing to their donor-π-acceptor structures.

中文翻译：

带有9,9'-螺双[芴]骨架的溶剂敏感型圆极化发光化合物。

设计了一系列具有二苯氨基供体和氰基受体单元的手性9,9'-螺双[芴]（SBF）衍生物，作为新的圆偏振发光材料系列。从7,7'-二溴-9,9'-螺双[芴] -2,2'-二醇成功合成了设计的SBF衍生物。在合成序列中未发生外消旋作用。因此，可以从对映体纯的起始原料制备SBF衍生物的每种对映体。吸收光谱和荧光光谱以及理论计算表明，供体/受体单元与SBF核之间的亚苯基连接基对其光物理性质有很大影响。特别地，发现亚苯基接头在其发射带中引起红移。

更新日期：2020-04-24

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