A Chiral Recognition System Orchestrated by Self‐Assembly: Molecular Chirality, Self‐Assembly Morphology, and Fluorescence Response,Angewandte Chemie International Edition

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A Chiral Recognition System Orchestrated by Self‐Assembly: Molecular Chirality, Self‐Assembly Morphology, and Fluorescence Response
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-08-28 , DOI: 10.1002/anie.201706142
Takao Noguchi _{1,

2,

3} , Bappaditya Roy ₁ , Daisuke Yoshihara ₃ , Junji Sakamoto ₃ , Tatsuhiro Yamamoto ₃ , Seiji Shinkai _{1,

3}

Affiliation

The newly developed oligophenylenevinylene (OPV)‐based fluorescent (FL) chiral chemosensor (OPV‐Me) for the representative enantiomeric guest, 1,2‐cyclohexanedicarboxylic acid (1,2‐CHDA: RR‐ and SS‐form) showed the high chiral discrimination ability, resulting in the different aggregation modes of OPV‐Me self‐assembly: RR‐CHDA directed the fibrous supramolecular aggregate, whereas SS‐CHDA directed the finite aggregate. The consequent FL intensity toward RR‐CHDA was up to 30 times larger than that toward SS‐CHDA. Accordingly, highly enantioselective recognition was achieved. Application to the chirality sensing was also possible: OPV‐Me exhibited a linear relationship between the FL intensity and the enantiomeric excess through the morphological development of stereocomplex aggregates. These results clearly show that the chiral recognition ability is manifested by the amplification cascade of the chirality difference through self‐assembly.

中文翻译：

自组装精心设计的手性识别系统：分子手性，自组装形态和荧光响应

新开发的基于低聚亚苯基亚乙烯基（OPV）的荧光（FL）手性化学传感器（OPV-Me）用于代表性对映体1,2-环己烷二甲酸（1,2-CHDA：RR和SS形式）具有高手性区分能力，导致OPV-Me自组装的聚集方式不同：RR - CHDA定向纤维超分子聚集体，而SS- CHDA定向有限聚集体。因此，对RR ‐CHDA的FL强度比对SS的FL强度大30倍。‐CHDA。因此，实现了高度对映选择性识别。也可以应用于手性传感：OPV-Me通过立体复合物聚集体的形态发展在FL强度和对映体过量之间表现出线性关系。这些结果清楚地表明，通过自组装，手性差异的放大级联表现出手性识别能力。

更新日期：2017-08-28

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