Communication

Asymmetric Induction in the Preparation of Helical Receptor–Anion Complexes: Ion-Pair Formation with Chiral Cations†

  1. Dr. Yohei Haketa1,
  2. Yuya Bando1,
  3. Dr. Kazuto Takaishi2,3,
  4. Prof. Dr. Masanobu Uchiyama2,4,
  5. Dr. Atsuya Muranaka2,5,
  6. Prof. Dr. Masanobu Naito5,6,7,
  7. Hiroshi Shibaguchi6,
  8. Prof. Dr. Tsuyoshi Kawai6,
  9. Prof. Dr. Hiromitsu Maeda1,*

Article first published online: 28 JUN 2012

DOI: 10.1002/anie.201202196

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 32, pages 7967–7971, August 6, 2012

Additional Information

How to Cite

Haketa, Y., Bando, Y., Takaishi, K., Uchiyama, M., Muranaka, A., Naito, M., Shibaguchi, H., Kawai, T. and Maeda, H. (2012), Asymmetric Induction in the Preparation of Helical Receptor–Anion Complexes: Ion-Pair Formation with Chiral Cations. Angew. Chem. Int. Ed., 51: 7967–7971. doi: 10.1002/anie.201202196

Author Information

  1. 1

    College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu 525–8577 (Japan)

  2. 2

    Advanced Elements Chemistry Research Team, RIKEN-ASI, Wako 351–0198 (Japan)

  3. 3

    Faculty of Science and Technology, Seikei University, Musashino 180–8633 (Japan)

  4. 4

    Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113–0033 (Japan)

  5. 5

    PRESTO (Japan) Science and Technology Agency (JST), Kawaguchi 332–0012 (Japan)

  6. 6

    Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Ikoma 630–0192 (Japan)

  7. 7

    National Institute for Materials Science (NIMS), Tsukuba 305–4047 (Japan)

*College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu 525–8577 (Japan)

  1. †

    This work was supported by PRESTO/JST (2007–2011), Grants-in-Aid for Young Scientists (B) (No. 21750155) and (A) (No. 23685032) from the MEXT, and Ritsumeikan R-GIRO project (2008–2013). We thank Prof. Takashi Ooi, Nagoya University, for the valuable suggestion for the preparation of chiral cations, Prof. Shuichi Hiraoka, the University of Tokyo, for the valuable discussion for the conversion of helical structures, Prof. Ryo Kitahara and Soichiro Kitazawa, Ritsumeikan University, for analysis of EXSY, the RIKEN Integrated Cluster of Clusters (RICC) for the computer resources, and Prof. Hitoshi Tamiaki and Prof. Tadashi Mizoguchi, Ritsumeikan University, for various measurements. Y.H. and Y.B. thank JSPS for a Research Fellowship for Young Scientists.

Publication History

  1. Issue published online: 1 AUG 2012
  2. Article first published online: 28 JUN 2012
  3. Manuscript Revised: 1 JUN 2012
  4. Manuscript Received: 20 MAR 2012

Funded by

  • MEXT
  • JSPS

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Keywords:

  • anion binding;
  • chirality;
  • chiroptical properties;
  • helical structures;
  • ion pairs
Thumbnail image of graphical abstract

Asymmetry through ion pairing: Upon addition of chloride and bromide ions, as chiral ammonium salts, to solutions of pyrrole-based π-conjugated linear oligomers, helical structures form with asymmetric induction, which is guided by the formation of diastereomeric ion pairs with chiral counter cations (see picture). These ions pairs exhibit circular dichroism (CD) and strong circularly polarized luminescence (CPL) with glum values of greater than 0.1.

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