Chirality induction by formation of assembled structures based on anion-responsive π-conjugated molecules

Hiromitsu Maeda, Wataru Hane, Yuya Bando, Yoshitaka Terashima, Yohei Haketa, Hiroshi Shibaguchi, Tsuyoshi Kawai, Masanobu Naito, Kazuto Takaishi, Masanobu Uchiyama, Atsuya Muranaka

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Anion-responsive π-conjugated compounds having chiral alkyl chains were synthesized. Circular dichroism (CD) and circularly polarized luminescence (CPL) were observed in the solution-state assemblies of the chiral anion receptors and those of their anion complexes as salts of a planar triazatriangulenium cation. The CD and CPL spectral patterns of the ion-pair-based assemblies were completely opposite to those of the anion-free assemblies, and this suggests that anion binding and subsequent ion pairing change the chirality of the assembly modes. Opposite signs of the circular dichroism (CD) and circularly polarized luminescence (CPL) spectral patterns of ion-pair-based assemblies and anion-free assemblies of anion-responsive π-conjugated compounds bearing chiral alkyl chains (see figure) suggest that anion binding and subsequent ion pairing change the chirality of the assembly modes.

Original languageEnglish
Pages (from-to)16263-16271
Number of pages9
JournalChemistry - A European Journal
Volume19
Issue number48
DOIs
Publication statusPublished - Nov 25 2013
Externally publishedYes

Keywords

  • anion receptors
  • chirality
  • ion pairs
  • stacking interactions
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Chirality induction by formation of assembled structures based on anion-responsive π-conjugated molecules'. Together they form a unique fingerprint.

  • Cite this

    Maeda, H., Hane, W., Bando, Y., Terashima, Y., Haketa, Y., Shibaguchi, H., Kawai, T., Naito, M., Takaishi, K., Uchiyama, M., & Muranaka, A. (2013). Chirality induction by formation of assembled structures based on anion-responsive π-conjugated molecules. Chemistry - A European Journal, 19(48), 16263-16271. https://doi.org/10.1002/chem.201301737