Unprecedented four-way-output molecular response system based on biphenyl-2,2′-diyldiacridiniums: induction of axial chirality through intramolecular hydrogen bonds between chiral amide groups

Takanori Suzuki, Kenji Ohta, Tatsuo Nehira, Hiroki Higuchi, Eisuke Ohta, Hidetoshi Kawai, Kenshu Fujiwara

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Upon the attachment of N-(R)-2-phenylethylamide moieties to the acridinium units of the title dication, intramolecular hydrogen bonds induce a diastereomeric preference in terms of axial chirality (70% de at -40 °C in CH2Cl2). Thus, external stimuli induce not only UV-vis and fluorescence spectra changes but also changes in the CD and fluorescence-detected CD (FDCD) spectra, realizing unprecedented four-way-output molecular response systems.

Original languageEnglish
Pages (from-to)772-776
Number of pages5
JournalTetrahedron Letters
Volume49
Issue number5
DOIs
Publication statusPublished - Jan 28 2008

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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