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

31 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

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Chirality
Amides
Hydrogen
Hydrogen bonds
Fluorescence
diphenyl

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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

In: Tetrahedron Letters, Vol. 49, No. 5, 28.01.2008, p. 772-776.

Research output: Contribution to journalArticle

Suzuki, Takanori ; Ohta, Kenji ; Nehira, Tatsuo ; Higuchi, Hiroki ; Ohta, Eisuke ; Kawai, Hidetoshi ; Fujiwara, Kenshu. / 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. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 5. pp. 772-776.
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AU - Fujiwara, Kenshu

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