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

doi:10.1016/j.tetlet.2007.11.179

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

Department of Integrated Materials

Research output: Contribution to journal › Article › peer-review

36 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 language	English
Pages (from-to)	772-776
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2007.11.179
Publication status	Published - Jan 28 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.11.179

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

Research output: Contribution to journal › Article › peer-review

Suzuki, T, Ohta, K, Nehira, T, Higuchi, H, Ohta, E, Kawai, H & Fujiwara, K 2008, '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', Tetrahedron Letters, vol. 49, no. 5, pp. 772-776. https://doi.org/10.1016/j.tetlet.2007.11.179

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title = "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",

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.",

author = "Takanori Suzuki and Kenji Ohta and Tatsuo Nehira and Hiroki Higuchi and Eisuke Ohta and Hidetoshi Kawai and Kenshu Fujiwara",

note = "Funding Information: National Research Institute of Brewing is gratefully acknowledged for use of the FDCD instrument. This work was partly supported by the Global COE Program (Project No. B01: Catalysis as the Basis for Innovation in Materials Science) from the Ministry of Education, Science and Technology, Japan. ",

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AU - Suzuki, Takanori

AU - Ohta, Kenji

AU - Nehira, Tatsuo

AU - Higuchi, Hiroki

AU - Ohta, Eisuke

AU - Kawai, Hidetoshi

AU - Fujiwara, Kenshu

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AB - 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.

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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

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