Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads

Kazuto Takaishi, Jun Suzuki, Tatsuya Yabe, Hikaru Asano, Michihiro Nishikawa, Daisuke Hashizume, Atsuya Muranaka, Masanobu Uchiyama, Akihiro Yokoyama

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Abstract

An axially chiral binaphthyl-bipyridyl cyclic dyad in which the two units are connected by short -CH2O- linkers was synthesized. Experimental and theoretical analyses indicate that the (R)-binaphthyl unit in the dyad induces (R)-chirality in the bipyridyl unit, both in the solid state and in solution. It is shown that vibrational circular dichroism (VCD) is useful to determine the twisting pattern of 2,2′-bipyridyl compounds. The dyad shows crystallization-induced emission enhancement (CIEE).

Original languageEnglish
Pages (from-to)4098-4101
Number of pages4
JournalOrganic Letters
Volume17
Issue number16
DOIs
Publication statusPublished - Aug 12 2015
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Takaishi, K., Suzuki, J., Yabe, T., Asano, H., Nishikawa, M., Hashizume, D., Muranaka, A., Uchiyama, M., & Yokoyama, A. (2015). Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads. Organic Letters, 17(16), 4098-4101. https://doi.org/10.1021/acs.orglett.5b02041