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

Research output: Contribution to journalArticle

8 Citations (Scopus)

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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2,2'-Dipyridyl
twisting
chirality
dichroism
crystallization
solid state
augmentation
Chirality
Circular Dichroism
Crystallization

ASJC Scopus subject areas

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

Cite this

Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads. / Takaishi, Kazuto; Suzuki, Jun; Yabe, Tatsuya; Asano, Hikaru; Nishikawa, Michihiro; Hashizume, Daisuke; Muranaka, Atsuya; Uchiyama, Masanobu; Yokoyama, Akihiro.

In: Organic Letters, Vol. 17, No. 16, 12.08.2015, p. 4098-4101.

Research output: Contribution to journalArticle

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, vol. 17, no. 16, pp. 4098-4101. https://doi.org/10.1021/acs.orglett.5b02041
Takaishi, Kazuto ; Suzuki, Jun ; Yabe, Tatsuya ; Asano, Hikaru ; Nishikawa, Michihiro ; Hashizume, Daisuke ; Muranaka, Atsuya ; Uchiyama, Masanobu ; Yokoyama, Akihiro. / Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads. In: Organic Letters. 2015 ; Vol. 17, No. 16. pp. 4098-4101.
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