Conformational and Optical Characteristics of Unidirectionally Twisted Binaphthyl-Bipyridyl Cyclic Dyads.
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).
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.|‡Elements Chemistry Laboratory, RIKEN, and Advanced Elements Chemistry Research Team, RIKEN, Center for Sustainable Resource Science (CSRS), Wako, 351-0198, Japan.
Kazuto
K
Takaishi
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.
Jun
J
Suzuki
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.
Tatsuya
T
Yabe
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.
Hikaru
H
Asano
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.
Michihiro
M
Nishikawa
§Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science (CEMS), Wako 351-0198, Japan.
Daisuke
D
Hashizume
‡Elements Chemistry Laboratory, RIKEN, and Advanced Elements Chemistry Research Team, RIKEN, Center for Sustainable Resource Science (CSRS), Wako, 351-0198, Japan.
Atsuya
A
Muranaka
‡Elements Chemistry Laboratory, RIKEN, and Advanced Elements Chemistry Research Team, RIKEN, Center for Sustainable Resource Science (CSRS), Wako, 351-0198, Japan.|∥Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Masanobu
M
Uchiyama
†Faculty of Science and Technology, Seikei University, Musashino, Tokyo 180-8633, Japan.
Akihiro
A
Yokoyama
D015082:2,2'-Dipyridyl / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D012996:Solutions
D009281:Naphthalenes; D012996:Solutions; D015082:2,2'-Dipyridyl