Synthesis of a Mechanically Planar Chiral and Axially Chiral [2]Rotaxane

Shinya Tajima; Atsuya Muranaka; Masaya Naito; Noriho Taniguch; Mei Harada; Shinobu Miyagawa; Masahiro Ueda; Hikaru Takaya; Nagao Kobayashi; Masanobu Uchiyama; Yuji Tokunaga

doi:10.1021/acs.orglett.1c02983

Synthesis of a Mechanically Planar Chiral and Axially Chiral [2]Rotaxane

Org Lett. 2021 Nov 19;23(22):8678-8682. doi: 10.1021/acs.orglett.1c02983. Epub 2021 Nov 3.

Authors

Affiliations

¹ Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan.
² Molecular Structure Characterization Unit, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
³ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁴ International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji 611-0011, Japan.
⁵ Institute for Molecular Science, National Institute of Natural Science, Nishigo-Naka, Myodaiji, Okazaki 444-8585, Japan.
⁶ Faculty of Textile Science and Technology, Shinshu University, Tokida, Ueda, Nagano 386-8567, Japan.

PMID: 34730985
DOI: 10.1021/acs.orglett.1c02983

Abstract

In this study, we synthesized a [2]rotaxane that was both mechanically planar chiral and axially chiral, comprising a symmetrical bis-crown ether featuring a biphenyl moiety (as the macrocyclic component) and a symmetrical bis-ammonium salt (as the dumbbell-shaped component).