Characterization and enantiomer separation of indene-derived hexacyclic hydrocarbon and its application as a chiral source. (7th May 2021)

• Record Type: Journal Article
• Authors: Kodama, Koichi; Yamaguchi, Shohei; Hayano, Shigetaka; Houkawa, Takashi; Kitahara, Yoshinori; Shitara, Hiroaki; Hirose, Takuji
• Is Part Of: Tetrahedron. Volume 87(2021)
• Publication Date: 2021-05-07
• Subjects: Enantioseparation -- Hydrocarbon -- Polycyclic compound -- Chirality -- Chiral dopant; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132082
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A hexacyclic chiral aromatic hydrocarbon (1 ), obtained by the reaction between indene and cyclopentadiene, has been characterized, and its enantioseparation has been achieved by the combination of stereoselective complexation with β-cyclodextrin and recrystallization. This method has been applied in the large-scale production of both pure enantiomers of 1 . Enantiopure 1 and its derivatives have been used as chiral dopants in nematic liquid crystals. Graphical abstract: Image 1 Highlights: Characterization of a rigid hexacyclic chiral hydrocarbon with conglomerate nature. Enantiomer separation by selective complexation with β-cyclodextrin and recrystallization. Application of its derivatives as chiral dopants for nematic liquid crystals.