Related Experiment Video
Updated: Jul 17, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
Inherently chiral molecular clips: synthesis, chiroptical properties, and application to chiral discrimination
Gaku Fukuhara1, Süreyya Madenci, Jolanta Polkowska
1ICORP Entropy Control Project, Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan.
Abstract:
Inherently chiral molecular clips (MCs), pseudoenantiomeric anti-1 and anti-2, as well as mesoid syn-3, were synthesized by diastereodifferentiating repetitive Diels-Alder reactions of the achiral bisdienophile 6 with chiral diene 5 generated in situ from (-)-menthyl 3,4-bis(dibromomethyl)benzoate 4. These MCs were successfully separated by chiral HPLC to give optically active anti-1 and anti-2 and almost optically inactive syn-3. The structures of anti-1, anti-2, and syn-3 were assigned by high-resolution NMR and the absolute configurations of anti-1 and anti-2 were determined by the exciton-chirality method. Optically active anti-2 can serve as a chiral host. It binds the HCl adduct of D-tryptophan methyl ester (D-TrpOMeHCl) 3.5 times stronger than the L-enantiomer (KD/KL=3.5).
Related Concept Videos
Chirality
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chirality in Nature
Prochirality
Molecules with Multiple Chiral Centers
Properties of Enantiomers and Optical Activity
Stereoisomerism of Cyclic Compounds

