Related Experiment Video
Updated: Jul 16, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Perylene bisimide atropisomers: synthesis, resolution, and stereochemical assignment
Peter Osswald1, Matthias Reichert, Gerhard Bringmann
1Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany.
Abstract:
The macrocyclization of the tetra-hydroxyphenoxy-substituted perylene bisimide 4 bearing two (R)-configured 2-octyl substituents in the imide positions by etherification with diethylene glycol ditosylate afforded both the diagonally bridged (1,7- and 6,12-linkage) and laterally bridged (1,12- and 6,7-linkage) regioisomers 6 and 7. The atropo-diastereomers of the diagonally bridged macrocycle 6 were separated by semipreparative HPLC on a chiral column, and their absolute configurations were determined by circular dichroism (CD) spectroscopy in combination with quantum chemical CD calculations. The isolated epimers (P,R,R)-6 and (M,R,R)-6 represent the first examples of diasteriomerically pure perylene bisimide atropisomers. The optical and chiroptical properties of these epimers were investigated by UV/vis, fluorescence, and CD spectroscopy, and their conformational properties have been explored by temperature-dependent 1H NMR studies.
Related Concept Videos
Prochirality
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Stereoisomers
Stereoisomerism of Cyclic Compounds
Polymer Classification: Stereospecificity
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

