Related Experiment Video
Updated: Jan 9, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Serendipitous Assembly of Chiral Face-Rotating Molecular Boxes Directed by Non-Covalent Templation
Mingyu Cui1, Xue Dong1, Guoqiang Jiang1
1Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM) and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China.
Abstract:
A serendipitous outcome in the mandelic acid-mediated imine condensation of a tetraphenylethene-derived tetraaldehyde and tris(2-aminoethyl)amine led to [2 + 4] face-rotating molecular boxes, rather than the expected [6 + 8] cubic cages. The resulting D2-symmetric assemblies feature two homochiral tetraphenylethene facial units and four unreacted amine handles. Mandelic acid engages in cooperative hydrogen bonding, steric effect and C-H···π interactions that steer the assembly pathway and supramolecular chirality. NMR, ECD, and X-ray analyses confirm the formation of a pair of diastereomeric supramolecular complexes exhibiting distinct optical activity in solution.
Related Concept Videos
Prochirality
Molecules with Multiple Chiral Centers
Chirality in Nature
Fischer Projections
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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...

