Synfacts 2009(5): 0501-0501  
DOI: 10.1055/s-0029-1216562
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Non-Covalent Assembly of Enantiopure Nanocubes

Contributor(s): Timothy M. Swager, Jason R. Cox
J. Strübe, B. Neumann, H.-G. Stammler, D. Kuck*
Universität Bielefeld, Germany
Further Information

Publication History

Publication Date:
22 April 2009 (online)

Significance

In an effort to covalently assemble large concave frameworks through sequential condensation reactions of trisubstituted tribenzo­triquinacenes, the authors serendipitously fabricated a supramolecular nanocube. After nitration of 1, followed by bromination at the bridgehead carbons to give a mixture of 3a and 3b, the authors report enantiomerically pure single crystals of 3a from recrystallization in acetone. The nanocubes are primarily assembled through ”intercube" halogen contacts at the corners of the cubes. Residual electron density in the centers of the cubes suggests disordered solvent molecules at a ratio of 0.9 to 1.2 molecules per molecule of 3a as confirmed by NMR analysis.