Synfacts 2015; 11(2): 0150
DOI: 10.1055/s-0034-1379834
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

12 nm Soluble Wheel from c. 1878

Timothy M. Swager
Sarah P. Luppino
May R, Jester S.-S, * Höger S. * Rheinische Friedrich-Wilhelms-Universität Bonn, Germany
A Giant Molecular Spoked Wheel.

J. Am. Chem. Soc. 2014;
136: 16732-16735
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19. Januar 2015 (online)



The authors have designed and synthesized a soluble and highly rigid macromolecular wheel of the sum formula C1878H2682. The six ‘spokes’ of the hexagonal wheel are assembled, joined to the central hexaphenylbenzene unit, and cyclized via palladium coupling in a convergent and modular fashion.



The spokes maintain shape-persistence and further solubilize the rigid molecule with numerous dodecyl side chains. The yields in the synthetic sequence vary from modest (49%) to excellent (98%). The isolated product is a yellow fluorescent solid.