Synfacts 2007(7): 0707-0707  
DOI: 10.1055/s-2007-968659
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Shape-Persistent Molecular Ladders

Contributor(s): Timothy M. Swager, Anne J. McNeil
C. S. Hartley, E. L. Elliott, J. S. Moore*
University of Illinois at Urbana-Champaign, USA
Further Information

Publication History

Publication Date:
22 June 2007 (online)

Significance

Moore and co-workers synthesized large, shape-persistent ladder molecules in one pot using dynamic covalent chemistry. The perfectly matched polycyclic molecule can be formed in high yields via reversible imine formation followed by irreversible reduction to the amine. High molecular weight byproducts were also observed and the yield of byproducts increased with increasing ‘n’. Although the precursor m-phenylene ethynylene oligomer syntheses can be laborious, Moore and co-workers utilized an efficient solid-phase synthetic approach (E. L. Elliott et al. J. Org. Chem. 2006, 71, 5282-5290).