Molecular folding of C60 acetylenic cyclophanes: pi-stacking of superimposed aromatic rings.
[structure: see text] The syntheses of two distinct families of phenylyne helical cyclophanes with potential for organic materials are described. The meta-bonded atropisomers afford interesting bowtie-like and butterfly-like conformers from a palladium(0), copper-mediated coupling sequence. Molecular modeling revealed the contrasting stereochemistry in these systems from differential molecular folding pathways during cyclization. The interplanar separation of the superimposed aromatic rings is approximately 3.5 A.
Heuft
Matthew A
MA
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Collins
Shawn K
SK
Fallis
Alex G
AG