Synthesis and characterization of cationic iodonium macrocycles.
A synthetic strategy for the high-yield preparation of iodonium containing macrocycles such as rhomboids, a square, and a pentagon is described, with the long-term objective of preparing iodonium compounds for potential molecular electronics applications. Two cationic rhomboid shaped molecules were prepared for the first time (55-70%) by the treatment of compounds 11 and 12a or 12b with Me3SiOTf. The reaction of dication 8 with 6 in the presence of Me3SiOTf gave an iodonium containing molecular square in 70% yield. In addition, a pentagon-shaped macromolecule was prepared in 60% yield. These iodonium-containing charged macromolecules were characterized by multinuclear NMR, mass spectrometry, and physical means.
Radhakrishnan
Ukkiramapandian
U
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
Stang
Peter J
PJ
D002412:Cations / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009861:Onium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
D002412:Cations; D009861:Onium Compounds