155259-17-9Relevant articles and documents
Redox-switchable intramolecular π-π-stacking of perylene bisimide dyes in a cyclophane
Schlosser, Felix,Moos, Michael,Lambert, Christoph,Wuerthner, Frank
, p. 410 - 414 (2013/03/13)
Molecular actuation by stepwise electrochemical reduction is demonstrated for a cyclophane that exhibits a pronounced conformational transition from a closed cavity with cofacially stacked PBIs in the neutral state to an expanded open cavity in the three- and fourfold reduced state. Copyright
Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynylbenzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer
Zhou, Qin,Carroll, Patrick J.,Swager, Timothy M.
, p. 1294 - 1301 (2007/10/02)
Diacetylene macrocycles 2-4 (n=1-3) (R=H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives.These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers.The reported results indicate that when the R groups are large the dimeric macrocycle (n=1) can be prepared in as high as 74percent yield from the corresponding 1,2-diethynylbenzene in a one-step procedure.An alternate multistep procedure was found to produce the tetrameric macrocycle (n=3,R=C6H13) in 45percent yield.The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive.The dimers undergo a rapid very exothermic polymerization at 100-125 deg C, indicative of a chain reaction.Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20? electron tetraiodide fused ring system.Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.
