A Facile Route to New and Old Cyclophanes from a Pnictogen-activated Self-Assembly Reaction


The well-defined topology and high strain of cyclophanes has found utility in a number of applications including asymmetric catalysis, insulating plastics, and organic electronics.  Unfortunately, the field of cyclophane chemistry has been hindered by a lack of high yielding and functional group tolerant preparative methods for their synthesis.  

University of Oregon’s inventors have developed a selective, high yielding alternative to traditional cyclophane synthesis by the use of a pnictogen additive to direct the self-assembly of discrete disulfide cyclophanes.  Using this approach eliminates the need for caustic, temperature-sensitive methods and allows for the synthesis of formerly inaccessible, higher order species such as trimers, tetramers, pentamers, hexamers, and tetrahedra.  This method has wide functional group tolerance. This approach will be exceptionally useful in the synthetic design of many heterocycles like calixarenes, cryptands, and spherands and in ring-opening metathesis polymerization to make conjugated polymers.

The University of Oregon is interested in finding industrial partners who want to integrate this method in to their cyclophane synthetic processes.

Patents: US9,790,192 & US10,344,005 (UO-14-55)

Patent Information:
For Information, Contact:
Jim Deane
University of Oregon
Darren Johnson
Mary Collins
Matthew Carnes