Synthetic Evolution of the Multifarene Cavity from Planar Predecessors

Chinna Ayya Swamy P, Ephrath Solel, Ofer Reany, Ehud Keinan

Research output: Contribution to journalArticlepeer-review


The stepwise evolution of curved multifarene structures from planar precursors is demonstrated, highlighting three architectural design elements: 1) employment of various aromatic units, 2) changing the hybridization of the linking atoms from sp2 to sp3, and 3) rigidification of the system by the introduction of five-membered rings. Similar design elements have been employed to transform graphene sheets into curved carbon structures. Specifically, the stepwise synthetic evolution of multifarene[2+2], which has a curved, quite rigid structure, begins with a planar, tetraimine precursor, conversion to pairs of vicinal diamines, and the transformation of these pairs to cyclic thiourea groups. This process was probed by NMR spectroscopy and X-ray crystallography. Since varying the carbonylation conditions resulted in carbamates or thiocarbamates rather than the urea or thiourea isomers, the isomeric interconversion was studied both experimentally and by DFT computations. The carbamate versus urea preference was found to reflect either kinetic or thermodynamic control, respectively.

Original languageEnglish
Pages (from-to)15319-15328
Number of pages10
JournalChemistry - A European Journal
Issue number57
StatePublished - 12 Oct 2018

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


  • carbamates
  • cavitands
  • molecular design
  • multifarenes
  • supramolecular chemistry


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