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A Chiral Dicationic [8]Circulenoid: Photochemical Origin and Facile Thermal Conversion into a Helicene Congener


  • Financial support from the Czech Science Foundation (203/09/1614 and P207/10/2391 to F.T., 203/08/1428 to V.K., 203/09/0422 to P.S.*), and ASCR (RVO: 61388963) is gratefully acknowledged. P.S.* acknowledges support from the Czech Ministry of Education (Project No. ME08086) and I.C. (MSM0021620857). M.O. is a student of the International Max Planck Research School “Dynamical processes in Atoms, Molecules and Solids”. We thank Prof. P. Klán, L. Klíčová, Dr. D. Schröder, Dr. Á. Révész, J. Bařinková, and A. Šuláková for their very valuable help.


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Doubly positive: A circulene-like species has been transformed into its helical counterpart exclusively by the application of heat (see scheme). The synthesis of the chiral dicationic [8]circulenoid is based on a key [6+6] photocycloaddition and requires only five steps and no chromatographic purification.