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A Triply [5]Helicene-Bridged (1,3,5)Cyclophane |
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| Authors: | Dr. Frédéric Aribot Amélie Merle Dr. Pierre Dechambenoit Dr. Harald Bock Dr. Albert Artigas Dr. Nicolas Vanthuyne Dr. Yannick Carissan Dr. Denis Hagebaum-Reignier Dr. Yoann Coquerel Dr. Fabien Durola |
| Affiliation: | 1. Centre de Recherche Paul Pascal –, CNRS & Univ. Bordeaux, 115 Ave. du Dr. Schweitzer, 33600 Pessac, France;2. Aix Marseille Univ., CNRS, Centrale Marseille, iSm2, Marseille, France |
| Abstract: | A rigid propeller-shaped conjugated triple macrocycle consisting of two nearly perfectly stacked benzene rings and three linking [5]helicene moieties has been synthesized using a glyoxylic Perkin approach. Analysis of the electron delocalization in this atypical aromatic molecule revealed global aromaticity and a 78 π-electron circuit along the edge of its triple loop, to the detriment of the two 6 π-electron circuits in the two stacked benzene rings. |
| Keywords: | Aromaticity Cyclophane Helicene Macrocycle Perkin Reaction |