A Triply [5]Helicene‐Bridged (1,3,5)Cyclophane
Frédéric Aribot, A.M. Merle, Pierre Dechambenoit, Harald Böck, Albert Artigas, Nicolas Vanthuyne, Yannick Carissan, Denis Hagebaum‐Reignier, Yoann Coquerel, Fabien Durola
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.
Topics & Concepts
HeliceneAromaticityElectron delocalizationCyclophaneDelocalized electronBenzeneMoleculeChemistryConjugated systemStackingAntiaromaticityCrystallographyStereochemistryOrganic chemistryPolymerSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryFullerene Chemistry and Applications