Hydrosolubilization of large aromatic molecules: Facile synthesis and characterization of water-soluble derivatives of decacyclene

Application of a mild-condition reductive/oxidative protocol to the large poorly-conjugated aromatic structure of decacyclene affords a water soluble oxygenated amphiphilic material which has been characterized and compared with the hydrocarbon precursor by means of solution (HNMR)-H-1 and solid-state C-13 CPMAS NMR, vibrational, electron, and mass spectroscopies. The nature of the different oxygenated moieties covalently attached to decacyclene framework is elucidated and the role of molecular O-2 in the oxidizing reaction path of reduced decacyclene is discussed.