Hydrosolubilization of Large Aromatic Molecules: Facile Synthesis and Characterization of Water-Soluble Derivatives of Decacyclene

Abstract

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 1 H NMR and solid-state 13 C 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.