title: A photochemical approach to aromatic extension of the corannulene nucleus.
abstract: A high yielding, general, and mild synthetic strategy is established for aromatic annulation of the corannulene scaffold. In this approach, a corannulene-based aldehyde, ylide, or ketone compound is conjugated with an aromatic unit of choice through a Wittig reaction. The resulting stilbene-like precursor can be subjected to a photochemically induced oxidative-cyclization process to yield a corannulene structure with an extended π-framework. The generality of synthesis allows for preparation of a wide range of polycyclic aromatic arene as well as heteroarene structures. Meanwhile, the mild nature of the developed protocol permits for incorporation of reactive and functional substituents onto the fused aromatic scaffold. Furthermore, efficient and simple synthesis ensures access to significant amounts of the material in a facile manner. In essence, this work demonstrates, for the first time, that photochemical synthesis is a highly practical alternative to the known flash vacuum pyrolysis and metal catalyzed processes for the aromatic extension of the bucky-bowl structure.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, School of Materials Science and Engineering, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore. mstuparu@ntu.edu.sg.
authors.forename: Venkatachalam
authors.initials: V
authors.lastname: Rajeshkumar
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, School of Materials Science and Engineering, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore. mstuparu@ntu.edu.sg.
authors.forename: Mihaiela C
authors.initials: MC
authors.lastname: Stuparu
mesh_terms: D055668:Photochemical Processes; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*
chemical_list: D011084:Polycyclic Aromatic Hydrocarbons; C434863:corannulene