Tubularenes |
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Authors: | Saber Mirzaei,Edison Castro,Raú l Herná ndez Sá nchez |
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Affiliation: | Department of Chemistry, University of Pittsburgh, 219 Parkman Ave., Pittsburgh Pennsylvania 15260 USA, |
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Abstract: | We report the synthesis and characterization of conjugated, conformationally rigid, and electroactive carbon-based nanotubes that we term tubularenes. These structures are constructed from a resorcin[nb]arene base. Cyclization of the conjugated aromatic nanotube is achieved in one-pot eight-fold C–C bond formation via Suzuki–Miyaura cross-coupling. DFT calculations indicate a buildup of strain energy in excess of 90 kcal mol−1. The resulting architectures contain large internal void spaces >260 Å3, are fluorescent, and able to accept up to 4 electrons. This represents the first scaffolding approach that provides conjugated nanotube architectures.First scaffolding approach to obtain tubular-shaped contorted aromatic architectures. |
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