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carbo‐Naphthalene: A Polycyclic carbo‐Benzenoid Fragment of α‐Graphyne
Authors:Kévin Cocq  Nathalie Saffon‐Merceron  Yannick Coppel  Corentin Poidevin  Valérie Maraval  Remi Chauvin
Institution:1. CNRS, LCC (Laboratoire de Chimie de Coordination), Toulouse Cedex 4, France;2. Université de Toulouse, UPS, ICT-FR 2599, Toulouse Cedex 9, France;3. Université de Toulouse, UPS, Institut de Chimie de Toulouse ICT-FR-2599, Toulouse Cedex 9, France
Abstract:A ring carbo‐mer of naphthalene, C32Ar8 (Ar=pn‐pentylphenyl), has been obtained as a stable blue chromophore, after a 19‐step synthetic route involving methods inspired from those used in the synthesis of carbo‐benzenes, or specifically devised for the present target, like a double Sonogashira‐type coupling reaction. The last step is a SnCl2/HCl‐mediated reduction of a decaoxy‐carbo‐decalin, which is prepared through successive 8+10] macrocyclization steps. Two carbo‐benzene references are also described, C18Ar6 and o‐C18Ar4(C≡C‐SiiPr3)2. The carbo‐naphthalene bicycle is locally aromatic according to structural and magnetic criteria, as revealed by strong diatropic ring current effects on the deshielding of 1H nuclei of the Ar groups and on the negative value of the DFT‐calculated NICS at the center of the C18 rings (?12.8 ppm). The stability and aromaticity of this smallest fused molecular fragment of α‐graphyne allows prediction of the same properties for the carbon allotrope itself.
Keywords:aromaticity  carbocycles  density functional calculations  macrocycles  structure elucidation
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