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| - Carbon Networks Based on Dehydrobenzoannulenes. 4. Synthesisof “Star” and “Trefoil” Graphdiyne Substructures via SixfoldCross-Coupling of Hexaiodobenzene
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| - The synthesis and characterization of star- and trefoil-shaped polyethynyl aromatic structures,which represent model substructures of the all-carbon network graphdiyne, are described. Assemblyof these macrocycles is accomplished via 6-fold Sonogashira cross-coupling of hexaiodobenzene usingPd[P(o-Tol)3]2 and CuI as the catalytic system. The development of these modified Sonogashiraconditions is detailed. This work has led to the synthesis of a new family of hexakis(phenylbutadiynyl)benzene derivatives (4a−c), the largest of which is the D3h-symmetric “trefoil” 2 and iscomposed of three [18]annulenes fused at a common benzene ring. Attempts at the synthesis of“wheel” 3 are also described. Compound 2 represents the largest fragment of the graphdiyne networkto date. UV−vis spectroscopic studies indicate enhanced electron delocalization throughout theextended π-system.
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