Controlling the Reaction Steps of Bifunctional Molecules 1,5-Dibromo-2,6-dimethylnaphthalene on Different Substrates

Using scanning tunneling microscopy, We reveal that the methyl groups of 1,5-dibromo-2,6-dimethylzaplzthalene suppress Ullmann-twe intermolecular coupling on Au(111), Ag(111), and Cu(111) and steer the reactions yard different final products on the three substrates. On Au(111), the molecules feign ordered structures stabilized by intermolecular halogen bonds and desorb from the surface at above 420 K. On Ag(111), the molecules form halogen bonded structures but are converted into organornetallic structures at 3601 and desorb from the surface at above 600 K, On Cu(111), the molecules form organometallic structures at 300 K undergo an intermolecular cycloehydrogenation reaction at above 480 K. The reaction yields C-C bonds between debrominated carbons and methyl groups, resulting in dibenz[a,h] anthracene derivates and ultranarrow chiral-edge graphene nanoribbon motifs. This comparative snubs demonstrates a novel concept of using side groups to control the reaction steps that lead to specific; anal products on different substrates.