Oberflächengestützte Synthese von Hyperbenzol‐Nanogehegen

On‐Surface Reactions

“…Additionally, the reaction of 1,3‐diiodobenzene allowed for the formation of sexiphenylene macrocycles. A similar approach has been used by Fan et al By enlarging the reactant by two meta ‐positioned phenyl rings, that is, changing from 1,4‐dihalobenzene to 4,4′′‐dihalo‐m‐terphenyl, they were able to synthesize hexagonally arranged hyperbenzene macrocycles on a Cu(111) surface 15. Similarly, the synthesis of poly(3,4‐ethylenedioxythiophene) by polymerization of 2,5‐diiodo‐3,4‐ethylenedioxythiophene on Cu(110) has been shown 16.…”

Dehydrogenative Homocoupling of Alkyl Chains on Cu(110)

“…In this respect, dehydrogenative or dehalogenated homocoupling of reactants with C−H or C−X (X=halogen) groups has proven a feasible route . Among these on‐surface reactions, Ullmann coupling has been the most extensively studied for constructing aromatic molecular structures . In addition, debrominated homocoupling of terminal alkanes, that is, the on‐surface Wurtz reaction, was also reported by our group very recently .…”

“…Recently, the construction of nanostructures through covalent interlinking of molecular building blocks on metal surfaces has been among the most active areas of surface science research . Various chemical reactions have been employed on surfaces, including, for example, the Ullmann reaction, Bergman cyclization, decarboxylative polymerization, azide–alkyne click reaction, Glaser coupling, imine formation, and dimerization of N‐heterocyclic carbenes . In particular, on‐surface synthesis involving hydrocarbons has aroused particular attention due to interest in fabricating novel carbon nanostructures and nanomaterials.…”

Theoretical Modeling of the Surface‐Guided Self‐Assembly of Functional Molecules

“…Moreover, we can also observe “phase separation” producing the R ‐domains embedded in a pool of randomly distributed cyclic hexamers. A similar progression of adsorbed phases has been observed experimentally in the on‐surface synthesis of macrocycles comprising the achiral dibromo‐terphenyl building blocks . Interestingly, analogous effect does not occur in the case of the racemic overlayer depicted in the right panel of the figure.…”

“…The observed chiral resolution of the conformers produced molecular aggregates, which when desorbed, become not distinguishable and thus are one chemical product. In fact, the described process resembles the on‐surface synthesis of hyperbenzene in which bent halogenated terphenyl molecules have been used as monomers . The experimental results reported therein by Fan and coworkers revealed the formation of hexagonal oligomers (hyperbenzene) comprising the achiral terphenyl units.…”