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O: Fachverband Oberflächenphysik

O 36: Posters: Bio/organic Molecules on Surfaces, Graphene, Solid/liquid interfaces, Metal Substrates, Electronic Structure Theory

O 36.32: Poster

Dienstag, 1. April 2014, 18:30–22:00, P1

Honeycombenes: A novel class of hydrocarbon macrocycles made by surface-assisted synthesis — •Min Chen¹, Jian Shang², Yongfeng Wang², Kai Wu², Qitang Fan³, Cici Wang³, Yong Han³, Junfa Zhu³, Julian Kuttner¹, Gerhard Hilt¹, and J.Michael Gottfried¹ — ¹Fachbereich Chemie, Philipps-Universität Marburg, Germany — ²College of Chemistry and Molecular Engineering, Peking University, China — ³National Synchrotron Radiation Laboratory, University of Science and Technology of China, China

Surface-assisted synthesis provides an elegant route to molecules that cannot be synthesized in solution or that are too large for vapor-deposition. Both factors apply for [n]-honeycombenes, a novel class of planar hydrocarbon macrocycles of hexagonal geometry. [18]-Honeycombene or hyperbenzene (C₁₀₈H₇₂) consists of 18 phenyl rings and was made by surface-assisted Ullmann reaction from 4,4^′′-dibromo-m-terphenyl (DBTP) on Cu(111). The molecules arrange in long-range ordered islands with hexagonal unit cell. [30]-Honeycombene (C₁₈₀H₁₂₀), a hexagon with 30 phenyl rings, was made on Ag(111) from 4,4^′′′′-dibromo-m-quinquephenyl (DBQP). DBQP gives also access to strained rings of heptagonal (C₂₁₀H₁₄₀), pentagonal (C₁₅₀H₁₀₀) and square (C₁₂₀H₈₀) shape. Using STS, the electronic structure along the ring perimeter and the confinement of surface state electrons trapped inside the macrocycles were studied. The large diameters of >2 nm and >3.5 nm make [18]- and [30]-honeycombene promising candidates for nanotroughs that can host other molecules or nanoparticles.