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Dresden 2014 – scientific programme

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O: Fachverband Oberflächenphysik

O 97: Organic/bio Molecules on Metal Surfaces IV

O 97.3: Talk

Friday, April 4, 2014, 11:00–11:15, TRE Phy

Surface-assisted synthesis of large hydrocarbon macrocycles: Honeycombenes and their organometallic intermediatesQitang Fan1, Cici Wang1, Yong Han1, Junfa Zhu1, Min Chen2, Hans-Jörg Drescher2, Malte Zugermeier2, Han Zhou2, Julian Kuttner2, Gerhard Hilt2, Wolfgang Hieringer3, and •J. Michael Gottfried21National Synchrotron Radiation Laboratory, University of Science and Technology of China — 2Fachbereich Chemie, Philipps-Universität Marburg, Germany — 3Lehrstuhl für Theoretische Chemie, Universität Erlangen-Nürnberg, Germany

Honeycombenes constitute a novel class of hexagonal hydrocarbon macrocycles, which are made by surface-assisted synthesis. The basic representative is [18]-honeycombene or hyperbenzene, a hexagon consisting of 18 phenyl rings.[1] The macrocycle was synthesized by surface-assisted Ullmann coupling of six 4,4''-dibromo-m-terphenyl (DBTP) precursor molecules on Cu(111). Hyperbenzene assembles to form close-packed islands with hexagonal symmetry. As intermediates of the surface Ullmann reaction, stable cyclic and linear organometallic species with C-Cu-C bonds have been observed. Their large diameters (2 nm for [18]-honeycombene) make the honeycombenes promising candidates for nanotroughs that could host metal and semiconductor particles or large organic molecules. [1] Q. Fan, C. Wang, Y. Han, J. Zhu, W. Hieringer, J. Kuttner, G. Hilt, J. M. Gottfried, Angew. Chem. Int. Ed. 52 (2013) 4668.

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