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Chemistry of Anthracene–Acetylene Oligomers XXV: On‐Surface Chirality of a Self‐Assembled Molecular Network of a Fan‐Blade‐Shaped Anthracene–Acetylene Macrocycle with a Long Alkyl Chain
Authors:Dr. Takuya Tsuya  Kohei Iritani  Dr. Kazukuni Tahara  Prof. Yoshito Tobe  Dr. Tetsuo Iwanaga  Prof. Shinji Toyota
Affiliation:1. Department of Chemistry, Faculty of Science, Okayama University of Science, 1‐1 Ridaicho, Kita‐ku, Okayama 700‐0005 (Japan);2. Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560‐8531 (Japan)
Abstract:An anthracene cyclic dimer with two different linkers and a dodecyl group was synthesized by means of coupling reactions. The calculated structure had a planar macrocyclic π core and a linear alkyl chain. Scanning tunneling microscopy observations at the 1‐phenyloctane/graphite interface revealed that the molecules formed a self‐assembled monolayer that consisted of linear striped bright and dark bands. In each domain, the molecular network consisted of either Re or Si molecules that differed in the two‐dimensional chirality about the macrocyclic faces, which led to a unique conglomerate‐type self‐assembly. The molecular packing mode and the conformation of the alkyl chains are discussed in terms of the intermolecular interactions and the interactions between the molecules and the graphite surface with the aid of MM3 simulations of a model system.
Keywords:chirality  molecular modeling  oligomers  scanning probe microscopy  self‐assembly
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