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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
Author(s) -
Tsuya Takuya,
Iritani Kohei,
Tahara Kazukuni,
Tobe Yoshito,
Iwanaga Tetsuo,
Toyota Shinji
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405638
Subject(s) - alkyl , anthracene , chemistry , molecule , chirality (physics) , monolayer , acetylene , dimer , crystallography , intermolecular force , stereochemistry , polymer chemistry , photochemistry , organic chemistry , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.