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Updated: Dec 30, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Planar Anthracene-Acetylene Frameworks as a Stereogenic Motif
Shinji Toyota1, Hiroshi Ikeda1,2, Tetsuo Iwanaga3
1Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.
Abstract:
Planar and rigid frameworks that consist of two 1,8-substituted anthracene units and two acetylene linkers were utilized as key structures for the generation of stereoisomers through the introduction of extra substituents. These compounds were synthesized from 1,8-substituted anthracene building units by a combination of coupling reactions. We designed diastereomers, enantiomers, and topomers by modifying the combination of the two linkers and the number of substituents at sterically crowded intraannular positions. The molecular structures, stereochemistry, and properties of these compounds were investigated by means of spectroscopic techniques and theoretical calculations. A prochiral cyclic dimer with one extraannular substituent was designed to generate a stereochemical phenomenon in two dimensions. Scanning tunneling microscopy measurements revealed that the molecules formed a self-assembled monolayer at the liquid-solid interface in a conglomerate-type manner. The scope and potential of the macrocyclic frameworks in studies of π-conjugated compounds are presented.
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