Macrocyclic 2,7-Anthrylene Oligomers

Yuta Yamamoto; Kan Wakamatsu; Tetsuo Iwanaga; Hiroyasu Sato; Shinji Toyota

doi:10.1002/asia.201600230

Macrocyclic 2,7-Anthrylene Oligomers

Chem Asian J. 2016 May 6;11(9):1370-5. doi: 10.1002/asia.201600230. Epub 2016 Mar 24.

Authors

Yuta Yamamoto¹, Kan Wakamatsu¹, Tetsuo Iwanaga¹, Hiroyasu Sato², Shinji Toyota³

Affiliations

¹ Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama, 700-0005, Japan.
² X-ray Research Laboratory, Rigaku Corporation, 3-9-12 Matubaracho, Akishima, Tokyo, 196-8666, Japan.
³ Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8551, Japan. stoyota@cms.titech.ac.jp.

PMID: 26918910
DOI: 10.1002/asia.201600230

Abstract

A macrocyclic compound consisting of six 2,7-anthrylene units was successfully synthesized by Ni-mediated coupling of the corresponding dibromo precursor as a novel π-conjugated compound. This compound was sufficiently stable and soluble in organic solvents due to the presence of mesityl groups. X-ray analysis showed that the molecule had a nonplanar and hexagonal wheel-shaped framework of approximately S6 symmetry. The dynamic process between two S6 structures was observed by using the dynamic NMR technique, the barrier being 58 kJ mol(-1) . The spectroscopic properties of the hexamer were compared with those of analogous linear oligomers.

Keywords: NMR spectroscopy; arenes; conformation analysis; macrocycles; oligomerization.

Publication types

Research Support, Non-U.S. Gov't