Synthesis and Self-Assembly of Cyclic 2,7-Anthrylene Ethynylene 1,3-Phenylene Ethynylene Trimer with a Planar Conformation

Yuta Takaki; Ryota Ozawa; Takashi Kajitani; Takanori Fukushima; Masaaki Mitsui; Kenji Kobayashi

doi:10.1002/chem.201603627

Synthesis and Self-Assembly of Cyclic 2,7-Anthrylene Ethynylene 1,3-Phenylene Ethynylene Trimer with a Planar Conformation

Chemistry. 2016 Nov 14;22(47):16760-16764. doi: 10.1002/chem.201603627. Epub 2016 Oct 13.

Authors

Yuta Takaki¹, Ryota Ozawa¹, Takashi Kajitani^{2

3}, Takanori Fukushima², Masaaki Mitsui⁴, Kenji Kobayashi¹

Affiliations

¹ Department of Chemistry, Faculty of Science, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.
² Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan.
³ RIKEN SPring-8 Center, 1-1-1 Kouto, Sayo, Hyogo, 679-5148, Japan.
⁴ Department of Chemistry, Graduate School of Science, Rikkyo University, 3-34-1 Nishiikebukuro, Toshima-ku, Tokyo, 171-8501, Japan.

PMID: 27734532
DOI: 10.1002/chem.201603627

Abstract

Cyclic arylene ethynylene hexamer 1, composed of alternating 2,7-anthrylene ethynylene units and meta-phenylene ethynylene units, was synthesized. It shows C₃ symmetry and possesses a flat and rigid conformation with a large equilateral triangle-like cavity. Macrocycle 1 self-associates through π-π stacking interactions between the anthracene-containing macrocyclic aromatic cores with indefinite-association constant K_E =6980 m^-1 in CDCl₃ at 303 K. Macrocycle 1 also self-assembles into π-stacked nanofibers in the drop-cast film.

Keywords: anthracene; arenes; macrocycles; self-assembly; supramolecular chemistry.