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Synthesis and Self‐Assembly of Cyclic 2,7‐Anthrylene Ethynylene 1,3‐Phenylene Ethynylene Trimer with a Planar Conformation
Author(s) -
Takaki Yuta,
Ozawa Ryota,
Kajitani Takashi,
Fukushima Takanori,
Mitsui Masaaki,
Kobayashi Kenji
Publication year - 2016
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.201603627
Subject(s) - random hexamer , trimer , stacking , phenylene , equilateral triangle , crystallography , anthracene , planar , materials science , chemistry , polymer chemistry , dimer , photochemistry , organic chemistry , polymer , mathematics , geometry , computer graphics (images) , computer science
Cyclic arylene ethynylene hexamer 1 , composed of alternating 2,7‐anthrylene ethynylene units and meta ‐phenylene ethynylene units, was synthesized. It shows C 3 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 CDCl 3 at 303 K. Macrocycle 1 also self‐assembles into π‐stacked nanofibers in the drop‐cast film.