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Synthesis and Properties of a Cyclohexa‐2,7‐anthrylene Ethynylene Derivative
Author(s) -
Matsuki Hironori,
Okubo Keisuke,
Takaki Yuta,
Niihori Yoshiki,
Mitsui Masaaki,
Kayahara Eiichi,
Yamago Shigeru,
Kobayashi Kenji
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202012120
Subject(s) - chemistry , stacking , anthracene , monomer , linker , derivative (finance) , stereochemistry , crystallography , photochemistry , organic chemistry , polymer , computer science , financial economics , economics , operating system
The synthesis of a cyclohexa‐2,7‐(4,5‐diaryl)anthrylene ethynylene ( 1 ) was achieved for the first time by using 1,8‐diaryl‐3,6‐diborylanthracene and 1,8‐diaryl‐3,6‐diiodoanthracene as key synthetic intermediates. Macrocycle 1 possesses a planar conformation of approximately D 6 h symmetry, because of the triple‐bond linker between the anthracene units at the 2,7‐positions. It was confirmed that macrocycle 1 , bearing bulky substituents at the outer peripheral positions, behaves as a monomeric form in solution without π‐stacking self‐association. Macrocycle 1 has an inner‐cavity size that allows specific inclusion of [9]cycloparaphenylene ([9]CPP), but not [8]CPP or [10]CPP, through an aromatic edge‐to‐face CH‐π interaction.