Synthesis and Properties of a Cyclohexa‐2, 7‐anthrylene Ethynylene Derivative. (3rd November 2020)

• Record Type: Journal Article
• Authors: Matsuki, Hironori; Okubo, Keisuke; Takaki, Yuta; Niihori, Yoshiki; Mitsui, Masaaki; Kayahara, Eiichi; Yamago, Shigeru; Kobayashi, Kenji
• Is Part Of: Angewandte Chemie. Volume 133:Number 2(2021)
• Page Start: 1011
• Page End: 1016
• Publication Date: 2020-11-03
• Subjects: arenes -- conjugation -- host–guest systems -- macrocycles -- π interactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202012120
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : The synthesis of a cyclohexa‐2, 7‐anthrylene ethynylene derivative was achieved for the first time. This macrocycle possesses a planar conformation and an inner cavity that includes [9]cycloparaphenylene through an aromatic edge‐to‐face CH‐π interaction.