Synthesis of Interlocked and Non-Interlocked Deca(para-phenylene) Derivatives by Ni-mediated Biaryl Coupling

Misuzu Ohta; Ayano Okuda; Shoichi Hosoya; Yusuke Yoshigoe; Shinichi Saito

doi:10.1002/chem.202304309

Synthesis of Interlocked and Non-Interlocked Deca(para-phenylene) Derivatives by Ni-mediated Biaryl Coupling

Chemistry. 2024 Mar 15;30(16):e202304309. doi: 10.1002/chem.202304309. Epub 2024 Jan 26.

Authors

Misuzu Ohta¹, Ayano Okuda¹, Shoichi Hosoya², Yusuke Yoshigoe¹, Shinichi Saito¹

Affiliations

¹ Department of Chemistry, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku, Tokyo, Japan.
² Research Center for Medical and Dental Sciences, Tokyo Medical and Dental University, 1-5-45, Yushima, Bunkyo-ku, Tokyo, Japan.

PMID: 38199956
DOI: 10.1002/chem.202304309

Abstract

Oligo(para-phenylene) (PPn) is a compound composed of directly connected 1,4-phenylene moieties. The synthesis of PPn composed of six or more phenylene moieties with no substituent at the internal phenylene moiety has been challenging because of its low solubility. Herein we synthesized oligo(para-phenylene)[2]rotaxanes, including a deca(para-phenylene)[2]rotaxane, with a defined number of phenylene moieties. Biaryl coupling of iodoarenes mediated by macrocyclic dibenzodihydrophenanthroline-Ni complex was utilized for the first time to synthesize the [2]rotaxanes. Compared to the non-interlocked deca(para-phenylene), the deca(para-phenylene)[2]rotaxane showed higher solubility. The properties of the oligo(para-phenylene)[2]rotaxanes and non-interlocked oligo(para-phenylene)s were analyzed by spectroscopic methods.

Keywords: C−C coupling; nickel; oligo(para-phenylene); rotaxanes.

Abstract

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