Rotaxanes comprising cyclic phenylenedioxydiacetamides and secondary mono- and bis-dialkylammonium ions: effect of macrocyclic ring size on pseudorotaxane formation

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Author: Nakamura, Takanoriほか

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Publication date: 2020-01-06

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Note (General)：: In this study we synthesized three macrocyclic tetralactams 1, possessing two phenylenedioxydiacetamide units and various spacers, for use as hydrogen...

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Material Type: 文書・図像類
Title: Rotaxanes comprising cyclic phenylenedioxydiacetamides and secondary mono- and bis-dialkylammonium ions: effect of macrocyclic ring size on pseudorotaxane formation
Author/Editor: Nakamura, Takanori
Mori, Yuka
Naito, Masaya
Okuma, Yukari
Miyagawa, Shinobu
Takaya, Hikaru
Kawasaki, Tsuneomi
Tokunaga, Yuji
Author Heading: Nakamura, Takanori
Mori, Yuka
Naito, Masaya
Okuma, Yukari
Miyagawa, Shinobu
Takaya, Hikaru
Kawasaki, Tsuneomi
Tokunaga, Yuji
Publication Date: 2020-01-06
Publication Date (W3CDTF): 2020-01-06
Alternative Title: Rotaxanes comprising cyclic phenylenedioxydiacetamides and secondary mono- and bis-dialkylammonium ions: effect of macrocyclic ring size on pseudorotaxane formation
Periodical title: Organic Chemistry Frontiers
No. or year of volume/issue: 7 3
Volume: 7
Issue: 3
Pages: 513-524
ISSN (Periodical Title): ISSN : 2052-4129
Text Language Code: eng
Target Audience: 一般
Note (General): In this study we synthesized three macrocyclic tetralactams 1, possessing two phenylenedioxydiacetamide units and various spacers, for use as hydrogen bond accepting hosts for mono- and bis-dialkylammonium ions. The cyclic tetralactam 1b, featuring propylene spacers, bound secondary mono- and bis-dialkylammonium ions efficiently to form corresponding pseudo[2]rotaxanes stabilized through hydrogen bonding between the two components. The cyclic tetralactams bearing other spacers (1a and 1d) also bound these dialkylammonium ions, but the macrocycle 1a (ethylene spacer) predominantly constructed a face-to-face complex, while the macrocycle 1d (3-oxypentalene spacer) formed a non-selective complex. We synthesized three [2]rotaxanes, through imine and oxime formation, from pseudo[2]rotaxanes self-assembled from the propylene-spacer tetralactam 1b and mono- and bis-alkylammonium ions. 1H NMR spectroscopy and X-ray crystallography revealed that hydrogen bonds between the dumbbell-shaped and macrocyclic components restricted the conformation of the amide units in the [2]rotaxanes in solution and in the solid state.
Access Restrictions: 限定公開
Rights (production): This journal is copyright the Partner Organisations 2020
Related Material (DOI): 10.1039/C9QO01359H
Data Provider (Database): 国立情報学研究所 : 学術機関リポジトリデータベース（IRDB）（機関リポジトリ）
https://irdb.nii.ac.jp
Original Data Provider (Database): 福井大学 : 福井大学学術機関リポジトリ