Fluorinated [2]rotaxanes with spirofluorene motifs: a non-symmetric distribution of the ring component along the axle component. (13th December 2022)

• Record Type: Journal Article
• Authors: Rashid, Showkat; Murakami, Takashi; Koganezawa, Hiroshi; Yoshigoe, Yusuke; Hosoya, Shoichi; Saito, Shinichi
• Is Part Of: New journal of chemistry. Volume 47:Number 2(2023)
• Page Start: 900
• Page End: 909
• Publication Date: 2022-12-13
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj05021h
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The distribution of the ring component in [2]rotaxanes was modulated by the introduction of a less symmetric spiro ring. Abstract : Oxidative dimerization of terminal alkynes (Glaser coupling) triggered by spirofluorene derived macrocyclic phenanthroline–Cu complexes was implemented to synthesize a series of novel [2]rotaxanes. Size and structural variations among the components and their implications on the dynamic behaviour were investigated in detail through 1 H and 19 F NMR spectroscopy. Strong perturbations in the NMR spectra of the rotaxanes with substituted macrocyclic components with low symmetry indicated the non-symmetric distribution of the ring component along the axle component. In some [2]rotaxanes, localization of the ring component in the proximity of the 1, 3-diyne moiety was observed.