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Ferrocene-containing [1]-, [2]-, [3]- and [4]rotaxanes synthesized from a common precursor

RSC Advances, ISSN: 2046-2069, Vol: 6, Issue: 47, Page: 41369-41375
2016
  • 13
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  • Citations
    13
    • Citation Indexes
      13
  • Captures
    10

Article Description

The Cu-catalyzed reaction of a dialkylammonium, having ferrocenyl and hexynyl end groups, FcCHNHCHCH-4-O(CH)CCH]PF (Fc = Fe(CH)(CH)), with a crown ether having an azidemethyl side-arm yields a [1]rotaxane composed of a single molecule. The crystal structure of the [1]rotaxane suggests an arrangement where the 1,4-phenylene ring is tilted at 22° close to the catechol ring rather than in a parallel alignment. Another dialkylammonium with ferrocenyl and alkynyl terminal groups, [FcCHNHCHCH-4-O(CH)CCH]PF, reacts with aromatic compounds with one to three azide groups in the presence of dibenzo[24]crown-8-ether (DB24C8) and [Cu(MeCN)]PF catalyst, to afford the corresponding [2]-[4]rotaxanes. The products contain DB24C8 molecules as the cyclic components which are bound to the ammonium group of the axle component with NH⋯O hydrogen bonding. The [3]rotaxane having two triazole groups on the axle component reacts with PdCl(MeCN) to yield mono- and di-palladium complexes with different conformations of the axle component.

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