The balance between electronic and steric effects in the template-directed syntheses of [2]catenanes

Marta Pérez-Alvarez, Françisco M. Raymo, Stuart J. Rowan, David Schiraldi, J. Fraser Stoddart*, Zhen He Wang, Andrew J P White, David J. Williams

*この研究の対応する著者

研究成果: Article査読

16 被引用数 (Scopus)

抄録

Three bis-p-phenylene-34-crown-10 (BPP34C10) derivatives bearing ester groups on one or both of their two aromatic rings have been synthesized. These ester-substituted macrocyclic polyethers bind the paraquat dication in solution more strongly than BPP34C10. In contrast, however, acyclic analogs of these macrocyclic polyethers form much weaker complexes with cyclobis(paraquat-p-phenylene) (CBPQT4+). Likewise, catenane formation is diminished, in parallel with the number and disposition of the ester substituents on the hydroquinone rings of the macrocyclic polyethers. These observations suggest that complex and catenane formation are controlled by opposing recognition features, according to whether the ester-substituted hydroquinone rings assume either a guest or host role in 1:1 complexes with bipyridinium-based species, or lie inside or alongside the CBPQT4+ component in the[2]catenanes. Steric and electronic factors associated with the ester substituents probably account for the opposing trends in the inter-component recognition behavior.

本文言語English
ページ(範囲)3799-3808
ページ数10
ジャーナルTetrahedron
57
17
DOI
出版ステータスPublished - 2001 4月 23
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 有機化学
  • 創薬

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