Clip[5]arenes: A new family of molecular clips. Issue 38 (19th September 2018)

• Record Type: Journal Article
• Authors: Shi, Bingbing; Li, Zhengtao; Liu, Yuezhou; Shangguan, Liqing; Zhu, Huangtianzhi; Ju, Huaqiang; Huang, Feihe
• Is Part Of: Tetrahedron letters. Volume 59:Issue 38(2018)
• Page Start: 3477
• Page End: 3480
• Publication Date: 2018-09-19
• Subjects: Supramolecular chemistry -- Molecular clips and tweezers -- Clip[5]arenes -- Host–guest recognition -- Pseudopolyrotaxane; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.08.019
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Clip[5]arenesC[5]OH andC[5]ME were synthesized and a pseudopolyrotaxane-like supramolecular structure was constructed by threadingC[5]OH onto a polyviologen polymer. Highlights: Clip[5]arenesC[5]OH andC[5]ME were obtained from Diels-Alder reactions. C[5]OH formed a strong inclusion complex with paraquat. AC[5]OH -based pseudopolyrotaxane-like supramolecular structure was constructed. Abstract: Here we report the design and syntheses of two new triptycene-based rigid acyclic C-shaped hosts, clip[5]arenesC[5]OH andC[5]ME, and the strong host–guest complexation betweenC[5]OH and an electron-poor bipyridinium salt, paraquatG . The K a value for the host–guest complexC[5]OH ⊃ G was calculated to be (1.09 ± 0.36) × 10 5 M −1 in acetone by using a non-linear curve-fitting method based on the UV–vis absorption titration experiments. Furthermore, based on this new host–guest recognition motif, a novel pseudopolyrotaxane-like supramolecular structure was constructed withC[5]OH threaded on polyviologen polymerVP-10 .