“Rim‐Differentiated” Pillar[6]arenes

Yang, Chao; Thikekar, Tushar Ulhas; Fang, Wangjian; Chang, Rong; Xu, Jiong; Ouyang, Nianfeng; Xu, Jun; Gao, Yan; Guo, Minjie; Zuilhof, Han; Sue, Andrew C.-H.

doi:10.1002/ange.202204589

Cited by 7 publications

(2 citation statements)

References 151 publications

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“…The ion-pair recognition of silver(I) trifluoroacetate for a peralkylated pillar[5]arene was reported by the Huang group . Recently, a dimeric silver(I) trifluoroacetate template was used to synthesize a rim-differentiated pillar[6]arene by the Sue group . Nevertheless, coordination networks incorporating pillararenes with entangled structures are almost an unexplored area so far …”

Section: Introductionmentioning

confidence: 99%

“…58 Recently, a dimeric silver(I) trifluoroacetate template was used to synthesize a rim-differentiated pillar [6]arene by the Sue group. 59 Nevertheless, coordination networks incorporating pillararenes with entangled structures are almost an unexplored area so far. 11 In the present work, as depicted schematically in Figure 2, the combination of the di-armed pillar [5]arene L and silver(I) trifluoroacetate leads to the formation of a poly-pseudorotaxane 2 and represents the first example in which the same salt-type guest component is used to both thread and link the poly-pseudo-rotaxane product.…”

Section: ■ Introductionmentioning

confidence: 99%

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Solvent-Dependent Self-Assembly of a Pillar[5]arene-Based Poly-Pseudo-Rotaxane Linked and Threaded by Silver(I) Trifluoroacetate: A Double Role

Kim

Park

et al. 2023

Inorg. Chem.

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In the supramolecule area, the fabrication of a new concept called polyrotaxanes or poly-pseudo-rotaxanes remains challenging. We herein report the formation of a poly-pseudo-rotaxane in which the same salt-type guest serves both linking and threading in the resulting structure. The combination of A1/A2-thiopyridyl pillar[5]arene (L) and silver(I) trifluoroacetate in CHCl 3 /CH 3 OH afforded a one-dimensional (1D) poly-pseudo-rotaxane. In this structure, to our surprise, the AgCF 3 CO 2 guest not only links the di-armed L ligands via an infinite −L−Ag−L−Ag− arrangement but also threads into a pillar[5]arene cavity in a dimer form, (AgCF 3 CO 2 ) 2 . In contrast, the same reaction in CH 2 Cl 2 /CH 3 OH yielded a simple 1D coordination polymer because an included CH 2 Cl 2 molecule in the pillar[5]arene cavity prevents the threading of the silver(I) trifluoroacetate guest. Comparative 1 Hand 19 F-NMR studies support the solvent-dependent poly-pseudo-rotaxane formation at a lower concentration of L.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Solvent-Dependent Self-Assembly of a Pillar[5]arene-Based Poly-Pseudo-Rotaxane Linked and Threaded by Silver(I) Trifluoroacetate: A Double Role

Kim

Park

et al. 2023

Inorg. Chem.

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Modulating Supramolecular Charge‐Transfer Interactions in the Solid State using Compressible Macrocyclic Hosts

et al. 2022

Angewandte Chemie

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Modulating intermolecular charge‐transfer (ICT) interactions between specific donor and acceptor species in host–guest systems is a big challenge and full of research value in supramolecular chemistry and materials science. In this work, a strategy to modulate the supramolecular ICT interactions in the solid state is developed by compressing the binding cavity of a macrocyclic host named perethylated leaning pillar[6]arene (p‐EtLP6). The solid‐state ICT affinities of p‐EtLP6 toward multi‐types of electron‐deficient planar guests could be significantly enhanced by transforming the macrocyclic backbone from the original para‐bridged mode into a hybrid para‐ and meta‐bridged isomeric form (m‐EtLP6). X‐ray single‐crystal structural analyses incorporating theoretical calculation demonstrate that the improved ICT affinities are mainly attributed to the superior host–guest size fit arising from the compressed binding cavity in m‐EtLP6 as compared with p‐EtLP6.

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Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene‐Bridged Naphthotubes

et al. 2022

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Macrocyclic hosts with a well-defined cavity are particularly appealing for supramolecular chemistry, but they are still rare. In this research, we reported a new class of macrocyclic hosts, namely methylenebridged naphthotubes, with well-defined cavities. They were synthesized through TFA-catalyzed Friedel-Crafts reactions between alkoxy-substituted bisnaphthalenes and paraformaldehyde. A configurational selection was observed. Three-membered macrocycles possess a single cavity, while four-membered macrocycles adopt a double-cavity conformation or a self-filling conformation depending on the alkoxy length. The small homologue shows quite strong binding affinities (up to 10 8 M À 1 ) to organic cations, which is better than structurally similar but flexible macrocycles. This demonstrates the advantage of a well-defined cavity in molecular recognition. Moreover, these naphthotubes can be used as chirality sensors for chiral organic cations through different chirality transfer mechanisms.

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“Rim‐Differentiated” Pillar[6]arenes

Cited by 7 publications

References 151 publications

Solvent-Dependent Self-Assembly of a Pillar[5]arene-Based Poly-Pseudo-Rotaxane Linked and Threaded by Silver(I) Trifluoroacetate: A Double Role

Solvent-Dependent Self-Assembly of a Pillar[5]arene-Based Poly-Pseudo-Rotaxane Linked and Threaded by Silver(I) Trifluoroacetate: A Double Role

Modulating Supramolecular Charge‐Transfer Interactions in the Solid State using Compressible Macrocyclic Hosts

Synthesis, Configurational Analysis, Molecular Recognition and Chirality Sensing of Methylene‐Bridged Naphthotubes

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