Selective and effective rotation mode of copillar[5]arene by mono-functionalizing bulky substituent

Liu, Luzhi; Hua, Zhong-Ze; Duan, Wengui; Huang, Hong-Fei; Huang, Yan; Lin, Guo‐Qiang; Cen, Bo

doi:10.1016/j.tetlet.2016.05.085

Cited by 2 publications

(2 citation statements)

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“…Generally, in the formation of a pseudo[2]rotaxane by pillar[5]arene and a guest, the rotation of the phenolic units around the CH 2 bridge would be inhibited, resulting in less-shielded protons in the pillar[5]arene in the host–guest system [32]. Thus, the protons of the phenolic units were usually shifted downfield and the chemical shift change value (Δδ = δ complex − δ uncomplex ) could be used to evaluate the conformational characteristics of pillar[5]arenes.…”

Section: Resultsmentioning

confidence: 99%

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Recognition Selectivities of Lasso-Type Pseudo[1]rotaxane Based on a Mono-Ester-Functionalized Pillar[5]arene

et al. 2019

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Two types of mono-ester-functionalized pillar[5]arenes, P1 and P2, bearing different side-chain groups, were synthesized. Their host–guest complexation and self-inclusion properties were studied by 1H NMR and 2D nuclear overhauser effect spectroscopy (NOESY) NMR measurements. The results showed that the substituents on their phenolic units have a great influence on the self-assembly of both pillar[5]arenes, although they both could form stable pseudo[1]rotaxanes at room temperature. When eight bulky 4-brombutyloxy groups were capped on the cavity, instead of methoxy groups, pseudo[1]rotaxane P1 became less stable and its locked ester group in the inner space of cavity was not as deep as P2, leading to distinctly different host–guest properties between P1 and P2 with 1,6-dibromohexane. Moreover, pillar[5]arene P1 displayed effective molecular recognition toward 1,6-dichlorohexane and 1,2-bromoethane among the guest dihalides. In addition, the self-complex models and stabilities between P1 and P2 were also studied by computational modeling and experimental calculations.

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Section: Resultsmentioning

confidence: 99%

“…In our previous studies [30,31,32,33,34], we found that pillar[5]arene showed good binding properties to linear guests such as α,ω-dihaloalkane. Their complexation behavior with the guest (for instance, with 1,4-dibromobutane) was affected by the different substituents on the rings.…”

Section: Introductionmentioning

confidence: 99%