Synthesis and characterization of a new pillar[5]arene-based [1]rotaxane

Tian, Huasheng; Wang, Qianqian; Lin, Po‐Han; Meguellati, Kamel

doi:10.1016/j.tetlet.2018.08.004

Cited by 13 publications

(5 citation statements)

References 45 publications

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“…These signals were found to split into two sets of peaks (H a′ and H b′ ), which are attributed to the inclusion of some of the suberate anion into to cavity of pillar [5]arene core of 1 as further supported by the emergence of two new peaks at −0.34 and −2.53 ppm (Figure S4) upon inclusion of suberate into the cavity of pillar [5]arene core. 42,43 These peaks are due to the inner methylene peaks of suberate anion and the inclusion is more pronounced when CD 2 Cl 2 was used as a solvent. As can be seen in Figure S4, neither inner methylene peak upfield shifts nor the splitting of H a and H b resonance signals were observed when CD 2 Cl 2 was used as a solvent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cross-Linked Supramolecular Polymer Based on Calix[4]pyrrole-Decorated Pillar[5]arene and Its Application in Micropollutant Removal

Ünlü,

Aydogan

2023

ACS Appl. Polym. Mater.

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A calix[4]pyrrole-decorated pillar[5]arene was synthesized via azide-alkyne “click” chemistry and used to prepare a cross-linked supramolecular polymer in chloroform based on the anion recognition ability of calix[4]pyrrole. Complexation experiments revealed that while one of the cross-linkers, terephthalate anion, was not able to form strong complexation, suberate anion was found to act as a suitable cross-linker. Supramolecular polymerization and performance of monomers were monitored with a combination of techniques including 1H-, diffusion-ordered 1H NMR spectroscopy experiments, viscosity, and SEM analyses. Thermo and competing anion responsiveness of the cross-linked supramolecular polymer were also shown by means of 1H-NMR analyses and viscosity measurements. Micropollutant removal ability of the cross-linked supramolecular polymer in solid and gel forms was also investigated by using methylene blue, methyl violet 2B, and rhodamine B as surrogate pollutants, and UV/Vis experiments revealed that while the solid form of the supramolecular polymer performs better in the case of methylene blue and methyl violet, its gel form provides slightly better removal efficiency for rhodamine B.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Cross-Linked Supramolecular Polymer Based on Calix[4]pyrrole-Decorated Pillar[5]arene and Its Application in Micropollutant Removal

Ünlü,

Aydogan

2023

ACS Appl. Polym. Mater.

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“…Terminal amines were capped through condensation with aryl aldehydes ( P22, P23 ) 114,115 and carboxylic acids ( P24, P25 ), 116,117 S N 2 reaction with an alkyl bromide ( P26 ), 118 reacting with isothiocyanates ( P27 ), 119 and their combination ( P28 ). 120 When the linker units in condensation-based capping schemes were shorter than propylene diamine, 114–116 the side chains did not complex with pillar[5]arene cores, but existed in free states. When the threading units had sufficient length, many types of [1]rotaxane-type SCM were obtained, as confirmed by NMR spectroscopy and X-ray crystallography.…”

Section: Single-component Mechanically Self-complexed Molecules and R...mentioning

confidence: 99%

Noncovalently bound and mechanically interlocked systems using pillar[n]arenes

Kato

Ohtani

et al. 2022

Chem. Soc. Rev.

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“…During the past decades, MIMs have drawn a tremendous interest not only due to their smart architectures but also due to their potential applications in various fields ( Sluysmans et al, 2019 ; Cornelissen et al, 2021 ; David et al, 2021 ). [1]Rotaxanes, which are composed of “T”-shaped axles and macrocyclic wheels and the axles are threaded by their own wheels and connected by covalent bonds, are considered as the fundamental supramolecular systems for the construction of diverse MIMs ( Tian et al, 2018 ; Scheme 1 ). It is known that there is a huge challenge for the efficient synthesis of [1]rotaxanes due to their subtle structures.…”

Section: Introductionmentioning

confidence: 99%

Construction and Property Investigation of Serial Pillar[5]arene-Based [1]Rotaxanes

Han

Yan

et al. 2022

Front. Chem.

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Although the construction and application of pillar[5]arene-based [1]rotaxanes have been extensively studied, the types of stoppers for them are limited. In this work, we designed and prepared three series of pillar[5]arene-based [1]rotaxanes (P5[1]Rs) with pentanedione derivatives, azobenzene derivatives, and salicylaldehyde derivatives as the stoppers, respectively. The obtained P5[1]Rs were fully characterized by NMR (1H, 13C, and 2D), mass spectra, and single-crystal X-ray analysis. We found that the synergic C–H···π, C–H···O interactions and N–H···O, O–H···N hydrogen bonding are the key to the stability of [1]rotaxanes. This work not only enriched the diversity of pillar[n]arene family but also gave a big boost to the pillar[n]arene-based mechanically interlocked molecules

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Synthesis and characterization of a new pillar[5]arene-based [1]rotaxane

Cited by 13 publications

References 45 publications

Cross-Linked Supramolecular Polymer Based on Calix[4]pyrrole-Decorated Pillar[5]arene and Its Application in Micropollutant Removal

Cross-Linked Supramolecular Polymer Based on Calix[4]pyrrole-Decorated Pillar[5]arene and Its Application in Micropollutant Removal

Noncovalently bound and mechanically interlocked systems using pillar[n]arenes

Construction and Property Investigation of Serial Pillar[5]arene-Based [1]Rotaxanes

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