Desymmetrized Leaning Pillar[6]arene

Wu, Jia‐Rui; Mu, Anthony U.; Li, Bao; Wang, Chunyu; Fang, Lei; Yang, Ying‐Wei

doi:10.1002/ange.201805980

Cited by 44 publications

(6 citation statements)

References 75 publications

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“…More importantly, methanesulfonic acid could promote the reaction by binding with in situ generated by‐product H 2 O. As a result, BrEtTrimer was obtained in a yield of 52 %, and IEtTrimer was obtained in a yield of 82 %, which is significantly higher than 35 %, the yield of the trimer for synthesizing the perethylated leaning pillar[6]arene [33] . The fact that the yield of BrEtTrimer was lower than IEtTrimer can be explained by the stronger electron‐withdrawing effect of bromine atom over iodine atom.…”

Section: Resultsmentioning

confidence: 99%

“…Although one‐pot synthesis of macrocycles [24–29] is quite fascinating, two‐step fragment coupling has also attracted much attention, as this approach could incorporate different repeating units onto the macrocycles in the first place [30–46] . It occurred to us that this strategy could be feasible for synthesizing symmetrically tetra‐functionalized pillar[6]arenes.…”

Section: Introductionmentioning

confidence: 99%

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Symmetrically Tetra‐functionalized Pillar[6]arenes Prepared by Fragment Coupling

et al. 2022

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Due to the highly symmetrical structures generated from one‐pot syntheses, the partial functionalization of macrocycles is usually beset with low yields and onerous purifications of the target multifunctional macrocycles. To improve this situation, taking pillar[6]arenes as an example, a two‐step fragment coupling method has been developed for synthesizing symmetrically tetra‐functionalized pillar[6]arenes, namely X‐pillar[6]arenes. This method is simple and versatile, which makes hetero‐fragment coupling and pre‐functionalization available. Nine new macrocycles and a pillar[6]arene‐based cage have been prepared. In addition, one of the newly synthesized macrocycles, COOEtEtXP[6], exhibits a strong cyan luminescence in the solid state under irradiation by 365 nm UV light. This emission originates from intramolecular through‐space conjugation. Meanwhile, formation of a supramolecular polymer by multiple non‐covalent intra/intermolecular interactions helps rigidify the structure and make COOEtEtXP[6] an efficient solid‐state emitter. It is believed that this fragment coupling can also be used to realize the multi‐functionalization of other macrocycles.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Symmetrically Tetra‐functionalized Pillar[6]arenes Prepared by Fragment Coupling

et al. 2022

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“…2). The upfield shifting of the protons belonging to BCB, sourcing from inclusion-induced shielding effect, and the 2D NOESY analysis between H(a−d) of host and H(2-5) of guest groups further illustrate the insertion of BCB into the cavity of TBP 38 . The titration experiment under a fixed BCB concentration (4.0 mM) suggests a slow exchange referring to NMR timescale (Supplementary Fig.…”

Section: Host-guest Interaction Between (Tbp) 4 Siw and Ditopic Guestmentioning

confidence: 93%

Processing supramolecular framework for free interconvertible liquid separation

Zhang

Zhou

et al. 2020

Nat Commun

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Nanoporous structures constructed by small molecular components exhibited vigorous materials potentials. While maintianing uniform porosity and functional properties, more applicable processing methods for the solid powders need to be considered and the improvement of binding interactions represents a preferable approach for structural flexibility. Here, by combining ionic interaction and host-guest inclusion, we constructed flexible supramolecular frameworks composing of inorganic polyanionic clusters, cationic organic hosts, and a bridging guest. The formed layer framework structure assemblies grew into nano-fibers and then supramolecular gels, donating highly convenient processability to porous materials. A simple spin-coating generated a new type of liquid separation membranes which showed structural stability for many liquids. The surface properties can be facilely modulated via filling a joystick liquid and then a hydrophilic/hydrophobic liquid into the porous frameworks, providing in-situ consecutive switchings for cutting liquids. This strategy extends the potential of flexible supramolecular frameworks for responsive materials in the laboratory and in industry.

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“…Acridine orange (ΑΟ) and trinitrophenol (TNP) were acquired from Sigma Chemical Co. (St. Louis, MO, USA). PCP6 was synthesized according to the literature, [52][53][54] and the synthetic route is shown in Scheme S1. The structure and purity of all compounds were confirmed by 1 H NMR and 13 C NMR (see Figs.…”

Section: Reagentsmentioning

confidence: 99%

A Facile and High Selectivity Novel Fluorescence Sensing Determination of 2, 4, 6-Trinitrophenol Based on Cationic Water-Soluble Pillar[6]arene Graphene Nanocomposite

Tan¹,

Zhang²,

Zeng³

et al. 2018

Preprint

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We describe a selective and sensitive fluorescence platform for the detection of trinitrophenol (TNP) based on competitive host–guest recognition between pyridine-functionalized pillar[6]arene (PCP6) and probe (acridine orange, AO) that used PCP6-functionalized reduced graphene (PCP6-rGO) as the receptor. TNP is an electron-deficient and negative molecule which is captured by PCP6 via electrostatic interactions and π-π interactions. Therefore, a selective and sensitive fluorescence sensor for TNP detection is developed. It has a low detection limit of 0.0035 μM (S/N=3) and a wider linear response of 0.01−5.0 and 5.0−125.0 for TNP. The sensing platform is also used to test TNP in two water and soil samples with satisfying results. This suggests that this approach has potential applications for the determination of TNP.

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Desymmetrized Leaning Pillar[6]arene

Cited by 44 publications

References 75 publications

Symmetrically Tetra‐functionalized Pillar[6]arenes Prepared by Fragment Coupling

Symmetrically Tetra‐functionalized Pillar[6]arenes Prepared by Fragment Coupling

Processing supramolecular framework for free interconvertible liquid separation

A Facile and High Selectivity Novel Fluorescence Sensing Determination of 2, 4, 6-Trinitrophenol Based on Cationic Water-Soluble Pillar[6]arene Graphene Nanocomposite

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