Chiral pillar[n]arenes: Conformation inversion, material preparation and applications

Shi, Chengxiang; Li, Hui; Shi, Xiaofeng; Zhao, Liang; Qiu, Hongdeng

doi:10.1016/j.cclet.2021.12.010

Cited by 45 publications

(15 citation statements)

References 102 publications

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“…, butylbenzene (4), amylbenzene (5), hexylbenzene (6), benzene (7), naphthalene (8), anthracene (9), and tetracene (10). Mobile phase: 60% ACN in water for three Sil-TPE and 80% ACN in water for C18.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…High performance liquid chromatography (HPLC) is a very important separation and analysis technology developed in the late 1960s . With the emergence of new methods and new technologies, HPLC has made great progress in separation and analysis. − As the core of HPLC, stationary phases play a key role in separation and analysis. Surface modification is the main route to get different bonding phases, which were divided into normal phase, reverse phase, hydrophilic phase, and so forth. − Actually, most of the separation can be completed by reversed-phase liquid chromatography (RPLC).…”

Section: Introductionmentioning

confidence: 99%

“…Relationships between log k and log P for three Sil-TPE (A−C) and C18 columns (D). Analytes: toluene (1), ethylbenzene (2), propylbenzene (3), butylbenzene (4), amylbenzene (5), hexylbenzene(6), benzene(7), naphthalene(8), anthracene(9), and tetracene(10). Mobile phase: 60% ACN in water for three Sil-TPE and 80% ACN in water for C18.…”

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confidence: 99%

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Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

et al. 2022

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Surface modification is an effective way to functionalize the materials so as to get some special properties. Tetraphenylethylene (TPE) has been widely investigated as a well-known reagent which has the nature of aggregation-induced emission (AIE), but has never been reported in the liquid chromatography stationary phase. In this work, TPE-grafted silica (Sil-TPE) was obtained successfully using the derivative of 1-(4-hydroxyphenyl)-1,2,2-triphenylethylene as a ligand, and then characterized by elemental analysis, Fourier transform infrared spectra, thermogravimetric analysis, and so forth. Laser scanning confocal microscopy images reflected the AIE phenomenon of grafted TPE because the internal vibration and rotation of TPE molecules were restrained in the confined silica space. The contact angle test showed superhydrophobic properties of Sil-TPE. In order to understand thoroughly the mechanism of chromatographic performance and retention behavior for Sil-TPE, Tanaka test mixture, alkylbenzenes, polycyclic aromatic hydrocarbons (PAHs), and phenols were separated. This reveals that Sil-TPE has strong aromaticity and certain shape selectivity, especially, has excellent separation performance for PAHs and phenols. The thermodynamic properties and repeatability of Sil-TPE were further studied, which showed the stability of Sil-TPE. This work shows that TPE can be successfully grafted on silica surface and it has the potential to be a new kind of promising stationary phases in the future.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

et al. 2022

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“…Among nonalkoxy derivatives, aryl-substituted ones are of particular importance because direct attachment of π-conjugated moieties enables various π-electron-derived functions as well as π-extension of core benzene units. Although functional segments could be introduced also via alkoxy linkers, interrupted electronic and structural communications were not suitable for the efficient combination of planar chirality and host–guest ability of pillar[ n ]arene cores . Therefore, direct incorporation of aryl substituents exhibits unique advantages for the development of pillar[ n ]arene-based multifunctional and switching systems.…”

Section: Introductionmentioning

confidence: 99%

Per-Arylation of Pillar[n]arenes: An Effective Tool to Modify the Properties of Macrocycles

et al. 2023

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Installation of various substituents is a reliable and versatile way to alter the properties of macrocyclic molecules, but high-yield and controlled methods are not always available especially for multifold reactions. Herein, we report 10- and 12-fold introduction of aryl substituents onto both rims of cylinder-shaped pillar[n]arenes, which usually have alkoxy substituents slanting to the cylinder axes. Although alkoxy pillar[5]arenes exist as D 5-symmetric enantiomeric pairs, arylated pillar[5]arenes provide crushed single-crystal structures and stereoisomerism including C 2-symmetric conformations depending on the aryl groups. Pillar[n]arenes with 2-benzofuranyl groups display bright fluorescence with quantum yields of 88–90% and no host–guest complexation with electron-deficient molecules in solution due to large deviation from alkoxy compounds. A benzofuran-appended pillar[6]arene instead captures small gaseous molecules in the solid state, probably owing to outside spaces surrounded by aromatic rings.

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“…[3][4][5] Chiral stationary phases prepared by compounding chiral polymers, cyclodextrins, cellulose, crown ethers, pillararenes and their derivatives on silica surfaces by coating and bonding them have been widely reported for achieving enantioseparation when performing chiral chromatography. [6][7][8][9][10][11][12][13][14] However, the relatively few available chiral stationary phases make it difficult to meet the current needs involving an increasing variety of chiral substances with a wide range of structures. Therefore, it is important to develop new chiral stationary phases to expand the range of chiral separations.…”

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Synthesis of chiral functionalized UiO-66-NH₂@SiO₂and use of its domain-limiting effect for separating small enantiomers

Liu

Quan

et al. 2022

Chem. Commun.

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Chiral pillar[n]arenes: Conformation inversion, material preparation and applications

Cited by 45 publications

References 102 publications

Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

Per-Arylation of Pillar[n]arenes: An Effective Tool to Modify the Properties of Macrocycles

Synthesis of chiral functionalized UiO-66-NH₂@SiO₂and use of its domain-limiting effect for separating small enantiomers

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Chiral pillar[n]arenes: Conformation inversion, material preparation and applications

Cited by 45 publications

References 102 publications

Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

Grafting of Tetraphenylethylene on Silica Surface, Characterizations, and Their Chromatographic Performance as Reversed-Phase Stationary Phases

Per-Arylation of Pillar[n]arenes: An Effective Tool to Modify the Properties of Macrocycles

Synthesis of chiral functionalized UiO-66-NH2@SiO2and use of its domain-limiting effect for separating small enantiomers

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Synthesis of chiral functionalized UiO-66-NH₂@SiO₂and use of its domain-limiting effect for separating small enantiomers