Synthesis of a facile fluorescent 8-hydroxyquinoline-pillar[5]arene chemosensor based host-guest chemistry for phoxim

Cheng, Ming; Li, Guang; Xu, Weiwei; Qu, Haonan; Mao, Xiaowei; Li, Haibing

doi:10.1016/j.dyepig.2021.109646

Cited by 11 publications

(3 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…9,10 A simple suction filtration of the solid complex effectively separates this preferred isomer from the remaining components in the mixture; mild heat or chromatography is then normally adequate in order to isolate the guest from the complex, and the host compound may thereafter be readily recycled in the process. The field of host−guest chemistry has found numerous applications in drug and gene delivery 11,12 and in chemosensing, 13 among numerous others. Another important use of this field of science is in the separation of isomers.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction

Barnardo,

Barton,

Caira

et al. 2024

Crystal Growth & Design

View full text Add to dashboard Cite

In this investigation, potential host compounds N, N′-bis(9-phenyl-9-xanthenyl)propane-1,3-diamine (H1) and N, N′-bis(9-phenyl-9-xanthenyl)butane-1,4-diamine (H2) were crystallized from pure single solvents and mixtures of guests comprising xylenes (oXy, mXy, and pXy) and ethylbenzene (EB). Although H1 successfully enclathrated oXy in the single solvent experiment, this host compound was not able to extract oXy when presented with various mixtures of these guest compounds, and only the guest-free host compound was ultimately recovered from these crystallization experiments. H2, on the other hand, successfully included both oXy and pXy. Thermal experiments on H2•pXy and H2•1.5(oXy) showed that the former complex was more stable than the latter. Single-crystal X-ray diffraction (SCXRD) experiments were employed to analyze the conformations of both host molecules when guest-free and in the presence of the guest species. Experiments involving equimolar binary guest mixtures and H2 revealed that this host compound was selective for oXy whenever it was present. Furthermore, from experiments employing H2 and pXy/mXy (40:60, 50:50, and 60:40 mol %) binary mixtures, remarkable K values (the selectivity coefficient) were calculated in favor of pXy, suggesting that host−guest chemistry strategies may be used to effectively separate these difficult-to-separate mixtures when H2 is the host compound.

show abstract

Section: Introductionmentioning

confidence: 99%

“…The field of host–guest chemistry has found numerous applications in drug and gene delivery , and in chemosensing, among numerous others. Another important use of this field of science is in the separation of isomers .…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction

Barnardo,

Barton,

Caira

et al. 2024

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…10 The intermolecular interaction and spatial structure of these host–guest systems change dynamically and reversibly according to specific stimulus. Various stimuli-responsive host–guest systems have been applied in different fields, such as fluorescent sensors, 11 drug delivery systems, 12 and smart functional materials. 13,14…”

Section: Introductionmentioning

confidence: 99%

Controlled release of drug molecules by pillararene-modified nanosystems

Yang

Zhang

et al. 2022

Chem. Commun.

Self Cite

View full text Add to dashboard Cite

show abstract

Construction of a Supramolecular Fluorescence Sensor from Water‐soluble Pillar[5]arene and 1‐Naphthol for Recognition of Metal Ions

et al. 2021

View full text Add to dashboard Cite

A new fluorescent chemosensor comprised of a pyridine functionalized pillar[5]arene (PyP5) and 1‐naphthol has been designed and utilized for the recognition of metal cations. The 1‐naphthol was encapsulated by the PyP5 cavity and formed a 1 : 1 host ‐ guest inclusion complex. Whilst free 1‐naphthol is known to be strongly fluorescent, this strong fluorescence was quenched in the inclusion complex 1‐naphthol@PyP5. Using the 1‐naphthol@PyP5 inclusion complex as a fluorescent probe, various metal cations have been detected. The experimental results revealed that the probe responded to both Ag+ and Fe3+, via an obvious fluorescence quenching or an incomplete quenching of fluorescence, respectively. As a result, a fluorescence method for the detection of two metal cations using a single system has been developed. On the other hand, 1‐naphthol is an important intermediate of fine chemicals, which is widely used in the synthesis and production of dyes, spices, oils, medicines and pesticides.[50–52] The oxygen atom of 1‐naphthol is sp2 hybridized and can form extensive π bonds, and can exhibit strong fluorescence. The successful preparation of water‐soluble pillar[5]arene can provide new opportunities for chemists working in the field of host–guest chemistry and the recognition of metal ions. Therefore, more and more research has centered on the synthesis of water‐soluble pillar[5]arenes.[53–56] On this basis, we have synthesized a pyridine functionalized pillar[5]arene. Pyridine functionalized pillar[5]arenes are extremely soluble in water and strongly bind 1‐naphthol in water, which is mainly driven by hydrophobic and electrostatic interactions. The probe system is constructed by encapsulating one equivalent of 1‐naphthol, which possess strong intrinsic fluorescence, into the hydrophobic cavity of PyP5. To this inclusion complex, namely 1‐naphthol@PyP5, were added metal ions. The addition of Ag+ led to incomplete quenching of fluorescence, whilst Fe3+ led to complete quenching of fluorescence. Based on the linear relationship between the fluorescence intensity and the concentration of Ag+ and Fe3+, a simple fluorescent probe method for the analysis of Ag+ and Fe3+ was constructed. The observed visual signals indicate the potential of this probe system in rapid assay applications.

show abstract

Synthesis of a facile fluorescent 8-hydroxyquinoline-pillar[5]arene chemosensor based host-guest chemistry for phoxim

Cited by 11 publications

References 38 publications

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction

Controlled release of drug molecules by pillararene-modified nanosystems

Construction of a Supramolecular Fluorescence Sensor from Water‐soluble Pillar[5]arene and 1‐Naphthol for Recognition of Metal Ions

Contact Info

Product

Resources

About

Synthesis of a facile fluorescent 8-hydroxyquinoline-pillar[5]arene chemosensor based host-guest chemistry for phoxim

Cited by 11 publications

References 38 publications

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C8H10 Aromatic Crude Oil Fraction

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C8H10 Aromatic Crude Oil Fraction

Controlled release of drug molecules by pillararene-modified nanosystems

Construction of a Supramolecular Fluorescence Sensor from Water‐soluble Pillar[5]arene and 1‐Naphthol for Recognition of Metal Ions

Contact Info

Product

Resources

About

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction

Evaluation of the Behavior of Two Tricyclic-Fused Host Systems in the Presence of Single and Mixed Isomers of the C₈H₁₀ Aromatic Crude Oil Fraction