Tetrahedral Anions Selective Fluorescent Calix[6]arene Receptor Containing Urea and Pyrene Moieties

Jeon, Nam Joong; Ryu, Byung Ju; Park, Ki Deok; Lee, Young Ju; Nam, Kye Chun

doi:10.5012/bkcs.2010.31.12.3809

Cited by 9 publications

(4 citation statements)

References 14 publications

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“…Different fluorophores like naphthalene, anthracene and pyrene are among the most incorporated in the calixarene framework, leading to fluorescent probes for the recognition of different types of analytes. Examples of fluorescent calix[4]arene [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ], calix[5]arene [ 14 ] and calix[6]arene [ 15 , 16 ] receptors have been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Miranda

Marcos

Ascenso³

et al. 2022

Molecules

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Fluorescent receptors (4a–4c) based on (thio)ureido-functionalized hexahomotrioxacalix[3]arenes were synthesised and obtained in the partial cone conformation in solution. Naphthyl or pyrenyl fluorogenic units were introduced at the lower rim of the calixarene skeleton via a butyl spacer. The binding of biologically and environmentally relevant anions was studied with NMR, UV–vis absorption, and fluorescence titrations. Fluorescence of the pyrenyl receptor 4c displays both monomer and excimer fluorescence. The thermodynamics of complexation was determined in acetonitrile and was entropy-driven. Computational studies were also performed to bring further insight into the binding process. The data showed that association constants increase with the anion basicity, and AcO−, BzO− and F− were the best bound anions for all receptors. Pyrenylurea 4c is a slightly better receptor than naphthylurea 4a, and both are more efficient than naphthyl thiourea 4b. In addition, ureas 4a and 4c were also tested as ditopic receptors in the recognition of alkylammonium salts.

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Section: Introductionmentioning

confidence: 99%

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Miranda

Marcos

Ascenso³

et al. 2022

Molecules

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“…Fluorogenic moieties, such as naphthalene, anthracene and pyrene are among the most incorporated in the calixarene framework, leading to the development of fluorescent probes for anion and also ion-pair recognition. Examples of such fluorescent calix[4] arene [ 5 , 6 , 7 , 8 , 9 , 10 ], calix[5] arene [ 11 ] and calix[6]arene [ 12 , 13 , 14 ] receptors have been reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Dihomooxacalix[4]arene-Based Fluorescent Receptors for Anion and Organic Ion Pair Recognition

et al. 2020

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Fluorescent dihomooxacalix[4]arene-based receptors 5a–5c, bearing two naphthyl(thio)ureido groups at the lower rim via a butyl spacer, were synthesised and obtained in the cone conformation in solution. The X-ray crystal structures of 1,3- (5a) and 3,4-dinaphthylurea (5b) derivatives are reported. Their binding properties towards several anions of different geometries were assessed by 1H-NMR, UV-Vis absorption and fluorescence titrations. Structural and energetic insights of the naphthylurea 5a and 5b complexes were also obtained using quantum mechanical calculations. The data showed that all receptors follow the same trend, the association constants increase with the anion basicity, and the strongest complexes were obtained with F−, followed by the oxoanions AcO− and BzO−. Proximal urea 5b is a better anion receptor compared to distal urea 5a, and both are more efficient than thiourea 5c. Compounds 5a and 5b were also investigated as heteroditopic receptors for biologically relevant alkylammonium salts, such as the neurotransmitter γ-aminobutyric acid (GABA·HCl) and the betaine deoxycarnitine·HCl. Chiral recognition towards the guest sec-butylamine·HCl was also tested, and a 5:2 selectivity for (R)-sec-BuNH3+·Cl− towards (P) or (M) enantiomers of the inherently chiral receptor 5a was shown. Based on DFT calculations, the complex [(S)-sec-BuNH3+·Cl−/(M)-5a] was indicated as the more stable.

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“…To date, many of the reported HSO 4 − anion receptors have relied on hydrogen-bonding motifs [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23], which enables them to interact with HSO 4 − as well as a few other tetrahedral analytes such as HClO 4 , ClO 4 − , H 2 PO 4 − A c c e p t e d M a n u s c r i p t 6 temperature was raised to 50 0 C, and the mixture was stirred for an additional 2 h. The reaction mixture was cooled to room temperature and slowly poured into saturated aqueous NaHCO 3 under ice-cold conditions till no gas formed. After being warmed to room temperature, the reaction mixture was further stirred for 30 min and washed with water.…”

Section: Introductionmentioning

confidence: 99%

A fluorescent turn-on probe for detection of HSO4− ion based on hydrolysis of BODIPY-derived Schiff base with chromogenic and fluorogenic dual signals

Wang

Fang

et al. 2016

Sensors and Actuators B: Chemical

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Tetrahedral Anions Selective Fluorescent Calix[6]arene Receptor Containing Urea and Pyrene Moieties

Cited by 9 publications

References 14 publications

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Anion Binding by Fluorescent Ureido-Hexahomotrioxacalix[3]arene Receptors: An NMR, Absorption and Emission Spectroscopic Study

Dihomooxacalix[4]arene-Based Fluorescent Receptors for Anion and Organic Ion Pair Recognition

A fluorescent turn-on probe for detection of HSO4− ion based on hydrolysis of BODIPY-derived Schiff base with chromogenic and fluorogenic dual signals

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