A Novel Phosphate Chemosensor Utilizing Anion-Induced Fluorescence Change

Liao, Jen-Hai; Chen, Chao‐Tsen; Fang, Jim‐Min

doi:10.1021/ol0171564

Cited by 130 publications

(50 citation statements)

References 37 publications

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“…[23] The anion that was bound to with the amino group of 2·Cu I should reduce its participation in PET quenching of the naphthalene, and thus enhance the fluorescence emission. Moreover, no excimer emission was observed owing to the insertion of anions that caused the two naphthalenes to move away from each other.…”

Section: Full Papermentioning

confidence: 99%

Cooperative Recognition of a Copper Cation and Anion by a Calix[4]arene Substituted at the Lower Rim by a β‐Amino‐α,β‐Unsaturated Ketone

Senthilvelan

Chang

et al. 2009

Chemistry A European J

109

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We report herein a new ditopic calix[4]arene receptor 25,27-bis-{[4-amino-4-(1-naphthyl)-2-oxo-3-butenyl]oxy}-26,28-dihydroxycalix[4]arene (2) for the simultaneous complexation of anionic and cationic species. The host molecule 25,27-bis{[3-(1-naphthyl)-5-isoxazolyl]methoxy}-26,28-dihydroxycalix[4]arene (1) was synthesised first and was followed by a [Mo(CO)6]-mediated ring-opening reaction to give the target receptor 2. The binding properties of ligands 1 and 2 towards metal ions in CH3CN were investigated by UV/Vis and fluorescence spectroscopies. The results showed that both ligands 1 and 2 were highly selective for Cu(II) ions. Upon titration with Cu(II), the fluorescence of 1 was severely quenched, whereas 2 showed strong fluorescence enhancement because the metal ions help to lock the conformation of the fluorophores. During the complexation of 2 with Cu(II), the Cu(II) was reduced to Cu(I) by the free phenolic OH of 2, whereas the phenol was oxidised by Cu(II), after which it assisted in the trapping of Cu(I). Ditopic behaviour was observed for the complex 2.Cu(I), which showed further enhancement of its fluorescence intensity upon complexation with anions such as acetate or fluoride.

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Section: Full Papermentioning

confidence: 99%

Cooperative Recognition of a Copper Cation and Anion by a Calix[4]arene Substituted at the Lower Rim by a β‐Amino‐α,β‐Unsaturated Ketone

Senthilvelan

Chang

et al. 2009

Chemistry A European J

109

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“…Its function is based on the fact that in one of the sensor states, when with bound or unbound target molecules, the two fluorophore molecules are close to each other but distant enough to form an excimer upon excitation, while in the other state they move apart and excimers are not observed. This was the idea of Yang et al in the construction of sensors for cations (Yang, Lin et al, 2001;Liao, Chen et al, 2002) when constructing a sensor for anions. Furthermore, since pyrene is a fluorophore that can easily form excimers, it has been used for the construction of sensors for DNA detection, as described by Mahara et al (Mahara, Iwase et al, 2002) as it needs the formation of pyreneconjugated oligonucleotides where excimers can occur or in sensor for protein-protein recognition, as described by Sahoo et al (Sahoo, Narayanaswami et al, 2000) Martins et al (Martins et al, 2011 in press) showed that peptide nanostructures containing pyrene derivatives sorbed onto them can sense distinct environments, with effect on fluorescence lifetimes, even when excimer are not formed.…”

Section: Fluorescence-based Biosensorsmentioning

confidence: 99%

Biosensors Based on Biological Nanostructures

Alves¹,

Alves²,

Sousa³

et al. 2011

New Perspectives in Biosensors Technology and Applications

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“…]DMSO), [26] and amido-pyrrole-based receptors (K H 2 PO 4 À/K OAc À = 5-30 also in [D 6 ]DMSO). [27][28][29] …”

Section: Introductionmentioning

confidence: 99%

Expanding Sapphyrin: Towards Selective Phosphate Binding

Katayev

Boev

Myshkovskaya

et al. 2008

Chemistry A European J

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The anion-templated syntheses and binding properties of novel macrocyclic oligopyrrole receptors in which pyrrole rings are linked through amide or imine bonds are described. The efficient synthesis was accomplished by anion-templated [1+1] Schiff-base condensation and acylation macrocyclization reactions. Free receptors and their host-guest complexes with hydrochloric acid, acetic acid, tetrabutylammonium chloride, and hydrogen sulfate were analyzed by single-crystal X-ray diffraction analysis. Stability constants with different tetrabutylammonium salts of inorganic acids were determined by standard 1H NMR and UV/Vis titration techniques in [D6]DMSO/0.5% water solution. According to the titration data, receptors containing three pyrrole rings (10 and 12) exhibit high affinity (log Ka=5-7) for bifluoride, acetate, and dihydrogen phosphate, and interact weakly with chloride and hydrogen sulfate. The amido-bipyrrole receptors 11 and 13 with four pyrrole rings exhibit 10(4)- and 10(2)-fold selectivity for dihydrogen phosphate, respectively, as inferred from competitive titrations in the presence of tetrabutylammonium acetate.

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A Novel Phosphate Chemosensor Utilizing Anion-Induced Fluorescence Change

Cited by 130 publications

References 37 publications

Cooperative Recognition of a Copper Cation and Anion by a Calix[4]arene Substituted at the Lower Rim by a β‐Amino‐α,β‐Unsaturated Ketone

Cooperative Recognition of a Copper Cation and Anion by a Calix[4]arene Substituted at the Lower Rim by a β‐Amino‐α,β‐Unsaturated Ketone

Biosensors Based on Biological Nanostructures

Expanding Sapphyrin: Towards Selective Phosphate Binding

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