Monolayer of a Na<sup>+</sup>-Selective Fluoroionophore on Glass:  Connecting the Fields of Monolayers and Optical Detection of Metal Ions

Veen, Niels J. van der; Flink, Simon; Deij, M.A.; Egberink, Richard J.M.; Veggel, Frank C. J. M. van; Reinhoudt, David N.

doi:10.1021/ja000713h

Cited by 120 publications

(81 citation statements)

References 22 publications

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“…216 This was the first example of the detection of metal ions by fluorescence using a monolayer of a selective receptor. The novelty of this work was that it offered an alternative to physical immobilization of fluoroionophores in membranes.…”

Section: Glass and Gold Surfacesmentioning

confidence: 99%

Design of fluorescent materials for chemical sensing

2007

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There is an enormous demand for chemical sensors for many areas and disciplines. High sensitivity and ease of operation are two main issues for sensor development. Fluorescence techniques can easily fulfill these requirements and therefore fluorescent-based sensors appear as one of the most promising candidates for chemical sensing. However, the development of sensors is not trivial; material science, molecular recognition and device implementation are some of the aspects that play a role in the design of sensors. The development of fluorescent sensing materials is increasingly captivating the attention of the scientists because its implementation as a truly sensory system is straightforward. This critical review shows the use of polymers, sol-gels, mesoporous materials, surfactant aggregates, quantum dots, and glass or gold surfaces, combined with different chemical approaches for the development of fluorescent sensing materials. Representative examples have been selected and they are commented here.

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Section: Glass and Gold Surfacesmentioning

confidence: 99%

Design of fluorescent materials for chemical sensing

2007

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“…Relatively recently, Reinhoudt et al (19)(20)(21)(22) and Bryce et al (23,24) reported, almost simultaneously, the incorporation of crownether groups into SAMs and their use as potential metal ion sensors. The Reinhoudt group used electrochemical impedance spectroscopy (EIS) for SAM characterization and to study the ion recognition processes (19)(20)(21)(22).…”

mentioning

confidence: 99%

“…The Reinhoudt group used electrochemical impedance spectroscopy (EIS) for SAM characterization and to study the ion recognition processes (19)(20)(21)(22). This technique enables the detection of interfacial ion recognition phenomena when both guest ion and host monolayer are electrochemically inactive, by detecting changes of the charge-transfer resistance induced by metal ion binding (see Fig.…”

mentioning

confidence: 99%

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Herranz

Colonna

Echegoyen

2002

Proc. Natl. Acad. Sci. U.S.A.

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Our recent work with cyclic and acyclic polyether self-assembled monolayers (SAMs) on gold is presented. A series of dithia-crowntetrathiafulvalene derivatives with one or two disulfide groups has been prepared, and their SAMs on gold have been characterized by electrochemistry and by reflection-absorption infrared spectroscopy. These SAMs are extremely stable on repeated electrochemical potential scans and can selectively recognize alkali metal ions. Acyclic polyether derivatives can also self-assemble on gold to yield selective metal ion recognition domains. Impedance spectroscopy data for these SAMs fit the Langmuir isotherm and allow the determination of ion association constants. Some of the SAMs prepared with new acyclic polyether derivatives are able to detect potassium cations selectively when templated in their presence. These structures are believed to be a consequence of ion ''imprinting'' during the process of SAM formation.T he easy preparation, stability, and versatility of self-assembled monolayers (SAMs) has resulted in considerable activity in this field since the first publication by Nuzzo and Allara (1). Molecular recognition is especially relevant on surfaces because it allows the control of the exchange of signals, structures, and energy through the interfaces (2-4). SAMs allow the introduction of functional groups in the adsorbates, thus offering a powerful way to develop systems that have applications as sensors, devices, and switches (5). Some recent articles have reported surface structures with hydrophobic and hydrophilic properties arranged in nano-strips and honeycomb or homogeneous structures (6), whereas others have detected photo and electrochemical conversion of cis to trans forms within the SAM (7). Other examples have shown the formation of chiral imprinted sites (8). SAM structures have also been prepared for the recognition and sensing of metal ions (9), some of which are electrochemically active (10-18).Relatively recently, and Bryce et al. (23,24) reported, almost simultaneously, the incorporation of crownether groups into SAMs and their use as potential metal ion sensors. The Reinhoudt group used electrochemical impedance spectroscopy (EIS) for SAM characterization and to study the ion recognition processes (19)(20)(21)(22). This technique enables the detection of interfacial ion recognition phenomena when both guest ion and host monolayer are electrochemically inactive, by detecting changes of the charge-transfer resistance induced by metal ion binding (see Fig. 1a; refs. 25 and 26). The report by Bryce et al. (23,24) described SAMs of crown-annelated tetrathiafulvalene (TTF) derivatives, which showed, by cyclic voltammetry (CV), a redox potential shift of the electroactive, surface-confined, crown-TTF group on ion complexation (23, 24). The first TTF-crown SAMs reported by this group were apparently unstable after several electrochemical scans (23). However, in a subsequent report they demonstrated that the stability and electrochemical behavior of the SAMs can be improv...

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“…Compound 1 was prepared by the reaction of diaza-18-crown-6 ether with 2-chloro-N-pyren-1-yl-acetamide 10 in the presence of triethylamine in EtOH. 11 The compound was designed by combining the two well-known molecular motifs of diaza-crown binding site and frequently employed signaling handle of pyrenylacetamide subunit.…”

Section: Resultsmentioning

confidence: 99%

Pyrene Appended Hg²⁺-selective Fluoroionophore Based upon Diaza-Crown Ether

Choi¹,

Kim²,

Chang

2008

Bulletin of the Korean Chemical Society

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A new pyrene appended diaza-18-crown-6 ether derivative 1 has been prepared and its fluoroionophoric properties toward transition metal ions were investigated. Compound 1 exhibited a high Hg 2+ -selectivity over other transition metal ions as well as alkali and alkaline earth metal ions in aqueous acetonitrile solution. The ratiometric analysis of the monomer and excimer emissions of pyrene successfully signals the presence of Hg 2+ ions. The detection limit for Hg 2+ ions was found to be 3.1 × 10 −6 M in 50% aqueous acetonitrile solution at pH 8.1. Competition experiments also suggest that the compound could be utilized as a selective and sensitive fluorescent chemosensor for the analysis of micromolar Hg 2+ ions in physiological and environmental samples.

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Monolayer of a Na⁺-Selective Fluoroionophore on Glass: Connecting the Fields of Monolayers and Optical Detection of Metal Ions

Cited by 120 publications

References 22 publications

Design of fluorescent materials for chemical sensing

Design of fluorescent materials for chemical sensing

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Pyrene Appended Hg²⁺-selective Fluoroionophore Based upon Diaza-Crown Ether

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Monolayer of a Na+-Selective Fluoroionophore on Glass: Connecting the Fields of Monolayers and Optical Detection of Metal Ions

Cited by 120 publications

References 22 publications

Design of fluorescent materials for chemical sensing

Design of fluorescent materials for chemical sensing

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Pyrene Appended Hg2+-selective Fluoroionophore Based upon Diaza-Crown Ether

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Product

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Monolayer of a Na⁺-Selective Fluoroionophore on Glass: Connecting the Fields of Monolayers and Optical Detection of Metal Ions

Pyrene Appended Hg²⁺-selective Fluoroionophore Based upon Diaza-Crown Ether