Recognition of Cations by Self-Assembled Monolayers of Crown Ethers

Flink, Simon; Veggel, van Frank C.J.M.; Reinhoudt, David N.

doi:10.1021/jp990014v

Cited by 99 publications

(100 citation statements)

References 17 publications

(34 reference statements)

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“…6 The molecular recognition process can be detected sensibly by IR spectroscopy, 3 quartz crystal microbalance (QCM), 4,5 surface plasmon resonance (SPR), 6 and electrochemical measurements. [7][8][9][10] The SAMs of ␣-helical peptides that oriented nearly vertically to the surface were successfully reported. 11 The molecular diameter of the helix is about 1 nm, which is more than 3-fold of that of general alkanethiols.…”

Section: Introductionmentioning

confidence: 99%

Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit

et al. 2000

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Section: Introductionmentioning

confidence: 99%

Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit

et al. 2000

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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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“…[ 7 ] Moreover, OEG monolayers provide a very suited environment to coordinate cations by oxygen atoms. These binding motifs tend to form cage structures within the SAM, comparable to crown ethers [ 8,9 ] or cryptates. [ 10 ] Recently it was shown that OEG-based molecules with thiol anchors-which form striped patterns on gold nanoparticles in combination with short n -alkyl thiols-can effi ciently and selectively trap cations and thus serve as a sensitive sensor.…”

Section: Doi: 101002/adma201503911mentioning

confidence: 99%

Improving the Performance of Organic Thin‐Film Transistors by Ion Doping of Ethylene‐Glycol‐Based Self‐Assembled Monolayer Hybrid Dielectrics

Dietrich

Scheiner²,

Portilla³

et al. 2015

Advanced Materials

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Tuning the electrostatics of ethylene-glycol-based self-assembled monolayers (SAMs) by doping with ions is shown. Molecular dynamics simulations unravel binding mechanisms and predict dipole strengths of the doped layers. Additionally, by applying such layers as dielectrics in organic thin-film transistors, the incorporated ions are proven to enhance device performance by lowering the threshold voltage and increasing conductivity.

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Recognition of Cations by Self-Assembled Monolayers of Crown Ethers

Cited by 99 publications

References 17 publications

Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit

Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit

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

Improving the Performance of Organic Thin‐Film Transistors by Ion Doping of Ethylene‐Glycol‐Based Self‐Assembled Monolayer Hybrid Dielectrics

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