New Colorimetric and Fluorometric Chemosensor Based on a Cationic Polythiophene Derivative for Iodide-Specific Detection

Ho, Hoang A; Leclerc, Mario

doi:10.1021/ja028765p

Cited by 287 publications

(213 citation statements)

References 17 publications

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“…Amongst the plethora of biologically and medically relevant anions, the recognition and sensing of iodide in water is of interest both due to its crucial role in hormone biosynthesis by the thyroid gland11, 12 and its use in contrast media for radiographic imaging applications 13. Examples of anion hosts capable of sensing iodide by optical methods are scarce,14–17 and to the best of our knowledge, the use of molecular‐anion receptors for the host–guest recognition and sensing of iodide in water is unprecedented.…”

Section: Introductionmentioning

confidence: 99%

Iodide Recognition and Sensing in Water by a Halogen‐Bonding Ruthenium(II)‐Based Rotaxane

Langton

Marques

Robinson

et al. 2015

Chemistry A European J

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The synthesis and anion‐recognition properties of the first halogen‐bonding rotaxane host to sense anions in water is described. The rotaxane features a halogen‐bonding axle component, which is stoppered with water‐solubilizing permethylated β‐cyclodextrin motifs, and a luminescent tris(bipyridine)ruthenium(II)‐based macrocycle component. 1H NMR anion‐binding titrations in D2O reveal the halogen‐bonding rotaxane to bind iodide with high affinity and with selectively over the smaller halide anions and sulfate. The binding affinity trend was explained through molecular dynamics simulations and free‐energy calculations. Photo‐physical investigations demonstrate the ability of the interlocked halogen‐bonding host to sense iodide in water, through enhancement of the macrocycle component’s RuII metal–ligand charge transfer (MLCT) emission.

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Section: Introductionmentioning

confidence: 99%

Iodide Recognition and Sensing in Water by a Halogen‐Bonding Ruthenium(II)‐Based Rotaxane

Langton

Marques

Robinson

et al. 2015

Chemistry A European J

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“…7,8 Up to date, a variety of main-chain and side-chain PILs have been synthesized by chain-growth or step-growth polymerizations.1,9-12 Meanwhile, diverse types of synthetic polymers (e.g., polyimides, 11 polyolefins, 13,14 and conjugated polymers 15,16 ) have been integrated with ionic liquid groups for versatile uses.Polypeptides are mimics of natural peptides and able to form stable secondary structures (e.g., a-helices and b-sheets) in solution and solid state. [17][18][19] They are biocompatible and can be readily prepared in a large scale by ring-opening polymerization of N-carboxyanhydride (NCA) monomers.…”

mentioning

confidence: 99%

“…1,9-12 Meanwhile, diverse types of synthetic polymers (e.g., polyimides, 11 polyolefins, 13,14 and conjugated polymers 15,16 ) have been integrated with ionic liquid groups for versatile uses.…”

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confidence: 99%

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Polypeptide ionic liquid: Synthesis, characterization, and application in single‐walled carbon nanotube dispersion

Deng

Yuan

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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Polymer ionic liquids (PILs) are a type of polyelectrolytes containing ionic liquid species (e.g., imidazolium, pyridinium, hexafluorophosphate and triflates) in the main chain or the side chain.1 They have shown interesting physical properties, including conductivity and low glass transition temperature, which depends strongly on polymer primary and secondary structures, architectures, and so forth.2 Increasing attention has been paid for their potential applications in different fields, such as energy, 3,4 catalysis, 5,6 and biomedical applications. 7,8 Up to date, a variety of main-chain and side-chain PILs have been synthesized by chain-growth or step-growth polymerizations.1,9-12 Meanwhile, diverse types of synthetic polymers (e.g., polyimides, 11 polyolefins, 13,14 and conjugated polymers 15,16 ) have been integrated with ionic liquid groups for versatile uses.Polypeptides are mimics of natural peptides and able to form stable secondary structures (e.g., a-helices and b-sheets) in solution and solid state. [17][18][19] They are biocompatible and can be readily prepared in a large scale by ring-opening polymerization of N-carboxyanhydride (NCA) monomers. 20,21 When helical polypeptides conjugated with functional moieties (e.g., saccharide [22][23][24] and oligo-ethylene-glycol), 25,26 they demonstrated promising properties, such as molecular recognition and thermoresponsive property, which are associated with their unique spatial organization of surface moieties.Here, we report the design and synthesis of polypeptide ionic liquids and evaluation of their potential application for the dispersion of single-walled carbon nanotubes (SWCNTs), aiming to develop a new class of polymeric materials. These polypeptide ionic liquids adopt a-helical conformation in solid state and solution and show superior SWCNT dispersibility in water. To the best of our knowledge, this is the first example of polypeptide ionic liquid adopting a-helical conformation.c-Chloropropyl-L-glutamate-based N-carboxyanhydride (CP-NCA, 2, Supporting Information Fig. S1) was first synthesized in two steps from L-glutamic acid with an overall yield of 40-50% (Scheme 1). Typically, c-chloropropyl-L-glutamate (CP-Glu, 1) was synthesized by monoesterification of L-glutamic acid with 3-chloropropanol in the presence of sulfuric acid instead of chlorotrimethylsilane 22 at room temperature. Then, 1 was cyclized with triphosgene at room temperature in anhydrous THF to afford 2.A series of poly(c-chloropropyl-L-glutamate)s [PCPLGs, 3, Supporting Information Fig. S2(A)] with different number average molecular weights (M n s) and molecular weight distributions (PDIs) were then synthesized by ring-opening polymerization of CP-NCAs with different initial monomer to initiator (i.e., n-butylamine instead of hexamethyldisilazane 22 ) ratios or using triethylamine as the initiators to achieve the highest M n .27 The M n s of PCPLGs were revealed by gel permeation chromatography (GPC, Supporting Information Fig. S3). While we have attempted to prepare polypeptid...

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“…Over the past decades, conjugated polyelectrolytes (CPEs) have been widely used in sensing and cell imaging due to their intriguing optoelectronic and biocompatible properties [1][2][3][4][5][6]. Structurally, conjugated polyelectrolytes (CPEs) are fluorescent macromolecules with electron-delocalized backbone and water-soluble side chains which determine the main optical properties and capability to dissolve in water for their further biological applications respectively.…”

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confidence: 99%

Star-shaped conjugated oligoelectrolyte for bioimaging in living cells

et al. 2013

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A new star-shaped oligoelectrolyte (TEFCOONa) with triphenylamine as the core, acetylene as linkage and anionic fluorenes as arms was obtained and used for direct imaging in living PANC-1 cells. Because of the hydrophobic conjugated groups of the oligoelectrolyte, TEFCOONa can form nanospheres with an average diameter of ~75 nm in 10 mmol/L PBS. These nanospheres possess a relatively high absolute quantum yield (16.5% in PBS), low cytotoxicity and can penetrate into the nucleus through the cytoplasm, which is essential for living cellular imaging. Collectively, these results validate our rational design of conjugated oligoelectrolyte and even hyper branched polymers-copolyelectrolyte as effective nanovectors for bioimaging and other clinical applications.

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New Colorimetric and Fluorometric Chemosensor Based on a Cationic Polythiophene Derivative for Iodide-Specific Detection

Abstract: Electrostatic interactions between anions and a new water-soluble, cationic, affinitychromic poly(3-alkoxy-4-methylthiophene) derivative provide a new tool for a selective optical detection method (colorimetric or fluorometric) for iodide ions.

Cited by 287 publications

References 17 publications

Iodide Recognition and Sensing in Water by a Halogen‐Bonding Ruthenium(II)‐Based Rotaxane

Iodide Recognition and Sensing in Water by a Halogen‐Bonding Ruthenium(II)‐Based Rotaxane

Polypeptide ionic liquid: Synthesis, characterization, and application in single‐walled carbon nanotube dispersion

Star-shaped conjugated oligoelectrolyte for bioimaging in living cells

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