Rational Design of a Chromo- and Fluorogenic Hybrid Chemosensor Material for the Detection of Long-Chain Carboxylates

Descalzo, Ana B.; Rurack, Knut; Weißhoff, Hardy; Martínez‐Máñez, Ramón; Marcos, M. Dolores; Amorós, Pedro; Hoffmann, Katrin; Soto, Juán

doi:10.1021/ja045683n

Cited by 251 publications

(113 citation statements)

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“…For instance, the blending of models related to chemical sensors and inorganic systems has recently resulted in the preparation of hybrid organic-inorganic materials with enhanced patterns of selectivity. [8][9][10][11][12][13][14][15] In the course of this research we have focused our attention on one type of anion of critical environmental concern, [16][17][18] that is, the anionic surfactants. Surfactants are water-soluble surface-active agents comprised of a hydrophobic portion (a long alkyl chain) attached to a hydrophilic (water-soluble) moiety.…”

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A Simple Approach for the Selective and Sensitive Colorimetric Detection of Anionic Surfactants in Water

et al. 2007

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Since the formulation of supramolecular principles, chemists have been developing systems with enhanced functionalities.[1] More recently, the combination of chemical principles and solid structures has led to new synergic strategies, which embrace unprecedented tunability of the properties of the nanoscopic solids and new perspectives of applicability to supramolecular concepts. [2][3][4][5][6][7] We believe that one field in which these ideas might have a considerable impact is in the development of new chemical signaling protocols. For instance, the blending of models related to chemical sensors and inorganic systems has recently resulted in the preparation of hybrid organic-inorganic materials with enhanced patterns of selectivity. [8][9][10][11][12][13][14][15] In the course of this research we have focused our attention on one type of anion of critical environmental concern, [16][17][18] that is, the anionic surfactants. Surfactants are water-soluble surface-active agents comprised of a hydrophobic portion (a long alkyl chain) attached to a hydrophilic (water-soluble) moiety. Anionic surfactants are of widespread importance in the detergent industry, emulsification, lubrication, catalysis, and so on, and are widely employed. As a result of their anthropogenic origin and extensive use, it is a frequent task to determine surfactants in product formulations and in industrial samples for quality and process control. [19][20][21][22][23] Apart from the efforts in studying methods to reduce their environmental impact, another important aspect is the development of new and improved sensing methods for their determination. Many well-known methodologies require tedious procedures (for example, liquid and gas chromatography) or the use of relatively large amounts of chlorinated solvents that are not readily biodegradable (such as chloroform in the spectroscopic "methylene blue" method), [24] in addition to the fact that these methods cannot usually be used for in situ determinations. A different approach makes use of ion-selective electrodes; however, these still show limitations in their applicability, most commonly related to reproducibility and signal stability. [25][26][27][28][29][30] As a result of these restrictions, there is a real need to develop new methods for anionic surfactant sensing in water that are applicable to a wide range of situations. In this sense, novel selective and sensitive chromo-or fluorogenic methodologies are especially appealing for the design of simple in situ screening applications.As a part of our interest in the development of new chromofluorogenic sensing protocols for target guests, [31][32][33][34][35][36] herein we report a conceptually novel colorimetric method for the selective determination of anionic surfactants based on the use of imidazolium-containing ionic liquids on a solid support. [37][38][39] For this purpose, we have designed and prepared the hybrid system S1 (see Figure 1), which was used in a two-step sensing protocol. In the first step, the contact of S1 with a...

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A Simple Approach for the Selective and Sensitive Colorimetric Detection of Anionic Surfactants in Water

et al. 2007

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“…− [23,70,71]. These observations suggest that the fluoride anion and urea protons form N-H···F − hydrogen bonds at low concentrations of F − , while at higher concentrations of F − , deprotonation of Hb occurs.…”

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Recognition and sensing of anions through synergistic effects using simple benzimidazolium-urea receptors

Dong

Gao

2012

Chin. Sci. Bull.

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“…In this case, the mesoporous MCM-41 support was functionalised with a urea-phenoxazinone derivative that acted as both an anion receptor (through interaction of the urea group with the carboxylate head group of the fatty acids) and signalling unit (through colour and fluorescence changes, including fluorescence enhancement upon carboxylate binding). 16 Additionally, the inner walls of the pores were further functionalised with trimethylsilane in order to obtain a hydrophobic environment around the urea-phenoxazinone moiety. This solid displayed a remarkably selective response to fatty (long-chain) carboxylates.…”

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Mimicking tricks from nature with sensory organic–inorganic hybrid materials

et al. 2011

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Design strategies for (bio)chemical systems that are inspired by nature's accomplishments in system design and operation on various levels of complexity are increasingly gaining in importance. Within the broad field of biomimetic chemistry, this article highlights various attempts toward improved and sophisticated sensory materials that rely on the combination of supramolecular (bio)chemical recognition principles and nanoscopic solid structures. Examples range from more established concepts such as hybrid sensing ensembles with improved sensitivity and selectivity or for target analytes for which selectivity is hard to achieve by conventional methods, which were often inspired by protein binding pockets or ion channels in membranes, to very recent approaches relying on target-gated amplified signalling with functionalised mesoporous inorganic supports and the integration of native biological sensory species such as transmembrane proteins in spherically supported bilayer membranes. Besides obvious mimicry of recognition-based processes, selected approaches toward chemical transduction junctions utilizing artificially organized synapses, hybrid ensembles for improved antibody generation and uniquely colour changing systems are discussed. All of these strategies open up exciting new prospects for the development of sensing concepts and sensory devices at the interface of nanotechnology, smart materials and supramolecular (bio)chemistry.

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Rational Design of a Chromo- and Fluorogenic Hybrid Chemosensor Material for the Detection of Long-Chain Carboxylates

Cited by 251 publications

References 107 publications

A Simple Approach for the Selective and Sensitive Colorimetric Detection of Anionic Surfactants in Water

A Simple Approach for the Selective and Sensitive Colorimetric Detection of Anionic Surfactants in Water

Recognition and sensing of anions through synergistic effects using simple benzimidazolium-urea receptors

Mimicking tricks from nature with sensory organic–inorganic hybrid materials

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