Using hydrogen bonding-specific interactions to detect water in aprotic solvents at concentrations below 50ppm

Pinheiro, Carlos; Lima, João Carlos

doi:10.1016/j.snb.2005.08.013

Cited by 61 publications

(28 citation statements)

References 30 publications

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“…Blandamer et al [50] as well as Toma and Takasugi [51] observed that solvent polarity has a drastic effect on the electronic spectra of prentacyanoferrate (II) complexes bearing pyridine-based ligands. Pinheiro et al [52] studied an intensely solvatochromic pentacyano ruthenium(II) complex with a 2,2 -bipyridine ligand and exploited its particularly high sensitivity to traces of water for its detection in aprotic solvents using merely UV-Vis spectrophotometry [47]. Dyes of this family have been used as solvatochromic probes [53,54].…”

Section: Solvatochromic Complexes Involving Monoquats As Ligandsmentioning

confidence: 99%

Mono- and Di-Quaternized 4,4′-Bipyridine Derivatives as Key Building Blocks for Medium- and Environment-Responsive Compounds and Materials

Papadakis

2019

Molecules

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Mono-and di-quaternized 4,4 -bipyridine derivatives constitute a family of heterocyclic compounds, which in recent years have been employed in numerous applications. These applications correspond to various disciplines of research and technology. In their majority, two key features of these 4,4 -bipyridine-based derivatives are exploited: their redox activity and their electrochromic aptitude. Contemporary materials and compounds encompassing these skeletons as building blocks are often characterized as multifunctional, as their presence often gives rise to interesting phenomena, e.g., various types of chromism. This research trend is acknowledged, and, in this review article, recent examples of multifunctional chromic materials/compounds of this class are presented. Emphasis is placed on solvent-/medium-and environment-responsive 4,4 -bipyridine derivatives. Two important classes of 4,4 -bipyridine-based products with solvatochromic and/or environment-responsive character are reviewed: viologens (i.e., N,N -disubstituted derivatives) and monoquats (i.e., monosubstituted 4,4 -bipyridine derivatives). The multifunctional nature of these derivatives is analyzed and structure-property relations are discussed in connection to the role of these derivatives in various novel applications.Molecules 2020, 25, 1 2 of 30 recent) underlining the high versatility of this class of compounds [9,10,[12][13][14][15]. Perhaps, the most reviewed subject regarding the viologens is their electrochromism [13,14,16]. Viologens are known to undergo one-electron reductions electrochemically ( Figure 2) yielding colorful radicals i.e., cations that are stable in the absence of O 2 . Yet, their chromism can also be triggered through various stimuli (including light, heat, solvents, presence of various chemical species, pressure, etc.). All these possibilities shape the very versatile "chromic character" of viologens and generally of 4,4 -bipyridine derivatives. Even though this "chromic character" has only recently started gaining more attention and there is an increasing number of research articles emphasizing on the alternative uses of 4,4 -bipyridine derivatives, there are no reviews in this growing area up until now. Such an attempt is presented in this review paper with an emphasis on medium-and environment-responsive compounds and materials based on 4,4 -bipyridine. Primary focus is placed on viologen-involving solvatochromic systems as well as materials and compounds of this class whose chromic behavior is dependent on various environment stimuli. Molecules 2018, 23, x 2 of 30 Figure 2. Schemes depicting (a) the electrochromic cycle (1) and (b) the photochromic cycle of paraquat (A, counter anion). Structure and Properties of Viologens The Strong Electron-Withdrawing Character of ViologensThe strong electron-withdrawing character of viologens has been widely exploited in numerous molecular architectures and materials. Viologens can undergo reversible one-electron reductions forming radical cations (Figure 2a), which are vividly colo...

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Section: Solvatochromic Complexes Involving Monoquats As Ligandsmentioning

confidence: 99%

Mono- and Di-Quaternized 4,4′-Bipyridine Derivatives as Key Building Blocks for Medium- and Environment-Responsive Compounds and Materials

Papadakis

2019

Molecules

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“…For example, toluene as a solvent is widely used in the reaction of raw materials in medicine, pesticides, explosives, additives, spices, synthetic resins, and the production of polyester and other fine chemicals . Also, in the synthetic materials industry, toluene can be oxidized and sulfonated and undergo nitrification and disproportionation reactions and side‐chain chlorination reactions . In the process of preparing toluene, even after the distillation of the product, a small amount of water and other impurities still exist, although purity is increasingly in high demand, and sometimes, even a moisture content of less than 100 ppm is needed; with other organic solvents, fuels also have the same requirements, so the development of simple, effective, environmentally friendly, new organic solvent dehydration materials would be socially and economically valuable.…”

Section: Introductionmentioning

confidence: 99%

Polymeric‐hydrogel‐coated iron oxide magnetic particles for efficient solvent dehydration

Zhu

et al. 2018

J of Applied Polymer Sci

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In this article, we report the synthesis of crosslinked polyacrylamide-hydrogel-coated iron oxide (Fe 3 O 4 -PAM) magnetic nanoparticles as a kind of novel and efficient solvent-dehydrating agent. With the use of commercially available toluene (containing trace water at 168-173 ppm) as a model organic solvent, an excellent dehydration performance of Fe 3 O 4 -PAM was observed; trace water as low as 48 ppm was efficiently removed, and this desiccant could compete with respect to the dehydration efficiency with common sodium treatments. To our knowledge, this is the first example of the application of such water-swollen hydrogel-coated Fe 3 O 4 magnetic nanoparticles for the efficient removal of trace water in solvents. Also, the Fe 3 O 4 -PAM magnetic nanoparticles could be easily separated from the solvents after the dehydration treatment; thus, they possess a great advantage over traditional organic solvent dry methods and may find a variety of applications, for example, in oil dehydration and organic solvent drying.

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“…These sensors make possible in situ analysis of water content in organic solvents with high sensitivity and precision and low detection limits. Their applicability in water determination results from the fact that the addition of water into an organic solvent leads to the changes in intensities of their emission or absorption spectra and/or the spectral shifts of the sensors (Langhals 1990 ; Pinheiro et al 2006 ; Cha et al 2011 ; Rananaware et al 2015a , b ; Jung et al 2016 ). Some examples of these compounds, as well as the mechanism of their action have been freshly described by Jung et al ( 2016 ).…”

Section: Introductionmentioning

confidence: 99%

The application of 7H-indolo[1,2-a]quinolinium merocyanine as a new water sensor in organic solvents

Sawicka

Wróblewska

2017

Chem. Pap.

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The 7H-indolo[1,2-a]quinolinium merocyanine was applied as a new water sensor in organic solvents such as ethanol, propane-1-ol, propane-2-ol, DMSO, and DMF. The spectral changes of the dye caused by the addition of increasing amount of water into an organic solvent were investigated. Based on the results, the calibration curves were found as a relation between the position of the absorption band of the dye and the water concentration ranging from about 0.05 to 11% (w/w). In case of ethanol, propane-1-ol and propane-2-ol the plots were linear, whereas in DMSO and DMF, better results were obtained with the use of a polynomial function. The method allowed to determine the water content in a fast and precise manner.Graphical Abstract Electronic supplementary materialThe online version of this article (10.1007/s11696-017-0328-z) contains supplementary material, which is available to authorized users.

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Using hydrogen bonding-specific interactions to detect water in aprotic solvents at concentrations below 50ppm

Cited by 61 publications

References 30 publications

Mono- and Di-Quaternized 4,4′-Bipyridine Derivatives as Key Building Blocks for Medium- and Environment-Responsive Compounds and Materials

Mono- and Di-Quaternized 4,4′-Bipyridine Derivatives as Key Building Blocks for Medium- and Environment-Responsive Compounds and Materials

Polymeric‐hydrogel‐coated iron oxide magnetic particles for efficient solvent dehydration

The application of 7H-indolo[1,2-a]quinolinium merocyanine as a new water sensor in organic solvents

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