Cinzia Chiappe

Cinzia Chiappe
Università di Pisa | UNIPI · Department of Pharmacy

Ph.D.

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299
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Publications

Publications (299)
Article
Full-text available
Cannabis sativa L. is a multi-purpose crop, whose resilience, adaptability and soil-enriching properties make it a low-impact production. In the last years, the cultivation of the “industrial” hemp varieties (THC < 0.2%) has been promoted by many Countries, opening a whole new market of hemp-derived products, such as its essential oil (EO). Its dis...
Article
Developing new materials for the separation of gas mixtures is a key subject in setting up a circular economy. In this work, we report the synthesis and application of novel polymeric membranes, based on polymerized ionic liquids (PILs), to be used for CO2 separation from different gas pairs. Phosphonium-based PILs have been copolymerized within an...
Article
Full-text available
Chiral ionic liquids CILs, or ionic liquids ILs with chiral additives, look very attractive chiral media for enantioselective electroanalysis, on account of their high chiral structural order at the electrochemical interphase. A family is now introduced of molecular salts with CIL properties, based on the chiral steroid building block of deoxycholi...
Article
A panel of ionic liquids has been synthesized and their effect on the vanadyl acetylacetonate solubility in acetonitrile has been firstly assessed. 1-Butyl-3-methylimidazolium acetate showed an unprecedented result, increasing the VO(acac)2 solubility in acetonitrile of more than one magnitude order (from 0.06 M to 1.1 M) opening new interesting ho...
Article
Full-text available
Four divalent ionic liquids based on imidazolium cations with alkyl or ether functionalized side-chains were synthesised and characterized: 3,3'-(tetraethyleneglycol-1,11-diyl)bis(1-methyl-1H-imidazolium)bromide, [tetraEG(mim)2][Br]2, 3,3'-(tetraethyleneglycol-1,11-diyl)bis(1-methyl-1H-imidazolium)acetate, [tetraEG(mim)2][OAc]2, 1-butyl-3-methylimi...
Article
Three novel deep eutectic solvents (DESs) were prepared with choline acetate (ChOAc) as the hydrogen bond acceptor (HBA) and three hydrogen bond donors (HBD): glycolic acid (GlyA), levulinic acid (LevA) and imidazole (Im). They showed different, albeit remarkable capabilities of dissolving lignin (from 35% to 100%) and hemicellulose (from 40% to 50...
Article
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An amendment to this paper has been published and can be accessed via a link at the top of the paper.
Article
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This study reports an ionic liquid (IL) promoted green method to obtain diaryl thioethers useful as key intermediates for the synthesis of matrix metalloproteinase (MMP) inhibitors. The synthetic pathway includes a sequential Ullmann reaction and Suzuki cross-coupling. The Ullmann conditions were optimized as regards the catalyst, the ionic liquid,...
Article
Full-text available
The preparation of Fe-decorated sporopollenins was achieved using pollen grains and an ionic liquid as solvent and functionalizing agent. The integrity of the organic capsules was ascertained through scanning electron microscopy studies. The presence of Fe in the capsule was investigated using FT-IR, X-ray photoemission spectroscopy and energy-disp...
Article
Full-text available
This paper reports the results of a spectroscopic study on the chemistry of some small papyrus fragments arising from three Egyptian excavation sites. The aim of this investigation was to verify the possibility to identify significant differences in ancient Egyptian papyri using noninvasive analytical methods, that is, ATR (attenuated total reflect...
Article
The cycloaddition of CO2 to epoxides has attracted a great deal of interest in recent years as an atom efficient way to employ this greenhouse gas as a useful C1 building block. While several ionic liquids have been tested as catalysts for the reaction, little attention has been devoted to dicationic ionic liquids (DILs). Herein, the catalytic acti...
Article
Ionic liquids (ILs) are neoteric solvents characterized by unique physicochemical properties and considerable structural variability. The thermal behavior of 24 ILs, belonging to two structurally related families with either bromide or Tf2N as counteranion, was analyzed. For bromide mono- and dicationic ionic liquids (DILs), thermal gravimetric ana...
Article
Full-text available
New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were...
Article
Full-text available
Dicationic ionic liquids (DILs) are a subclass of the ionic liquid (IL) family and are characterized by two cationic head groups linked by means of a spacer. While DILs are increasingly attracting interest due to their peculiar physico-chemical properties, there is still a lack of understanding of their intermolecular interactions. Herein, we repor...
Article
Full-text available
Carba analogues of biologically relevant natural carbohydrates are promising structures for the development of future drugs endowed with enhanced hydrolytic stability. An open synthetic challenge in this field is the optimization of new methodologies for the stereo-and regioselective opening of α-gluco carbasugar 1,2-epoxides that allow for the pre...
Article
Novel ammonium, phosphonium and imidazolium ionic liquids (ILs) based on levulinic acid as the anion were prepared and characterized (NMR, FT-IR, TGA, viscosity). Commercial methyl carbonate precursors were employed to access the target levulinate ILs through a quick, one-step synthetic procedure that does not require the use of halogenated solvent...
Article
Nine structurally-related fatty acid ionic liquids have been prepared and their thermal behavior as well as their ability to self-assemble in water has been investigated. The thermal properties were studied by thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC), while the aggregation behavior was analyzed by tensiometry,...
Article
In order to identify most suitable ionic liquids (ILs) for potential applications in infection prevention and control, in the present study we comparatively evaluated the antimicrobial potency and hemolytic activity of 15 ILs, including 11 previously described and four newly synthesized ILs, using standard microbiological procedures against Gram-po...
Article
Developing effective strategies to increase the chemical stability and to fine tune the physico‐chemical properties of melanin biopolymers by rational control of π‐electron conjugation is an important goal in materials science for biomedical and technological applications. Herein we report that poly‐1,8‐dihydroxynaphthalene (pDHN), a non‐nitrogenou...
Article
Nanoscale disassembly of mussel-inspired polydopamine (PDA) in ionicliquids (ILs) was recently shown to induce an electron paramagnetic resonance (EPR)-detectable reorganization of free radical centers in the resulting nanoparticles (NPs) in an IL-controlled manner. Herein, we report electrical impedance spectroscopy (EIS) data showing that PDA NPs...
Article
Vanadium redox flow battery (VRFB) is one of the most promising large-scale energy storage system; however, a widespread VRFB development is still limited by the poor electrochemical activity of graphite electrodes and a poor understanding of redox reactions occurring at electrode/electrolyte interface. In this work, DFT was performed to study the...
Article
Vanadium redox flow battery(VRFB) is one of the most promising large- scale energy storage system; however, a wide spread VRFB development is still limited by the poor electrochemical activity of graphite electrodes and a poor understanding of redox reactions occurring at electrode /electrolyte interface. In this work, DFT was performed to study th...
Article
Two new levulinate-based protic ionic liquids (Lev PILs) have been synthetized through an easy, scalable neutralization reaction between levulinic acid (LA), which is one of the most promising renewable building blocks obtainable from cellulose, and amidine superbases (either DBU or DBN). The prepared PILs have been characterized (by means of NMR,...
Article
Full-text available
Selective and potent MMP‐12 inhibitors endowed with improved hydrophilicity are highly sought for a potential use in the treatment of lung and cardiovascular diseases. In the present paper, we modified the structure of a nanomolar MMP‐12 inhibitor (1) in order to incorporate an ionic liquid (IL) moiety able to improve its water solubility. Four bio...
Article
Full-text available
Dicationic ionic liquids (DILs), a subset of the ionic liquid (IL) family, have attracted growing interest in recent years, and the range of applications within which they are investigated is constantly expanding. However, data which allows structure to property correlation of a DIL is still limited, and thus selecting an appropriate salt to addres...
Article
In spite of the increasing fundamental and practical interest of electrochemistry in ionic liquids (ILs), exploration of chiral ionic liquids (CILs) in view of enantioselective electrochemistry and electroanalysis is surprisingly overdue. In this study a family of chiral ionic liquids (CILs) based on natural chiral building blocks, of easy synthesi...
Article
A family of structurally-related guanidinium bistriflimide ionic liquids has been prepared and characterized. TGA analyses showed a high thermal stability for all the proposed ionic liquids while DSC and XPS analyses divided them into distinct subsets depending on whether one or more constraining cycles were present. The results obtained highlighte...
Poster
Full-text available
Vanadium redox flow battery (VRFB) is one of the most promising large-scale energy storage system; however, a widespread VRFB development is still limited by the poor electrochemical activity of graphite electrodes and a poor understanding of redox reactions occurring at electrode/electrolyte interface. In this work, DFT was performed to study the...
Article
Full-text available
Some clusters of Reichardt’s dye with two ion pairs have been studied at the TD-DFT level in order to understand the effect of the ionic liquid anion on solvatochromism. Coherently with the experimental data, the anion effect results substantially related to the anion size, although generally less important than the cation effect. Only small anions...
Article
Full-text available
Supported chiral ionic liquids (SILs) were prepared choosing the starting material for the ionic liquid part from the enantiopure stock of the chiral pool (monoterpenoids and an amino acid) and the sporopollenin as an environmentally friendly support. Sporopollenins are microcapsules with naturally well-defined sizes and shapes that can be obtained...
Article
The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture of (Z)-3-alkylideneisobenzofuran-1(3H)-ones (from 5-exo-dig cyclization) and 1H-isochromen-1-ones (from 6-e...
Conference Paper
Vanadium redox flow battery (VRFBs) is one of the most promising large-scale energy storage systems; however, a widespread VRFB development is still limited by the poor electrochemical activity of the graphite electrode and a poor understanding of redox reactions occurring at electrode/electrolyte interfaces. In this work, DFT were performed to stu...
Article
The authors report the first modification of ionic liquids with metal carbamates. A selection of homoleptic N,N-dialkylcarbamates carbamates of groups 4 and 5 metals, M(O2CNR2)n, were dissolved in bis(trifluoromethylsulfonyl)imide-based ionic liquids, i.e. [bmim][Tf2N] and [P(oct)4][Tf2N], at 291 K. The resulting solutions were characterized by mea...
Article
Mixtures of ionic liquids (ILs) having a common ion but differing in the identity of the anion or cation represent highly interesting media. By varying the composition, one can successfully modulate specific physicochemical, structural, and biological properties. The molecular interactions (coulombic, hydrogen-bonding, van der Waals, and π-π interm...
Article
The conversion of cellulose into target chemicals is essential for the development of the sustainable chemical industry of the future. To this end, the single step transformation of cellulose into levulinic acid (LA) has been investigated in different aqueous systems and using either Brønsted acidic ILs, metal salts, or a mixture of these as cataly...
Article
The aim of this paper was to synthesize ionic liquids (ILs) that can play the double role of capping and reducing agents for the fabrication of silver nanoparticles (Ag NPs). A new simple method of synthesis of some ILs that have as counter ion citrate and their application in silver and gold nanoparticles preparation will be presented. AgNPs with...
Article
This paper deals with the concept of process intensification applied to the extraction of essential oil (EO). Microwave hydrodistillation (MWHD) and simultaneous ultrasound MW-assisted hydrodistillation (US-MWHD) were intensified by coupling them with a green tool: ionic liquids (ILs). The yield and chemical composition of the cumin EO obtained by...
Article
The regiochemical outcome of the iodolactonization of 2-alkynylbenzoic acids, carried out at 100 °C in ionic liquids (ILs) as unconventional solvents and with molecular iodine as the iodine source, in the absence of external bases, was found to be strongly dependent on the nature of the IL medium. In particular, while the use of N-ethyl-N-methylmor...
Article
The development of bio-based ionic liquids (ILs) has attracted a great deal of interest in recent years. The so called long chain fatty acid ionic liquids (LCFA-ILs) represent a bio-based subfamily of the hydrophobic ionic liquids. Here, a new preparation of the three major classes of LCFA-ILs (phosphonium, ammonium, imidazolium) is presented with...
Article
Full-text available
Economical and environmental concerns are the main motivations for development of energy-efficient processes and new eco-friendly materials for the capture of greenhouse gases. Currently, H2S capture is dominated by physical and/or chemical absorption technologies, which are, however, energy intensive and often problematic from an environmental poi...
Article
Hydrolysis and subsequent degradation of microcrystalline cellulose in five ionic liquids (ILs) using metal salts and/or Brønsted acids as catalysts allowed for the direct access to 5-hydroxymethylfurfural (HMF), an important renewable biofuel precursor and a useful building-block. For each catalytic system, several reaction parameters (temperature...
Article
Unreported ureido cross-linked chitosans were obtained employing the CO2-chitosan-ionic liquid three component system. Under the conditions used, the greenhouse gas functions as a safe cross-linking agent of the biopolymer thanks to the solvent-catalytic effect of [bmim][OAc].
Article
A systematic study on the viscosity and refractive index of 1-alkyl-3-methylimidazolium based ionic liquids (alkyl = methyl, butyl and hexyl) combined with three phosphorus containing anions, i.e. dimethylphosphate, methyl methylphosphonate and methylphosphonate, is reported. Experimental measurements account for temperature effects, while the refr...
Article
Thermally stable amidinium/guanidinium N,N-dialkylcarbamates, including vacuum stable compounds, have been prepared, and then isolated in the solid state, by reaction of tetramethylguanidine (TMG) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with secondary amines under atmospheric pressure of CO2. The same method has been successfully applied to α-a...
Article
The cycloisomerization of readily available 2-alkynylbenzamides has been conveniently carried out with CuCl2 as catalyst under basic conditions in 1-ethyl-3-methylimidazolium ethyl sulfate (EmimEtSO4) as an unconventional solvent. The process leads to (Z)-3-alkylideneisoindolin-1-ones in a chemo-, regio-, and stereoselective manner. The catalyst/so...
Article
Full-text available
A chiral ionic liquid with a natural alcohol based chain was used as a tailoring agent for the synthesis of simple and cost effective materials such as ZnO, CuO, CuO–ZnO with peculiar morphology. The morphology and chemical composition of the microstructures were investigated by bright-field and scanning transmission microscopy (BF-TEM and STEM), e...
Article
Full-text available
Among the alternative mineral tanning agents investigated for replacing chromium, titanium (IV)-based salts are one of the most promising ones for the development of novel and cleaner tanning processes in the leather industry. The molecular mechanism of the solvation of titanyl salts and their interaction with masking agents was investigated in the...
Article
The effect of the addition of four different halide-free ionic liquids (ILs) during the maceration step on Foeniculum vulgare essential oil (EO) extraction by hydrodistillation was investigated. The EO yields and their chemical composition were also evaluated, as well as the possibility of reusing the IL aqueous solutions. Although all the investig...
Chapter
Economical and environmental concerns are the main motivations for development of energy-efficient processes and new eco-friendly materials for the capture of greenhouse gases. Currently, H2S capture is dominated by physical and/ or chemical absorption technologies, which are, however, energy intensive and often problematic from an environmental po...
Article
The reaction paths and the intermediate structures related to the formation of the Breslow intermediate and its oxidation along the oxidative/oxygenative lanes have been studied from a mechanistic point of view, with the support of gas phase and computational studies. The results confirm the occurrence of a single electron transfer from the Breslow...
Article
Ionic liquids (ILs) are considered as a promising class of potentially environmentally-friendly solvents for use in a variety of applications. However, they are generally synthesized by batch in non-sustainable solvents. Actually, ILs to be really “green” compounds for widespread use should be also synthesized in a benign manner. Here, we report an...
Article
Despite the growing scientific and technological relevance of polydopamine (PDA), a eumelanin-like adhesive material widely used for surface functionalization and coating, knowledge of its structural and physicochemical properties, including in particular the origin of paramagnetic behavior, is still far from being complete. Herein, we disclose the...
Article
The aim of this study was to verify the effect of several cyclic onium based ionic liquids (ILs), including mono- and dicationic derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO), a dialkyl morpholinium salt and a Brønsted acidic IL, as enhancers of the in vitro transdermal permeation and skin retention of diltiazem through and into hairless rat...
Article
Full-text available
A convenient carbonylative approach to 2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO₄) as the solvent is presented. It is based on the sequential concatenation of two catalytic cycles, both catalyzed by the same metal species (auto-tandem catalysis): the first cycle corresponds to...
Poster
Full-text available
In the last fifteen years, ionic liquids (ILs) have generated an increasing interest and have been proposed as alternative solvents, components or additives in a wide and diversified range of applications. There are indeed several important properties, which make ILs attractive in academic as well as in industrial fields. In particular, ILs are cla...
Article
The effect of addition of dimethylimidazolium dimethylphosphate in the maceration step, which precedes hydrodistillation, on yield and composition of the essential oil of cinnamon dried bark and cortex has been evaluated. The use of a 1:1 ionic liquid (IL)-water mixture permitted the improvement of the essential oil yield by about 200%. Moreover, a...
Poster
Full-text available
In the last fifteen years, ionic liquids (ILs) have attracted considerable attention. Through continuous efforts of numerous researchers, ILs have achieved not only a consolidated popularity as “green” solvents for synthesis and extraction processes, but also as powerful catalysts, electrolytes, precursors or additives to employ in several of areas...
Article
Chiral ionic liquids (CILs) have been obtained in high yield using commercial propylene oxide or natural alcohols (citronellol and nopol) as building blocks. The self-assembly ability at the interface IL/air for some couples of enantiopure and racemic CILs was explored by angle resolved XPS.
Article
There are still constraints to algae-sourced biodiesel commercialization owing to the high cost and energy consumption of biomass cultivation and lipid extraction. The use of "low-cost" protic ILs based on tetramethylguanidinium and 1,8-diazabicyclo[5.4.0]undec-7-ene cations (some of them generated in situ by reaction of the corresponding bases wit...
Article
We report a green, facile chemical approach to isolate sporopollenin capsules from pollen grains based on the use of ionic liquids (ILs). Depending on the IL structure, it is possible to remove proteins and the cellulose-rich cell wall (intine) assuring grain integrity and simultaneously obtaining a direct functionalization of the sporopollenin.
Article
Full-text available
Vegetable oils and fatty acid esters are suitable precursor molecules for the production of a variety of bio-based products and materials, such as paints and coatings, plastics, soaps, lubricants, cosmetics, pharmaceuticals, printing inks, surfactants, and biofuels. Here, we report the possibility of using Lewis acidic ionic liquids (ILs) to obtain...
Article
The effect of addition of ionic liquids (ILs) during hydrodistillation of the essential oil of Rosmarinus officinalis L. on its yields has been evaluated. Four different chloride based ILs have been used, namely a hydroxyl functionalized imidazolium salt, (1-hydroxyethyl-3-methyl imidazolium chloride (IL-1), a morpholinium salt, (N,N-butylmethylmor...
Article
Owing to economic reasons, the textile dyeing industry generally employs traditional and absolutely no-eco-friendly processes: very large quantities of water are indeed required together with a large number of added chemicals which represent dramatic environmental issues. In order to improve the sustainability of the process, we have investigated t...
Article
Conventional chrome-tanning process is constantly under pressure from increasingly stringent environmental regulations on discharges of chromium-containing effluents and wastes. For this reason, in the past years alternative chrome-free tanning processes have been developed. Among these, titanium tanning is one of the most promising substitutes for...
Article
Despite the weakly coordinating ability of the bis-(trifluoromethylsulfonyl)imide anion ([Tf2N]-) the corresponding ionic liquids (ILs) are able to dissolve relevant amounts of metal salts having the same anion, M[Tf2N]x. To better understanding the metal dissolution process we evaluated the interaction ability of a set of metal cations (Y(III), Al...