Quaternary Nitrogen Research Articles

Identification of organic nitrogen compounds in methanol-soluble portion from sweet sorghum stalk methanolysis

Understanding the chemical composition of organic nitrogen compounds (ONCs) in biomass and its derived liquids is important because of their negative impacts on the environment during biomass utilization as fuel. In this study, X-ray photoelectron spectrometer (XPS) was used to identify the nitrogen forms on sweet sorghum stalk (SSS) surface and gas chromatograph/mass spectrometer (GC/MS) together with electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometer (FTICRMS) were employed to analyze ONCs in methanol-soluble portion (MSP) from SSS methanolysis. Analysis with XPS shows that the nitrogen forms on SSS surface mainly include pyrrolic, amino, and quaternary nitrogen species. GC/MS identified 14 ONCs in MSP, including 3 pyrroles, 3 indoles, 2 imidazoles, 3-methoxypyridine, 1-(hex-5-enyl)-1-methylhydrazine, cyclohexanecarbohydrazide, N-pyridin-3-ylacetamide, 1,3,4-trimethyl-1H-pyrazol-5(4H)-one, and pyridin-3-amine. According to analysis with negative-ion ESI FTICRMS, N1On class species are the main neutral nitrogen compounds (NNCs) in MSP. N1O3 class species are the most abundant NNCs, followed by N1O4 and N1O5 class species. Pyrroles and indoles should be dominant NNCs based on double bond equivalent (DBE) distributions. In positive-ion mode, most of the detected basic nitrogen compounds in MSP are N2On class species, in which N2O2–N2O4 class species with DBE=8–12 and carbon atom numbers of 19–28 are the most abundant. N2On class species with DBE<4 are likely to be diamines, hydrazines, hydrazides, imidazoles, and/or pyrazoles, while those with DBE≥4 could be ascribed to pyridinamine, pyrazines, pyrimidines, benzoimidazoles, indazoles, and/or isoquinolinamines.

Effects of CO2 on the fuel nitrogen conversion during coal rapid pyrolysis

To investigate the fuel nitrogen conversion during rapid pyrolysis, the tests with Genesee bituminous coal and Petroleum coke were accomplished under N2 and CO2 atmosphere in a fixed bed reactor equipped with a Fourier transform infrared analyzer. The samples were analyzed by an X-ray photoelectron spectroscopy (XPS) to determine the fuel nitrogen conversion mechanism during rapid pyrolysis. Furthermore, the fuel nitrogen distribution in pyrolysis products were also calculated based on the testing results. It was found that higher temperature can enhance the conversion of fuel nitrogen in the char to both HCN and NH3. The effects of CO2 on coal pyrolysis depended heavily on the temperature of rapid pyrolysis. There were more quaternary nitrogen (N-Q) consumed during rapid pyrolysis in CO2 atmosphere than that in N2 atmosphere, causing more NH3 formation in CO2 atmosphere. Higher temperature can restrain the formation of N2 as a result of the generation of more H free radicals. Besides, NO was also one of the major products during coal rapid pyrolysis.

N2 plasma treatment on activated carbon fibers for toxic gas removal: Mechanism study by electrochemical investigation

The mechanisms of the SO2 adsorption properties of activated carbon fibers (ACFs) after plasma treatment were studied. The surfaces of the ACFs were modified by a plasma treatment using N2 gas to enhance the SO2 adsorption of the fibers based on the effects of introduced nitrogen functional groups, especially quaternary nitrogen groups. Through the comparative analysis of X-ray photoelectron spectroscopy (XPS), especially the N1s component and SO2 adsorption data, quaternary nitrogen groups were determined to be effectively introduced onto the surface of the ACFs. SO2 molecules have lone pair electrons and attach themselves to the ACFs’ pores as the concentration of quaternary nitrogen increases. However, the pyridine N-oxide (N-X) functional group exhibited acidic properties and had a neutralizing effect on the ACF surfaces, reducing the strength of electrostatic interactions with the SO2 molecules. These types of mechanisms are proved by various physicochemical and electrical characterizations, especially the SO2 sensing capability of plasma-treated ACFs. The reversible sensing indicates that N2 plasma treatment changed the electrical properties of the carbon sample, leading to an intriguing sensing mechanism.

Interpretation of X-ray photoelectron spectra of carbon-nitride thin films: New insights from in situ XPS

We report on angular-resolved x-ray photoelectron spectroscopy (XPS) studies of magnetron sputtered CNx thin films, first in situ (without air exposure), then after air exposure (for time periods ranging from minutes to several years), and finally after Ar ion etching using ion energies ranging from 500 eV to 4 keV. The as-deposited films typically exhibit two strong N1s peaks corresponding to pyridine-like, and graphite-like, at ∼398.2 eV and ∼400.7 eV, respectively. Comparison between in situ and air-exposed samples suggests that the peak component at ∼402–403 eV is due only to quaternary nitrogen and not oxidized nitrogen. Furthermore, peak components in the ∼399–400 eV range cannot only be ascribed to nitriles or pyrrolic nitrogen as is commonly done. We propose that it can also be due to a polarization shift in pyridinic N, induced by surface water or hydroxides. Argon ion etching readily removes surface oxygen, but results also in a strong preferential sputtering of nitrogen and can cause amorphization of the film surface. The best methods for evaluating and interpreting the CNx film structure and composition with ex-situ XPS are discussed.

N‐doped Carbon Nanotubes for the Oxygen Reduction Reaction in Alkaline Medium: Synergistic Relationship between Pyridinic and Quaternary Nitrogen

AbstractN‐doped carbon nanotubes (N‐CNTs) prepared using a sustainable methodology based on a ball milling process were applied as catalysts for Oxygen Reduction Reaction (ORR). From two different N‐doping methodologies using melamine and urea as N‐enriched precursors, resulted in N‐CNTs with surface areas in the range 350–364 m2 g−1, and surface nitrogen contents from 0.2 % to 4.8 %, corresponding to three N‐types: pyridinic, pyrrolic and quarternary. Irreversible cathodic peaks were observed in the cyclic voltammograms of all catalysts in the presence of an O2‐saturated KOH solution, proving their ORR electrocatalytic activity. Onset potentials (Eon) varied from −0.159 to −0.128 V for N‐CNTs, approaching that of Pt/C (−0.124 V). Furthermore, the two best catalysts also exhibited an average number of electrons transferred per O2 of 3.3 and 3.1 e, respectively. These results suggest an O2‐reduction mechanism which is half controlled by the indirect pathway and half determined by the direct pathway. Moreover, the best N‐CNT catalyst exhibited higher durability and methanol tolerance than Pt/C. The correlation between ORR performance data and N‐CNT catalyst composition suggests that the Npyridinic/Nquaternary ratio is more relevant role than the total N content. In fact, the catalysts with the best performance (in terms of Eon and nO2) exhibited the highest Npyridinic/Nquaternary ratio, 5.6 and 3.9 respectively, while their nitrogen contents were 3.1 and 0.8 %.

Interaction Induced High Catalytic Activities of CoO Nanoparticles Grown on Nitrogen-Doped Hollow Graphene Microspheres for Oxygen Reduction and Evolution Reactions.

Nitrogen doped graphene hollow microspheres (NGHSs) have been used as the supports for the growth of the CoO nanoparticles. The nitrogen doped structure favors the nucleation and growth of the CoO nanoparticles and the CoO nanoparticles are mostly anchored on the quaternary nitrogen doped sites of the NGHSs with good monodispersity since the higher electron density of the quaternary nitrogen favors the nucleation and growth of the CoO nanoparticles through its coordination and electrostatic interactions with the Co2+ ions. The resulting NGHSs supported CoO nanoparticles (CoO/NGHSs) are highly active for the oxygen reduction reaction (ORR) with activity and stability higher than the Pt/C and for the oxygen evolution reaction (OER) with activity and stability comparable to the most efficient catalysts reported to date. This indicates that the CoO/NGHSs could be used as efficient bi-functional catalysts for ORR and OER. Systematic analysis shows that the superior catalytic activities of the CoO/NGHSs for ORR and OER mainly originate from the nitrogen doped structure of the NGHSs, the small size of the CoO nanoparticles, the higher specific and electroactive surface area of the CoO/NGHSs, the good electric conductivity of the CoO/NGHSs, the strong interaction between the CoO nanoparticles and the NGHSs, etc.

Towards understanding the mechanism of action of antibacterial N-alkyl-3-hydroxypyridinium salts: Biological activities, molecular modeling and QSAR studies

In this study, we have carried out a combined experimental and computational investigation to elucidate several bred-in-the-bone ideas standing out in rational design of novel cationic surfactants as antibacterial agents. Five 3-hydroxypyridinium salts differing in the length of N-alkyl side chain have been synthesized, analyzed by high performance liquid chromatography, tested for in vitro activity against a panel of pathogenic bacterial and fungal strains, computationally modeled in water by a SCRF B3LYP/6-311++G(d,p) method, and evaluated by a systematic QSAR analysis. Given the results of this work, the hypothesis suggesting that higher positive charge of the quaternary nitrogen should increase antimicrobial efficacy can be rejected since 3-hydroxyl group does increase the positive charge on the nitrogen but, simultaneously, it significantly derogates the antimicrobial activity by lowering the lipophilicity and by escalating the desolvation energy of the compounds in comparison with non-hydroxylated analogues. Herein, the majority of the prepared 3-hydroxylated substances showed notably lower potency than the parent pyridinium structures, although compound 8 with C12 alkyl chain proved a distinctly better antimicrobial activity in submicromolar range. Focusing on this anomaly, we have made an effort to reveal the reason of the observed activity through a molecular dynamics simulation of the interaction between the bacterial membrane and compound 8 in GROMACS software.

Revealing the Origin of Activity in Nitrogen-Doped Nanocarbons towards Electrocatalytic Reduction of Carbon Dioxide.

Carbon nanotubes (CNTs) are functionalized with nitrogen atoms for reduction of carbon dioxide (CO2 ). The investigation explores the origin of the catalyst's activity and the role of nitrogen chemical states therein. The catalysts show excellent performances, with about 90 % current efficiency for CO formation and stability over 60 hours. The Tafel analyses and density functional theory calculations suggest that the reduction of CO2 proceeds through an initial rate-determining transfer of one electron to CO2 , which leads to the formation of carbon dioxide radical anion (CO2 (.-) ). The initial reduction barrier is too high on pristine CNTs, resulting in a very high overpotentials at which the hydrogen evolution reaction dominates over CO2 reduction. The doped nitrogen atoms stabilize the radical anion, thereby lowering the initial reduction barrier and improving the intrinsic activity. The most efficient nitrogen chemical state for this reaction is quaternary nitrogen, followed by pyridinic and pyrrolic nitrogen.

Highly active N-doped carbon nanotubes prepared by an easy ball milling method for advanced oxidation processes

The performance of novel N-doped carbon materials prepared by an easy ball milling method was evaluated in two distinct advanced oxidation processes (AOPs): catalytic wet air oxidation (CWAO) and catalytic ozonation (COZ), using oxalic acid as model pollutant. The ball milling method allows the incorporation of large amounts of N-groups onto the surface of carbon nanotubes, namely pyridine-like N atoms (N-6), pyrrole-like N atoms (N-5) and quaternary nitrogen (N-Q), resulting in highly active catalysts for the oxidation of oxalic acid by both AOPs. The material prepared by ball milling with melamine without solvent is the most promising sample, combining an easy preparation with high amount of N-functionalities. Under the operation conditions used, oxalic acid was completely mineralized in 5min by CWAO and in 4h by COZ. The novel metal-free catalyst developed by this easy ball milling method demonstrated to be effective, confirming that this solvent-free methodology is quite adequate for the preparation of N-doped carbon materials with enhanced properties for the mineralization of organic pollutants by the studied processes.

Nitrogen-containing chitosan-based carbon as an electrode material for high-performance supercapacitors

Nitrogen-containing activated carbons were prepared from chitosan, a widely available and inexpensive biopolysaccharide, by a simple procedure and tested as electrode material in supercapacitors. The physical activation of chitosan chars with CO2 led to carbons with a very high nitrogen content (up to 5.4 wt%) and moderate surface areas (1000–1100 m2 g−1). Only chitosan-based activated carbons with a similar microporous structure were considered in this study to evaluate the effect of the nitrogen content and distribution on their electrochemical performance. The N-containing activated carbons were tested in two- and three-electrode supercapacitors using an aqueous electrolyte (1 M H2SO4), and they exhibited superior surface capacitance (19.5 µF cm−2) and pseudocapacitance compared to a commercial activated carbon with a negligible nitrogen content and similar microporosity. The low oxygen content and the presence of stable quaternary nitrogen improved the charge propagation on the chitosan-based carbons, which was confirmed by the high capacity retention of 83 %. The chitosan-based carbons exhibited excellent cyclic stability and maintained 100 % of their capacitance after 5000 charge/discharge cycles at a current density of 1 A g−1. These results demonstrate the suitability of chitosan-based carbons for application in energy storage systems.

High-transparency and low-resistivity poly (methylmethacrylate) films containing silver nanowires and graphene-oxide nanoplatelets

Nanocomposite films containing silver nanowires (Ag NWs) and graphene-oxide nanoplatelets (GONPs) were formed on glass, and the nanocomposite films were then transferred to poly(methylmethacrylate) (PMMA) films. Scanning electron microscopy images showed that Ag NWs with a length of 20μm and a width of 80nm, together with GONPs with a size of 15μm, had been formed on the PMMA film and that the Ag NWs on the PMMA film were partially covered with the GONPs. While the transmittance of the PMMA film with the Ag NWs and the GONPs was almost the same as that of the PMMA film with the Ag NWs alone, the corresponding sheet resistance was decreased due to the generation of quaternary nitrogen in the GONPs, which the results of X-ray photoelectron spectroscopy and Raman spectroscopy confirmed. The transmittance and the sheet resistance of the PMMA film containing Ag NWs and GONPs were approximately 90% at 550nm and 24Ohm/sq, respectively.

Pt supported nitrogen doped hollow carbon spheres for the catalysed reduction of cinnamaldehyde

Carbon and nitrogen coated Stöber silica spheres were prepared by a standard procedure using acetonitrile at different CVD temperatures (800–1000°C) and as a function of time (1–4h). HF treatment was used to remove the silica from the carbon coated silica to give monodispersed nitrogen doped hollow carbon spheres (N-HCSs; shell thickness=50nm). The surface areas of the N-CSs increased significantly after removal of the SiO2 core (N-HCS=47m2/g). Platinum nanoparticles, prepared by a [Pt(COD)Cl2] deposition method were dispersed (d=2.8±0.4nm) on the N-HCS supports. Thermal treatment of the Pt/N-HCS900-4 (prepared at 900°C for 4h) in a 5% H2/Ar atmosphere at 120°C (Pt/N-HCS900-4-120) and 300°C (Pt/N-HCS900-4-300) gave metallic Pt (2.48%) which was confirmed by XRD and XPS studies. The XPS N1s spectra of Pt/N-HCS900-4-120 showed the presence of quaternary, pyridinic and pyrollic nitrogen atoms. These nitrogen doped carbon supported Pt nanoparticle catalysts were observed to reduce cinnamaldehyde to the unsaturated alcohol, cinnamyl alcohol (isopropanol/30bar H2/80°C) with >99% conversion and selectivity. The catalyst used in the reduction of cinnamaldehyde to cinnamyl alcohol could be recycled 12 times with minimal loss in conversion and this correlated with the small amount of Pt leaching or physical loss of catalyst (<2%). The corresponding Pt/catalyst made on undoped HCSs showed a much greater loss of activity with recycling. It is seen that N doping of carbon is an effective method to bind Pt to carbon.

Iron–nitrogen–activated carbon as cathode catalyst to improve the power generation of single-chamber air-cathode microbial fuel cells

In order to improve the performance of microbial fuel cell (MFC), iron–nitrogen–activated carbon (Fe–N–C) as an excellent oxygen reduction reaction (ORR) catalyst was prepared here using commercial activated carbon (AC) as matrix and employed in single chamber MFC. In MFC, the maximum power density increased to 2437±55mWm−2, which was 2 times of that with AC. The open circuit potential (OCP) of Fe–N–C cathode (0.47) was much higher than that of AC cathode (0.21V). The R0 of Fe–N–C decreased by 47% from 14.36Ω (AC) to 7.6Ω (Fe–N–C). From X-ray photoelectron spectroscopy (XPS), pyridinic nitrogen, quaternary nitrogen and iron species were present, which played an important role in the ORR performance of Fe–N–C. These results demonstrated that the as-prepared Fe–N–C material provided a potential alternative to Pt in AC air cathode MFC for relatively desirable energy generation and wastewater treatment.

Metal-free Nanoporous Carbon as a Catalyst for Electrochemical Reduction of CO2 to CO and CH4.

S-doped and dual S,N-doped polymer-derived carbons were studied as electrocatalysts for the reduction of CO2. Higher Faradaic efficiencies for conversion to CO and CH4 were obtained for S,N-doped carbon than its S-doped counterpart. The former showed a maximum Faradaic efficiency of 11.3% for CO and 0.18% for CH4 formation. The S,N-nanoporous carbon was better at decreasing the overpotential of the reduction process. The pyridinic nitrogen groups were found to be actively participating in binding CO2. The quaternary nitrogen and thiophenic groups were also involved in the reduction process. It is proposed that the positively charged sites on the carbon atoms, adjacent to pyridinic nitrogen, stabilize the CO2(.-) and COOH* intermediates, promoting the formation of CO. The surface basicity of the catalysts improved the CO2 reduction selectivity when competing with H2 evolution. N2 adsorption measurements suggested that ultra-micropores enhance the reduction of CO2 to CH4.

One-step synthesis of dual-transition metal substitution on ionic liquid based N-doped mesoporous carbon for oxygen reduction reaction

Nitrogen (N)-doped ordered mesoporous carbons (OMCs) with a dual transition metal system were synthesized as non-Pt catalysts for the ORR. The highly nitrogen doped OMCs were prepared by the precursor of ionic liquid (3-methyl-1-butylpyridine dicyanamide) for N/C species and a mesoporous silica template for the physical structure. Mostly, N-doped carbons are promoted by a single transition metal to improve catalytic activity for ORR in PEMFCs. In this study, our N-doped mesoporous carbons were promoted by the dual transition metals of iron and cobalt (Fe, Co), which were incorporated into the N-doped carbons lattice by subsequently heat treatments. All the prepared carbons were characterized by via transmission electron microscopy (TEM), X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS). To evaluate the activities of synthesized doped carbons, linear sweep was recorded in an acidic solution to compare the ORR catalytic activities values for the use in the PEMFC system. The dual transition metal promotion improved the ORR activity compared with the single transition metal promotion, due to the increase in the quaternary nitrogen species from the structural change by the dual metals. The effect of different ratio of the dual metals into the N doped carbon were examined to evaluate the activities of the oxygen reduction reaction.

Synthesis, antimicrobial evaluation and molecular modeling of 5-hydroxyisoquinolinium salt series; the effect of the hydroxyl moiety

In the present paper, we describe the synthesis of a new group of 5-hydroxyisoquinolinium salts with different lengths of alkyl side-chain (C10–C18), and their chromatographic analysis and biological assay for in vitro activity against bacterial and fungal strains. We compare the lipophilicity and efficacy of hydroxylated isoquinolinium salts with the previously published (non-hydroxylated) isoquinolinium salts from the point of view of antibacterial and antifungal versatility and cytotoxic safety. Compound 11 (C18) had to be excluded from the testing due to its low solubility. Compounds 9 and 10 (C14, C16) showed only moderate efficacy against G+ bacteria, notably with excellent potency against Staphyloccocus aureus, but no effect against G− bacteria. In contrast, non-hydroxylated isoquinolinium salts showed excellent antimicrobial efficacy within the whole series, particularly 14 (C14) against G+ strains and 15 (C16) against fungi. The electronic properties and desolvation energies of 5-hydroxyisoquinolinium and isoquinolinium salts were studied by quantum-chemistry calculations employing B3LYP/6-311++G(d,p) method and an implicit water-solvent simulation model (SCRF). Despite the positive mesomeric effect of the hydroxyl moiety reducing the electron density of the quaternary nitrogen, it is probably the higher lipophilicity and lower desolvation energy of isoquinolinium salts, which is responsible for enhanced antimicrobial versatility and efficacy.

Adsorptive Removal of Nitrate from Aqueous Solution Using Nitrogen Doped Activated Carbon.

Activated carbon (AC) has been widely applied for adsorptive removal of organic contaminants from aqueous phase, but not for ionic pollutants. In this study, nitrogen doped AC was prepared to increase the adsorption capacity of nitrate from water. AC was oxidized with (NH4)2S2O8 solution to maximize oxygen content for the first step, and then NH3 gas treatment was carried out at 950°C to aim at forming quaternary nitrogen (N-Q) species on AC surface (Ox-9.5AG). Influence of solution pH was examined so as to elucidate the relationship between surface charge and adsorption amounts of nitrate. The results showed that Ox-9.5AG exhibited about twice higher adsorption capacity than non-treatment AC at any initial nitrate concentration and any equilibrium solution pH (pHe) investigated. The more decrease in pHe value, the more adsorption amount of negatively charged nitrate ion, because the surface charge of AC and Ox-9.5AG could become more positive in acidic solution. The oxidation and consecutive ammonia treatments lead to increase in nitrogen content from 0.35 to 6.4% and decrease in the pH of the point of zero charge (pHpzc) from 7.1 to 4.0 implying that positively charged N-Q of a Lewis acid was created on the surface of Ox-9.5AG. Based on a Langmuir data analysis, maximum adsorption capacity attained 0.5-0.6 mmol/g of nitrate and adsorption affinity was 3.5-4.0 L/mmol at pHe 2.5 for Ox-9.5AG.

Facile synthesis of N-rich carbon quantum dots by spontaneous polymerization and incision of solvents as efficient bioimaging probes and advanced electrocatalysts for oxygen reduction reaction.

In this study, uniform nitrogen-doped carbon quantum dots (N-CDs) were synthesized through a one-step solvothermal process of cyclic and nitrogen-rich solvents, such as N-methyl-2-pyrrolidone (NMP) and dimethyl-imidazolidinone (DMEU), under mild conditions. The products exhibited strong light blue fluorescence, good cell permeability and low cytotoxicity. Moreover, after a facile post-thermal treatment, it developed a lotus seedpod surface-like structure of seed-like N-CDs decorating on the surface of carbon layers with a high proportion of quaternary nitrogen moieties that exhibited excellent electrocatalytic activity and long-term durability towards the oxygen reduction reaction (ORR). The peak potential was -160 mV, which was comparable to or even lower than commercial Pt/C catalysts. Therefore, this study provides an alternative facile approach to the synthesis of versatile carbon quantum dots (CDs) with widespread commercial application prospects, not only as bioimaging probes but also as promising electrocatalysts for the metal-free ORR.

Stable non-covalent labeling of layered silicate nanoparticles for biological imaging

Layered silicate nanoparticles (LSN) are widely used in industrial applications and consumer products. They also have potential benefits in biomedical applications such as implantable devices and for drug delivery. To study how nanomaterials interact with cells and tissues, techniques to track and quantify their movement through different biological compartments are essential. While radiolabels can be very sensitive, particularly for in vivo studies, fluorescent labeling has been preferred in recent years because of the array of methods available to image and quantify fluorescent nanoparticles. However, labeling can be problematic, especially if it alters the physical properties of the nanomaterial. Herein is described a novel non-covalent labeling technique for LSN using readily available fluorescent dimeric cyanine dyes without the need to use excess amounts of dye to achieve labeling, or the need for removal of unbound dye. The approach utilizes the cationic binding properties of layered silicate clays and the multiple quaternary nitrogens associated with the dyes. Preparation of YOYO-1 labeled LSN with optimal dispersion in aqueous media is presented. The utilization of the labeled particles is then demonstrated in cell binding and uptake studies using flow cytometry and confocal microscopy. The labeled LSN are highly fluorescent, stable and exhibit identical physical properties with respect to the unlabeled nanoparticles. The general approach described here is applicable to other cyanine dyes and may be utilized more widely for labeling nanoparticles that comprise a crystalline plate structure with a high binding capacity.

Novel trans-disubstituted hexaaza-macrocyclic ligands containing pyridine head units: Synthesis, disubstitution and colorimetric properties

A trans-N,N′-methylated hexaazamacrocycle precursor L3, derived from the hexadentate polyamine macrocycle L (Py2[18]aneN6), was synthesized for the first time. The crystal structures of the intermediates L1·8H2O and L2I2·H2O showing two trans quaternary nitrogen atoms have also been determined by single-crystal X-ray crystallography.By the alkylation of the trans secondary amines present in L3, two novel macrocyclic molecular probes 1 and 2 linked to two nitrophenylurea and two nitrophenylthiourea groups, respectively, are reported. Crystals of 1·2CDCl3 suitable for single-crystal X-ray diffraction analysis were also obtained.The coordination ability of compounds 1 and 2 toward hydrated nitrate salts of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) was studied. Their responses toward different anions (fluoride (F−), chloride (Cl−), bromide (Br−), iodide (I−), hydroxide (OH−), acetate (AcO−), cyanide (CN−), dihydrogen phosphate (H2PO4−), nitrate (NO3−) and perchlorate (ClO4−)) in DMSO solution were evaluated by UV–vis absorption spectroscopy.The immobilization of probe 1 in cellulose supported systems to evaluate its efficiency in the fast recognition of different anions (F−, AcO−, CN−, H2PO4−) in aqueous phase was also described.