Diaminomaleonitrile Research Articles

Photochemical and electrochemical behavior of a molecular probe: Fluorescence on-off-on response to detect multiple ions (Cu2+, ClO− and CN−) with different rate of reaction

A molecular probe 3 containing phenyl substituted imidazolyl unit and diaminomaleonitrile (DAMN) moiety has been synthesized and characterized. Photophysical and electrochemical behavior probe 3 were studied in partial aqueous medium (ACN/H2O, 9.5:0.5 v/v). Probe 3 upon interaction with different class of ions showed sensitivity for Cu2+, ClO− and CN− ions with different response time and reaction rates due to variation in intramolecular charge transfer (ICT) process. Both Cu2+ and ClO− ions displayed enhanced emission due to hydrolysis of imine bond to form compound 2 in the medium whereas, with CN− fluorescence quenching was observed due to the deprotonation of –OH/–NH2 functions. The kinetic and optical behavior of the probe suggested that interaction occurred in two steps with Cu2+ (complexation and hydrolysis; absk1,2,3(Cu2+) = 1.17, 0.74 and 0.06 s−1) and ClO− (hydrolysis and deprotonation; absk1,2(ClO−) = 3.0 and 0.60 s−1) ions while CN− (absk1,2(CN−) = 2.13 and 1.66 s−1) induces deprotonation in one step. The interaction of probe 3 with ClO− was relatively fast than with Cu2+/CN− ions. Job's plot analysis between probe 3 and ions revealed a 1:1 (Cu2+/ClO−) and 1:2 (CN−) ratio stoichiometry with good limit of detection (nM) and binding affinity (LOD, 17; KCu2+ = 3.23 × 106 M−1; LOD, 18.5; KClO− = 5.23 × 105 M−1 and LOD, 23.2; KCN− = 5.50 × 109 M−2) respectively. Probe 3 displayed a naked–eye sensitive fluorescence response to detect tested ions on test paper strips and good recovery percentage of ions in real water sample analysis.

Solvothermal Polymerization of Diaminomaleonitrile Reveals Optimal Green Solvents for the Production of C=N-Based Polymers.

Solvothermal polymerization (STP) of diaminomaleonitrile (DAMN) was evaluated using a wide variety of solvents and in the temperature range from 80 to 170 °C. The highest yields, almost quantitative, were achieved with protic n-alcohols such as n-pentanol or n-hexanol at 130 and 150 °C, respectively. The kinetic behavior was studied by gravimetry and the DAMN consumption was monitored by UV-vis spectroscopy and HPLC. GC-MS identified byproducts of the DAMN hydrolysis and oxidation reactions, which were significantly reduced when n-pentanol or n-hexanol were used with respect to hydrothermal conditions. This led to an exploration of compositional changes and microstructural variations by FTIR and NMR spectroscopy and simultaneous thermal analysis. n-Hexanol appears to be an ideal eco-friendly solvent for the DAMN self-STP. The results presented here are not only of interest for the design of polymeric materials based on C=N structures but also show remarkable implications for prebiotic chemistry.

Investigation Of The Schottky Diode Performance of a new Diaminomaleonitrile‐Based Organic Material with D‐Π‐A Architecture

AbstractIn this paper, firstly, a new organic material 9 containing triphenylamine (TPA) unit as an electron donor and diaminomaleonitrile (DAMN) unit as an electron acceptor and thiophene scaffold as a π‐linker bridge was designed for diode applications according to D‐π‐A architecture. The organic material 9 was synthesized in four reaction steps with excellent yield (94 %), and fully characterized by 1H NMR, 13C NMR, FTIR, and HRMS spectra. The diode performance properties of the obtained organic material were examined in detail. Current‐voltage (I–V) and capacitance‐voltage (C–V) measurements of this diode were carried out. As a result of the analysis of these measurements, the effect of the organic material used as the interface material on the electrical properties of the diode was analyzed.

Functionalized metal organic framework (MIL-101(Cr)) as selective adsorbent for the mitigation of uranium (VI) from contaminated lake water

Metal-organic frameworks (MOFs) received much attention due to their distinct porous structure. Diaminomaleonitrile (DAMN) functionalized chromium (III) terephthalate MOF (MIL-101(Cr)) was developed using a facile method as a promising adsorbent for U removal. The functionalized adsorbent contained abundant amine and cyanide groups onto the coordinatively unsaturated metal binding sites. The DAMN-functionalized MIL-101(Cr) was thoroughly characterized. The adsorbent exhibited maximum Langmuir adsorption capacity of 743 mg/g for U at pH 6 and room temperature. Different coexisting ions, having concentration within 10–50 mg/L, show negligible influence on the U adsorption (86.0–99.3 % removal). The effects of other ions on the U removal were studied in terms of U ionic speciation in the aqueous solution. The surface-grafted −C≡N and –NH2 groups were responsible for the coordinative interactions with the U(VI) ionic moieties. The MIL-101(Cr)_DAMN adsorbent was also subjected to five consecutive adsorption–desorption cycles, with >90.5 % U removal after the 5th cycle. An adsorption-pore diffusion based transport model was used to analyze the adsorption kinetics and estimation of the pore diffusivity. The effectiveness of the developed adsorbent was also demonstrated by a batch kinetic run using U contaminated lake water. In general, this research demonstrates the straightforward design and development of DAMN-functionalized MIL-101(Cr) as an effective adsorbent for the selective uptake of U(VI) from aqueous medium.

Diaminomaleonitrile as a high-throughput precursor for alternative layered C=N-based conjugated polymers to carbon nitrides

In the present work, the fast production of C=N-based conjugated macrostructures from the bulk thermal polymerization of diaminomaleonitrile (DAMN) is discussed. These high-throughput syntheses showed air tolerance and were studied under different temperature regimes, from 160 to 200 °C, according to solid-state or melt polymerization (MP). This study displays not only the effect of temperature and exposure to air but also the gases evolved during the polymerization reactions. These volatiles were suitably analysed, providing relevant information about the elimination processes that take place during the course of these thermolytic reactions. The microstructure and physical properties of these black polymer materials obtained were determined by elemental analysis, Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and ultraviolet–visible (UV–Vis) spectroscopies, X-ray diffraction (XRD), thermogravimetry (TG), electron paramagnetic resonance (EPR), electrochemistry measurements and scanning electron microscopy (SEM). The interpretation of all these data suggests that a two-dimensional (2-D) macrostructure based on N-heterocycles as diazines is predominant, regardless of the state of monomer aggregation during the course of the polycondensations. Interestingly, these 2-D polymeric systems present characteristic analogues with well-documented carbon nitrides (g-C3N4), with similar magnetic, electrochemical, optical and catalytic properties. Thus, DAMN polymers are proposed as alternative materials to relevant g-C3N4, as their synthetic process is easy, quick and highly efficient.

Impact of M Dwarfs Ultraviolet Radiation on Prebiotic Chemistry: The Case of Adenine.

To date, several exoplanets have been found to orbit within the habitable zone of main sequence M stars (M dwarfs). These stars exhibit different levels of chromospheric activity that produces ultraviolet (UV) radiation. UV may be harmful to life, but it can also trigger reactions of prebiotic importance on the surface of a potentially habitable planet (PHP). We created a code to obtain the adenine yield for a known adenine synthesis route from diaminomaleonitrile (DAMN). We used computational methods to calculate the reaction coefficient rates (photolysis rate J and rate constant K) for the intermediate molecules DAMN, diaminofumaronitrile (DAFN), and 4-aminoimidazole-5-carbonitrile (AICN) of the adenine synthesis route. We used stellar UV sources and a mercury lamp to compare the theoretical results with experiments performed with lamps. The surface UV flux of planets in the habitable zone of two active M dwarfs (Proxima Centauri and AD Leonis) and the prebiotic Earth was calculated using the photochemical model ATMOS, considering a CO2-N2-H2O atmosphere. We obtained UV absorption coefficients for DAMN and DAFN and thermodynamic parameters that are useful for prebiotic chemistry studies. According to our results, experiments using UV lamps may underestimate the photolysis production of molecules of prebiotic importance. Our results indicate that photolysis reactions are fast with a yield of 50% of AICN in 10 s for the young Sun and ∼1 h for Proxima Centauri b. Planets around active M dwarfs may provide the most favorable environment for UV-mediated production of compounds relevant to the origins of life. The kinetic reaction AICN + HCN  adenine is the bottleneck of the pathway with reaction rates <10-22 L/(mol·s).

Air effect on both polymerization kinetics and thermal degradation properties of novel HCN polymers based on diaminomaleonitrile

The impact of air on the bulk polymerization kinetics of diaminomaleonitrile (DAMN), tetramer of HCN, and thermal degradation properties of this resulting conjugated C=N polymeric system is investigated under different temperature regimes and environments. This study shows the effect of exposure to air and oxygen, time, temperature, and evolved gases during DAMN polymerization reactions, which can be suitably monitored by differential scanning calorimetry (DSC) through both dynamic and isothermal measurements. Thus, low heating rates and isothermal scans at 150-170 °C allow us to describe the solid-state polymerization (SSP) of DAMN, and those experiments at 190, 195 and 200 °C and higher heating runs define its melt polymerization (MP) behaviour. Both processes are highly efficient, possibly due to the self-acceleration nature of their kinetics, which is consistent with a three-step Šesták-Berggren (SB) model. The oxygen effect was analysed to determine their tolerance to this variable and confirm the nonradical nature of the mechanism under study. In addition, a detailed thermal characterization by simultaneous DSC/thermogravimetry coupled to mass spectrometry (TG-MS) of these singular polymeric systems obtained under air atmosphere has been completed, and the improvement of the thermal stability of those samples prepared by an SSP at lower temperature was confirmed. The present work offers lower-cost and simpler synthetic methods to obtain this novel class of promising multifunctional polymeric materials through highly efficient and very fast processes.

Computational study of toxic gas removal

Cages and porous polymers pitch a distinctive prospect to sequester/adsorption for CO2 and other toxic gasses, nevertheless the ideal structural proposal has always been difficult to engineer. Herein, we have computationally proposed a small cage index that uses diaminomaleonitrile (DAMN) to connect two p-cresol units that bind in a cage to adsorb toxic gas molecules and their transformation to trap them. Quantum mechanical calculations using density functional theory (DFT) show that the hydroxyl group (OH) of the p-cresol and the DAMN nitrile groups enable future binding for toxic gasses. Hydrogen bonds were observed between the two terminal oxygen atoms (O) of CO2 and hydrogens of ammonia (NH3) with the inner hydroxyl group of the proposed cage. Based on the simulated potential energy of binding of toxic gasses to the cage, we hypothesized that all toxic gasses are readily accessible to the cage. These results explain that the cage based on DAMN has an excessive potency for challenging NH3, Cl2 capture, and CO2 conversion.

From ACQ to AIE: The CN(π)-(π)Ar interaction driven structural and photophysical properties of aromatic ring conjugated novel diaminomaleonitrile derivatives

Studying solid and solution state photoluminescence properties are exclusive to understanding Aggregation Caused Quenching (ACQ) and Aggregation Induced Emission (AIE) behaviour of organic molecules to explore the mechanism of molecular luminescence in greater detail. A unique hydrogen-bonded dimer with imperative interaction (CN)π---π(Ar) was designed and synthesized by selecting diaminomaleonitrile (DMN) as stator and decorated with different aromatic rotors (phenyl to pyrene). Depending on the intermolecular interaction present in the molecular system, (AIE) or (ACQ) has been observed and found to be tunable. The single-crystal x-ray diffraction analysis of these derivatives shows that AIE characteristics could be seen where to (CN)π---π(Ar) intermolecular interactions between the aromatic rotors and stator, coupled with NH–-–NC intermolecular hydrogen bonding is present, while the absence of these interaction reflected in ACQ observation. The significant impacts of steric, conjugation and electronic effects on the ACQ / AIE properties are presented based on crystallography analysis, optical spectra measurements and theoretical calculations.

Processable amidoxime functionalized porous hyper-crosslinked polymer with highly efficient regeneration for uranium extraction

Uranium is not only toxic and radioactive, even more an important resource to ensure the nuclear energy development. This work reported an amidoxime-based hyper-crosslinked polymeric resin adsorbent (HWB-AO) to extract uranium from ocean. The monolithic matrix was prepared by suspension polymerization using styrene (St) and divinylbenzene (DVB), followed by post-polymerization modification to graft diaminomaleonitrile (DAMN) and conduct amidoximation to introduce amidoxime groups (AO) in its interior and surface. AO can enhance the affinity to uranium and hydrophilicity to accelerate the uranium adsorption. The monolithic structure overcome the problem that powder adsorbent is easy to drain in real seawater, so the monolithic is easier to apply. The batch adsorption experiments results showed that HWB-AO has an magnificent uranium removal rate (85%) and the maximum adsorption capacity (qe,max) is 256.4 mg g−1. In addition, HWB-AO still maintains a giant adsorption efficiency after eight times adsorption–desorption cycles and is environmentally friendly. Concurrently, HWB-AO exhibits excellent selectivity and removal rate (greater than88%) in modified seawater. Therefore, HWB-AO is considered as a potential adsorbent to perform uranium extraction from natural seawater.

An antibacterial and antifouling amidoxime-functionalized graphene oxide aerogel for selective uranium adsorption in Salt Lake water

Uranium plays an important role in nuclear energy and the abundant amount of uranium could be explored in Salt Lake water. However, the existence of pollutants, microorganisms and coexisting ions make it very challenging to selectively adsorb uranium from Salt Lake. Herein, a graphene oxide-based aerogel (CS-GO-DO/ZnO) adsorbent was prepared by compounding graphene oxide (GO) with amidoximated diaminomaleonitrile (DO), ZnO particles and Chitosan (CS) to selectively adsorb uranium. Batch adsorption experiments revealed that the CS-GO-DO/ZnO aerogel showed high adsorption capacity and good selectivity for uranium and the maximum adsorption capacity can reach 561.09 mg/g in pure uranium solution. Most importantly, the synthesized CS-GO-DO/ZnO aerogel showed excellent antibacterial and antifouling performance, and the adsorption capacity can still reach more than 96 % of the pure solution even in the presence of abundant bacteria and pollutants. Finally, the synthesized material was applied in natural Salt Lake water and it presented superior uranium adsorption capacity (3.67 mg/g). Therefore, the CS-GO-DO/ZnO aerogel can be potentially used as a promising adsorbent for uranium extraction.

A BODIPY‐Diaminomaleonitrile Based Water‐Soluble Fluorescent Probe for Selective “Off‐On” Detection of Hypochlorite**

AbstractA fluorescent probe (BODIPY‐DAMN) with high selectivity and sensitivity for the detection of hypochlorite (ClO−) was designed and synthesized. The probe uses boron‐dipyrromethene (BODIPY) as fluorophore, carboxyl group modification to improve its water solubility, and diaminomaleonitrile (DAMN) as recognition group to recognize ClO−. BODIPY‐DAMN exhibits an “off‐on” fluorescence response towards ClO−. In the range of 10.0 to 250.0 μM, there is a good linear relationship between the emission intensity and HClO concentration, and the detection limit is 298 nM. Hypochlorite in actual water samples was determined with recovery of 89.5 % and 112.0 %. In addition, BODIPY‐DAMN has low cytotoxicity, and has been used to determine endogenous ClO− in mouse melanoma cells (B16‐F10), human neuroblastoma cells (SH‐SY5Y) and zebrafish. The results of this study provide a new strategy for further research on the physiological and pathological effects of hypochlorite.

Synthesis of a porous amidoxime modified hypercrosslinked benzil polymer and efficient uranium extraction from water

Benzil was hypercrosslinked to produce a novel hypercrosslinked porous organic polymer skeleton (HCP-CO) with an ultrahigh Brunauer-Emmett-Teller (BET) surface area of 605.4 m2·g−1. The skeleton was grafted with diaminomaleonitrile (DAMN) via a simple Schiff base reaction, and then reacted with hydroxylamine hydrochloride (NH2OH·HCl) to produce an amidoxime-modified hypercrosslinked benzil polymer (HCP-AO) possessing many amidoxime groups. The chelation of the amidoxime group and uranium (VI) and porous structure provided HCP-AO with excellent adsorption performance. The maximum adsorption capacity for the uranium of HCP-AO can reach 370.9 mg·g−1 at pH = 6. Moreover, the adsorption process agreed well with the Langmuir and pseudo-second-order models, thus indicating it was monolayer chemical adsorption. HCP-AO demonstrated excellent selectivity and recyclability; furthermore, the removal rate for uranium still remained at 66.35% in the coexistence of metal ions in simulated seawater. Furthermore, after five adsorption–desorption cycles, the adsorption capacity of HCP-AO slightly reduced. To summarize, we synthesized an efficient adsorbent that possesses high adsorption capacity, selectivity, and recyclability; it has good potential for uranium extraction from water.

HCN-derived polymers from thermally induced polymerization of diaminomaleonitrile: A non-enzymatic peroxide sensor based on prebiotic chemistry

HCN-derived polymers have recently attracted considerable attention due to their promising applications as multifunctional materials. This study, inspired by plausible early Earth geochemical conditions, describes a strategy to synthesize them from the self-initiated thermal bulk polymerization of the HCN tetramer, diaminomaleonitrile (DAMN), with outstanding sensing properties. These conjugated polymers were obtained through noncatalysed and simple isothermal reactions at 170 °C in the solid-state, and experiments at 190 °C permitted polymerization in the melt. Both processes are highly efficient, allowing quantitative yields of the end products. The conductivity properties of both polymers have been explored to show their high potential, especially DAMN polymers synthesized in melt, as nonenzymatic peroxide sensors. To better understand the differences found between the two series, structural characterisation was carried out using compositional data, Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and X-ray photoelectron (XPS) spectroscopies, and X-ray diffraction (XRD) measurements. The interpretation of the structural data suggests that a two-dimensional (2-D) macrostructure based on N-heterocyclics is predominant regardless of the state of monomer aggregation during the course of polymerization, but preferably formed in the melt. The morphological and thermal stability properties of the polymers based on DAMN were also evaluated. Finally, the most likely mechanisms based on the dehydrocyanation and deamination reactions that take place during the polymerization reaction are proposed. This study demonstrates the robust and straightforward character of these thermally activated polymerizations, which are of interest to chemical evolution research and to current materials and surface science.

Programmed Formation of HCN Oligomers through Organosulfur Catalysis.

An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN, 1) is described starting from readily available acetone cyanohydrin as the source of hydrogen cyanide (HCN). Diaminomaleonitrile (DAMN) is known to be an important intermediate in heterocyclic and medicinal chemistry as well as being a possible precursor for the origin of life's hypothesis within prebiotic chemistry. The mechanism of its formation through organosulfur catalysis has been investigated by electrospray ionization mass spectrometry (ESI-MS) using two newly synthesized cationic "marker" molecules as a tool that allows for sensitive detection. As a result, the proposed mechanism of a thiocyanate-mediated synthesis of the HCN tetramer DAMN starting from organic disulfides was confirmed.

A Comprehensive Review of HCN-Derived Polymers

HCN-derived polymers are a heterogeneous group of complex substances synthesized from pure HCN; from its salts; from its oligomers, specifically its trimer and tetramer, amino-nalono-nitrile (AMN) and diamino-maleo-nitrile (DAMN), respectively; or from its hydrolysis products, such as formamide, under a wide range of experimental conditions. The characteristics and properties of HCN-derived polymers depend directly on the synthetic conditions used for their production and, by extension, their potential applications. These puzzling systems have been known mainly in the fields of prebiotic chemistry and in studies on the origins of life and astrobiology since the first prebiotic production of adenine by Oró in the early years of the 1960s. However, the first reference regarding their possible role in prebiotic chemistry was mentioned in the 19th century by Pflüger. Currently, HCN-derived polymers are considered keys in the formation of the first and primeval protometabolic and informational systems, and they may be among the most readily formed organic macromolecules in the solar system. In addition, HCN-derived polymers have attracted a growing interest in materials science due to their potential biomedical applications as coatings and adhesives; they have also been proposed as valuable models for multifunctional materials with emergent properties such as semi-conductivity, ferroelectricity, catalysis and photocatalysis, and heterogeneous organo-synthesis. However, the real structures and the formation pathways of these fascinating substances have not yet been fully elucidated; several models based on either computational approaches or spectroscopic and analytical techniques have endeavored to shed light on their complete nature. In this review, a comprehensive perspective of HCN-derived polymers is presented, taking into account all the aspects indicated above.

Solid-state polymerization of diaminomaleonitrile: Toward a new generation of conjugated functional materials

The solid-state polymerization (SSP) of organic molecules to form two-dimensional (2D) materials remains a challenge, especially when these reactions are performed in one pot using a single reagent. As will be shown, the SSP of the HCN tetramer diaminomaleonitrile (DAMN) may be an excellent example of these reactions. Dynamic experiments by differential scanning calorimetry (DSC) allow the analysis of the thermally initiated bulk polymerization of DAMN. Under nonisothermal measurements at low heating rates, a multiple-step polymerization reaction takes place. The SSP of DAMN is highly efficient, possibly due to the autocatalytic nature of its kinetics, which are consistent with the two-parameter Šesták-Berggren (SB) model and describe the three stages found in its complicated mechanism, confirmed also from an analysis of the variation in the apparent activation energy with the conversion degree. Relevant mechanistic aspects, such as the dehydrocyanation and deamination processes during SSP, are extracted by thermogravimetry-mass spectrometry (TG-MS). Moreover, some structural and morphological properties of these materials are characterized by Fourier-transform infrared (FTIR) spectroscopy and microscopy. All this information allows us to propose hypothetical pathways for the production of a complex conjugated system, predominantly constituted by a 2D macrostructure based on imidazole rings. This work opens up new possibilities for the synthesis of functional poly(heterocycle) systems, expanding our view of a plausible prebiotic chemical reaction space and providing the foundation for systematic studies of the structure-property relationships of novel HCN-derived polymers, which are currently of great interest in the fields of materials and surface science.

Highly efficient melt polymerization of diaminomaleonitrile

HCN polymers are of great interest in research on the origin of life and, currently, in materials science because they have shown potential for the design of electrical devices, (photo)catalysts and biomedicine. Herein, calorimetric measurements have successfully described the bulk polymerization of HCN tetramer, diaminomaleonitrile (DAMN). Two series of nonisothermal experiments were carried out by differential scanning calorimetry (DSC), and low-heating rate (β) the thermograms (β ≤ 5 °C/min) indicated that the polymerization is initiated at temperatures lower than the DAMN melting point, ~180 °C; while higher heating rates results in a rapid polymerization reaction, which occurs entirely in the liquid phase. The DSC data were analysed using model-free linear iso-conversional methods to estimate kinetic parameters, such as activation energy, and a suitable kinetic model was proposed for these thermal polymerizations in the melt. A preliminary structural and morphological characterization by means of Fourier transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM) was also completed. This study demonstrated the autocatalytic, highly efficient and straightforward character of this stimulated thermal polymerization of DAMN and, to the best of our knowledge, describes for the first time a systematic and extended kinetic analysis to gain mechanistic insights into this process. The latter was done through the help of simultaneous thermogravimetry (TG)-DSC and in situ mass spectrometry (MS) technique to investigate the gas products generated during these melt polymerizations. These analyses revealed that deamination and dehydrocyanation processes are two relevant reactions involved in DAMN polymerization mechanism.

Monitoring the Reactivity of Formamide on Amorphous SiO2 by In-Situ UV-Raman Spectroscopy and DFT Modeling.

Formamide has been recognized in the literature as a key species in the formation of the complex molecules of life, such as nucleobases. Furthermore, several studies reported the impact of mineral phases as catalysts for its decomposition/polymerization processes, increasing the conversion and also favoring the formation of specific products. Despite the progresses in the field, in situ studies on these mineral-catalyzed processes are missing. In this work, we present an in situ UV-Raman characterization of the chemical evolution of formamide over amorphous SiO2 samples, selected as a prototype of silicate minerals. The experiments were carried out after reaction of formamide at 160 °C on amorphous SiO2 (Aerosil OX50) either pristine or pre-calcined at 450 °C, to remove a large fraction of surface silanol groups. Our measurements, interpreted on the basis of density functional B3LYP-D3 calculations, allow to assign the spectra bands in terms of specific complex organic molecules, namely, diaminomaleonitrile (DAMN), 5-aminoimidazole (AI), and purine, showing the role of the mineral surface on the formation of relevant prebiotic molecules.

Efficient adsorbent for recovering uranium from seawater prepared by grafting amidoxime groups on chloromethylated MIL-101(Cr) via diaminomaleonitrile intermediate

Here, reaction of a chloromethylated metal-organic framework (MOF) MIL-101 with diaminomaleonitrile (DAMN) following with an amidoximation reaction successfully produced a novel amidoxime functionalized porous material (MIL-101-AO). The chelation of amidoxime group to uranium and the large specific surface area afforded MIL-101-AO excellent selective adsorption ability for U (VI) in aqueous solutions (586 mg·g−1). Furthermore, MIL-101-AO showed much stronger selective adsorption for U (VI) than other co-existing metallic ions in the artificial seawater (removal rate reached 96%). The influence factors on the adsorption process were evaluated by batch adsorption experiments under different condition. The process of adsorbing uranium on MIL-101-AO fitted with the Langmuir model and the pseudo-second-order kinetic model. The △H° and △G° values of uranium adsorption indicated that it was an endothermic heat process; a higher adsorption temperature could promote the adsorption on MIL-101-AO. All the experimental results indicated that MIL-101-AO was an adsorbent with the application value of extracting uranium in seawater.