Synthesis of Pillar[5]arene- and Phosphazene-Linked Porous Organic Polymers for Highly Efficient Adsorption of Uranium

It is crucial to design efficient adsorbents for uranium from natural seawater with wide adaptability, effectiveness, and environmental safety. Porous organic polymers (POPs) provide superb tunable porosity and stability among developed porous materials. In this work, two new POPs, i.e., HCCP-P5-1 and HCCP-P5-2 were rationally designed and constructed by linked with macrocyclic pillar[5]arene as the monomer and hexachlorophosphate as the core via a macrocycle-to-framework strategy. Both pillar[5]arene-containing POPs exhibited high uranium adsorption capacity compared with previously reported macrocycle-free counterparts. The isothermal adsorption curves and kinetic studies showed that the adsorption of POPs on uranium was consistent with the Langmuir model and the pseudo-second-order kinetic model. Especially, HCCP-P5-1 has reached 537.81 mg/g, which is greater than most POPs that have been reported. Meanwhile, the comparison between both HCCP-P5-1 and HCCP-P5-2 can illustrate that the adsorption capacity and stability could be adjusted by the monomer ratio. This work provides a new idea for the design and construction of uranium adsorbents from macrocycle-derived POPs.

[1]  Mingzhang Lin,et al.  Effects of chain conformation on uranium adsorption performance of amidoxime adsorbents , 2023, Separation and Purification Technology.

[2]  Bing Yang,et al.  Synthesis of an Acidochromic and Nitroaromatic Responsive Hydrazone-Linked Pillararene Framework by a Macrocycle-To-Framework Strategy. , 2022, Angewandte Chemie.

[3]  Meng Li,et al.  Construction of Hydrazone-Linked Macrocycle-Enriched Covalent Organic Frameworks for Highly Efficient Photocatalysis , 2022, Chemistry of Materials.

[4]  A. Sakr,et al.  Removal of uranium from nuclear effluent using regenerated bleaching earth steeped in β‒naphthol , 2022, Radiation Physics and Chemistry.

[5]  J. S. Al-Otaibi,et al.  Synthesis of a New Chelating Iminophosphorane Derivative (Phosphazene) for U(VI) Recovery , 2022, Polymers.

[6]  Menghan Li,et al.  Pillararene-based molecular-scale porous materials. , 2021, Chemical communications.

[7]  Yinghua Jin,et al.  A pillar[5]arene-based covalent organic framework with pre-encoded selective host–guest recognition , 2021, Chemical science.

[8]  Long Chen,et al.  Macrocycle-derived hierarchical porous organic polymers: synthesis and applications. , 2021, Chemical Society reviews.

[9]  Zhihui Wang,et al.  Highly efficient removal of uranium(VI) from aqueous solution using the Chitosan- Hexachlorocyclotriphosphazene composite , 2021, Journal of Radioanalytical and Nuclear Chemistry.

[10]  Xiyan Xu,et al.  Efficient electrosorption of uranyl ions by a homemade amidoxime‐modified carbon paper‐based electrode in acidic aqueous condition , 2021, Journal of Chemical Technology & Biotechnology.

[11]  Hongxing Dong,et al.  Synthesis of phosphorylated hyper-cross-linked polymers and their efficient uranium adsorption in water. , 2021, Journal of hazardous materials.

[12]  Q. Yan,et al.  Endowing 2,6-bis-triazolyl-pyridine of poor extraction with superior efficiency for actinide/lanthanide separation at high acidity by anchoring to a macrocyclic scaffold. , 2021, Journal of hazardous materials.

[13]  Shuang Liu,et al.  Graphene Oxide Membranes for Tunable Ion Sieving in Acidic Radioactive Waste , 2021, Advanced science.

[14]  Zhanhu Guo,et al.  In-situ synthesis of uranyl-imprinted nanocage for selective uranium recovery from seawater. , 2021, Angewandte Chemie.

[15]  Baowei Hu,et al.  Highly efficient U(VI) capture by amidoxime/carbon nitride composites: Evidence of EXAFS and modeling. , 2021, Chemosphere.

[16]  Xiaodong Wang,et al.  Active biochar support nano zero-valent iron for efficient removal of U(VI) from sewage water , 2021 .

[17]  G. Ning,et al.  Construction of rigid ionic porous organic polymers (iPOPs) via Zincke reaction with tunable absorption behaviors , 2021, Journal of Porous Materials.

[18]  G. Ning,et al.  A boranil-based conjugated microporous polymer for efficient visible-light-driven heterogeneous photocatalysis , 2021 .

[19]  G. Ning,et al.  β-Diketone boron difluoride dye-functionalized conjugated microporous polymers for efficient aerobic oxidative photocatalysis , 2021, Catalysis Science & Technology.

[20]  Baowei Hu,et al.  Aluminum-based metal-organic frameworks (CAU-1) highly efficient UO22+ and TcO4- ions immobilization from aqueous solution. , 2020, Journal of hazardous materials.

[21]  Xiaoqing Xie,et al.  Highly efficient removal of uranium(VI) from aqueous solution using poly(cyclotriphosphazene-co-polyethyleneimine) microspheres , 2020, Journal of Radioanalytical and Nuclear Chemistry.

[22]  G. Ning,et al.  Construction of Ionic Porous Organic Polymers (iPOPs) via Pyrylium Mediated Transformation , 2020, Chinese Journal of Polymer Science.

[23]  G. Ning,et al.  Guest induced morphology transitions of star shaped pillar[5]arene trimer via endo host-guest and “exo-wall” electron-transfer interactions , 2020 .

[24]  Juewen Liu,et al.  Regenerable and stable sp2 carbon-conjugated covalent organic frameworks for selective detection and extraction of uranium , 2020, Nature Communications.

[25]  G. Ning,et al.  Pillar[5]arene-Derived Microporous Polyaminal Networks with Enhanced Uptake Performance for CO2 and Iodine , 2020 .

[26]  Lixian Sun,et al.  High Sorption Capacity of U(VI) by COF-Based Material Doping Hydroxyapatite Microspheres: Kinetic, Equilibrium and Mechanism Investigation , 2019, Journal of Inorganic and Organometallic Polymers and Materials.

[27]  Zhanhu Guo,et al.  Ultrafast and highly selective uranium extraction from seawater by hydrogel-like spidroin-based protein fiber. , 2019, Angewandte Chemie.

[28]  J. Chen,et al.  Phosphonate-Decorated Covalent Organic Frameworks for Actinide Extraction: A Breakthrough Under Highly Acidic Conditions , 2019, CCS Chemistry.

[29]  Zhi Gao,et al.  Ammoniating Covalent Organic Framework (COF) for High‐Performance and Selective Extraction of Toxic and Radioactive Uranium Ions , 2019, Advanced science.

[30]  P. Gao,et al.  Highly fluorescent conjugated microporous polymers for concurrent adsorption and detection of uranium , 2019, Journal of Materials Chemistry A.

[31]  J. Chew,et al.  Introduction of amino groups into polyphosphazene framework supported on CNT and coated Fe3O4 nanoparticles for enhanced selective U(VI) adsorption , 2019, Applied Surface Science.

[32]  Shoujian Li,et al.  Synthesis of Microporous Covalent Phosphazene-Based Frameworks for Selective Separation of Uranium in Highly Acidic Media Based on Size-Matching Effect. , 2018, ACS applied materials & interfaces.

[33]  L. Wojtas,et al.  Covalent Organic Frameworks as a Decorating Platform for Utilization and Affinity Enhancement of Chelating Sites for Radionuclide Sequestration , 2018, Advanced materials.

[34]  Jun Wang,et al.  Hierarchically structured layered-double-hydroxides derived by ZIF-67 for uranium recovery from simulated seawater. , 2017, Journal of hazardous materials.

[35]  Jun Wang,et al.  Interfacial growth of a metal–organic framework (UiO-66) on functionalized graphene oxide (GO) as a suitable seawater adsorbent for extraction of uranium(VI) , 2017 .

[36]  Wenbin Lin,et al.  Functionalized Porous Aromatic Framework for Efficient Uranium Adsorption from Aqueous Solutions. , 2017, ACS applied materials & interfaces.

[37]  Shoujian Li,et al.  "Stereoscopic" 2D super-microporous phosphazene-based covalent organic framework: Design, synthesis and selective sorption towards uranium at high acidic condition. , 2016, Journal of hazardous materials.

[38]  M. G. Warner,et al.  Surface functionalized nanostructured ceramic sorbents for the effective collection and recovery of uranium from seawater. , 2016, Dalton transactions.

[39]  Ryan P. Lively,et al.  Seven chemical separations to change the world , 2016, Nature.

[40]  Shoujian Li,et al.  Modifiable diyne-based covalent organic framework: a versatile platform for in situ multipurpose functionalization , 2016 .

[41]  J. Melo,et al.  Synthesis of a low-density biopolymeric chitosan–agarose cryomatrix and its surface functionalization with bio-transformed melanin for the enhanced recovery of uranium(VI) from aqueous subsurfaces , 2016 .

[42]  Feihe Huang,et al.  Four Pillar[5]arene Constitutional Isomers: Synthesis, Crystal Structures, and Host‐Guest Complexation of Their Derivatives with Paraquat in Water , 2015 .

[43]  Yin Tian,et al.  A novel benzimidazole-functionalized 2-D COF material: synthesis and application as a selective solid-phase extractant for separation of uranium. , 2015, Journal of colloid and interface science.

[44]  Sean Xiao‐An Zhang,et al.  Pillar[5]arene‐Based Supramolecular Organic Frameworks for Highly Selective CO2‐Capture at Ambient Conditions , 2014, Advanced materials.

[45]  Yin Tian,et al.  In situ preparation of nitrogen-rich and functional ultramicroporous carbonaceous COFs by “segregated” microwave irradiation , 2014 .

[46]  M. Basan,et al.  Spectroscopic determination of U(VI) species sorbed by the Chlorella (Chlorella pyrenoidosa) fresh water algae , 2013, Journal of Radioanalytical and Nuclear Chemistry.

[47]  K. Matyjaszewski,et al.  Design and preparation of porous polymers. , 2012, Chemical reviews.

[48]  Andrew I. Cooper,et al.  Nanoporous organic polymer networks , 2012 .

[49]  D. Das,et al.  Adsorption of uranium from aqueous solution using chitosan-tripolyphosphate (CTPP) beads. , 2010, Journal of hazardous materials.

[50]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.