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Porous Organic Materials: Design and Applications

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Materials Chemistry".

Deadline for manuscript submissions: closed (31 July 2023) | Viewed by 24988

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Special Issue Editors

Prof. Dr. Yan’an Gao

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Guest Editor

Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou 570228, China
Interests: porous organic materials (POMs); adsorption and separation; energy storage and conversion; photoelectrocatalysis; ionic liquids

Prof. Dr. Fei Lu

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Guest Editor

Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan University, No 58, Renmin Avenue, Haikou, China
Interests: POM-based energy storage systems; ionic liquid electrolytes; nanostructured ion conductors; supramolecular self-assembly; stimuli-responsive gels

Special Issue Information

Dear Colleagues,

Learning from Nature to benefit humanity is the primary task of scientists. Porous structures are inherent to different-scale natural processes, from macroscopic honeycomb which is the ”magnum opus” of honeybees to nanopores which regulate ion/molecule transportation across the cell membrane. Inspired by the fascinating molecular pores with unique biological functions in Nature, artificial porous structures have attracted increasing research enthusiasm over the past several decades. The International Union of Pure and Applied Chemistry (IUPAC) defines a porous solid as “a solid with pores, i.e., cavities, channels, or interstices which are deeper than they are wide,” and states that these pores can be “open” or “closed”. By these definitions, porous organic materials including, but not limited to, hyper-cross-linked polymers (HCPs), polymers of intrinsic microporosity (PIMs), conjugated microporous polymers (CMPs), covalent organic frameworks (COFs), covalent triazine frameworks (CTFs), porous aromatic frameworks (PAFs), extrinsic porous molecules, and porous organic cages have been well developed. Benefiting from the diverse compositions and tunable pore topologies, porous organic materials have been considered potentially superior candidates for a wide variety of applications, such as adsorption and separation, filtration, catalysis, energy storage and conversion, mass transportation, drug delivery, etc.

This Special Issue aims to gather scientific papers on significant breakthroughs in the field of porous organic materials. We welcome papers discussing design strategies with emphasis on topology, deep insight into chemical synthesis, structure–function correlation, state-of-the-art applications, or any other relevant issues. We expect that these joint endeavors will provide insightful guidelines for the advancement of porous organic materials.

Dr. Yan’an Gao
Prof. Dr. Fei Lu
Guest Editors

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Keywords

topology design
synthesis
structure−function correlation
adsorption and separation
catalysis
energy storage and conversion
mass transportation
biological application

Published Papers (14 papers)

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14 pages, 4608 KiB

Open AccessArticle

Hexamethyldisiloxane Removal from Biogas Using a Fe₃O₄–Urea-Modified Three-Dimensional Graphene Aerogel

by Siqi Lv, Xifeng Hou, Yanhui Zheng and Zichuan Ma

Molecules 2023, 28(18), 6622; https://doi.org/10.3390/molecules28186622 - 14 Sep 2023

Viewed by 700

Abstract

Volatile methyl siloxanes (VMS), which are considered to be the most troublesome impurities in current biogas-cleaning technologies, need to be removed. In this study, we fabricated a series of Fe₃O₄–urea-modified reduced graphene-oxide aerogels (Fe₃O₄–urea–rGOAs) by using industrial-grade graphene oxide as the raw material. A fixed-bed dynamic adsorption setup was built, and the adsorption properties of the Fe₃O₄–urea–rGOAs for hexamethyldisiloxane (L2, as a VMS model pollutant) were studied. The properties of the as-prepared samples were investigated by employing various characterization techniques (SEM, TEM, FTIR, XRD, Raman spectroscopy, and N₂ adsorption/desorption techniques). The results showed that the Fe₃O₄–urea–rGOA–0.4 had a high specific surface area (188 m² g⁻¹), large porous texture (0.77 cm³ g⁻¹), and the theoretical maximum adsorption capacity for L2 (146.5 mg g⁻¹). The adsorption capacity considerably increased with a decrease in the bed temperature of the adsorbents, as well as with an increase in the inlet concentration of L2. More importantly, the spent Fe₃O₄–urea–rGOA adsorbent could be readily regenerated and showed an excellent adsorption performance. Thus, the proposed Fe₃O₄–urea–rGOAs are promising adsorbents for removing the VMS in biogas. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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14 pages, 5784 KiB

Open AccessArticle

Advanced Stimuli-Responsive Structure Based on 4D Aerogel and Covalent Organic Frameworks Composite for Rapid Reduction in Tetracycline Pollution

by Wenxin Wang, Wenjing Wang, Ying Liang, Liwen Du, Huan Yang, Haoxiang Ma, Huiting Cheng, Yaqian Yan, Yijun Shen and Qi Chen

Molecules 2023, 28(14), 5505; https://doi.org/10.3390/molecules28145505 - 19 Jul 2023

Viewed by 819

Abstract

Intelligentization of materials and structures is an important trend. Herein, the stimuli-responsive 4D aerogel is used as a smart substrate for rapid reduction in tetracycline (TC) pollution, in which this smart stimuli-responsive substrate is designated as P4D. Its fourth dimension originates from stimuli-responsive characteristics with time evolution. Meanwhile, the covalent organic frameworks (COFs) composite is constructed by BiPO₄ and triazine-based sp² carbon-conjugated g-C₁₈N₃-COF (COF-1), which is another key aspect of COF-1/BiPO₄@P4D for rapid photocatalytic degradation regarding TC pollution. This emerging smart structure of COFs@P4D can fix programmable temporary state and recover permanent state under thermal or water stimulus without any complicated equipment. Its performance can be tailored by structure, composition, and function. Compared with traditional powder-form photocatalysts, this stimuli-responsive structure provides attractive advantages, such as high permeable framework, self-adaptivity, flexibly customized functional groups, and fast reduction in TC pollution. The predictable development of COFs@P4D could draw much attention for various promising applications in pollution treatment and sensors. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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12 pages, 3974 KiB

Open AccessArticle

Interfacial Synthesis of an Ultrathin Two-Dimensional Polymer Film via [2 + 2] Photocycloaddition

by Yanqi Ban, Hui Wang, Zixuan Xiao, Lishui Sun, Qingyan Pan and Yingjie Zhao

Molecules 2023, 28(4), 1930; https://doi.org/10.3390/molecules28041930 - 17 Feb 2023

Viewed by 1744

Abstract

A carbon–carbon-linked, ultrathin, two-dimensional (2D) polymer film was prepared at the air/water interface through photochemically triggered [2 + 2] cycloaddition. The preorganization of the monomers on the water surface and the subsequent photo-polymerization led to the successful preparation of the ultrathin 2D polymer film. The obtained film is continuous, free standing, and has a large area (over 50 μm²). Transmission electron microscopy (TEM) and atomic force microscopy (AFM) give clear evidence of the ultrathin film morphology. Raman spectroscopy and X-ray photoelectron spectroscopy (XPS) indicate successful photo-induced [2 + 2] polymerization. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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10 pages, 2675 KiB

Open AccessArticle

Fluorination of Terminal Groups Promoting Electron Transfer in Small Molecular Acceptors of Bulk Heterojunction Films

by Tao Chen, Rui Shi, Ruohua Gui, Haixia Hu, Wenqing Zhang, Kangning Zhang, Bin Cui, Hang Yin, Kun Gao and Jianqiang Liu

Molecules 2022, 27(24), 9037; https://doi.org/10.3390/molecules27249037 - 18 Dec 2022

Cited by 1 | Viewed by 1757

Abstract

The fluorination strategy is one of the most efficient and popular molecular modification methods to develop new materials for organic photovoltaic (OPV) cells. For OPV materials, it is a broad agreement that fluorination can reduce the energy level and change the morphology of active layers. To explore the effect of fluorination on small molecule acceptors, we selected two non-fullerene acceptors (NFA) based bulk heterojunction (BHJ) films, involving PM6:Y6 and PM6:Y5 as model systems. The electron mobilities of the PM6:Y5 and PM6:Y6 BHJ films are 5.76 × 10⁻⁷ cm²V⁻¹s⁻¹ and 5.02 × 10⁻⁵ cm²V⁻¹s⁻¹ from the space-charge-limited current (SCLC) measurements. Through molecular dynamics (MD) simulation, it is observed that halogen bonds can be formed between Y6 dimers, which can provide external channels for electron carrier transfer. Meanwhile, the “A-to-A” type J-aggregates are more likely to be generated between Y6 molecules, and the π–π stacking can be also enhanced, thus increasing the charge transfer rate and electron mobility between Y6 molecules. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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13 pages, 1355 KiB

Open AccessArticle

Porous Organic Cage-Embedded C10-Modified Silica as HPLC Stationary Phase and Its Multiple Separation Functions

by Litao Wang, Siqi Han, Haiyang Yu, Qinghua Yu, Dong Pei, Wenjing Lv, Jiasheng Wang, Xingyu Li, Ruifang Ding, Qibao Wang and Mei Lv

Molecules 2022, 27(24), 8895; https://doi.org/10.3390/molecules27248895 - 14 Dec 2022

Cited by 1 | Viewed by 1760

Abstract

Reduced imine cage (RCC3) was covalently bonded to the surface of silica spheres, and then the secondary amine group of the molecular cage was embedded in non-polar C10 for modification to prepare a novel RCC3-C10@silica HPLC stationary phase with multiple separation functions. Through infrared spectroscopy, thermogravimetric analysis and nitrogen adsorption–desorption characterization, it was confirmed that RCC3-C10 was successfully bonded to the surface of silica spheres. The resolution of RCC3-C10@silica in reversed-phase separation mode is as high as 2.95, 3.73, 3.27 and 4.09 for p-phenethyl alcohol, 1-phenyl-2-propanol, p-methylphenethyl alcohol and 1-phenyl-1-propanol, indicating that the stationary phase has excellent chiral resolution performance. In reversed-phase and hydrophilic separation modes, RCC3-C10@silica realized the separation and analysis of a total of 70 compounds in 8 classes of Tanaka mixtures, alkylbenzene rings, polyphenyl rings, phenols, anilines, sulfonamides, nucleosides and flavonoids, and the analysis of a variety of chiral and achiral complex mixtures have been completed at the same time. Compared with the traditional C18 commercial column, RCC3-C10@silica exhibits better chromatographic separation selectivity, aromatic selectivity and polar selectivity. The multifunctional separation mechanism exhibited by the stationary phase originates from various synergistic effects such as hydrophobic interaction, π-π interaction, hydrogen bonding and steric interaction provided by RCC3 and C10 groups. This work provides flexible selectivity and application prospects for novel multi-separation functional chromatographic columns. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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11 pages, 6059 KiB

Open AccessArticle

Synthesis of a Triazaisotruxene-Based Porous Organic Polymer and Its Application in Iodine Capture

by Rong Gao, Bohang An, Cen Zhou and Xiao Zhang

Molecules 2022, 27(24), 8722; https://doi.org/10.3390/molecules27248722 - 09 Dec 2022

Cited by 5 | Viewed by 1376

Abstract

A new triazaisotruxene-based porous organic polymer (POP) was designed and successfully synthesized by a FeCl₃-promoted crosslinking reaction. As a result of its porosity and good thermal stability, the designed POP can be utilized as a promising adsorbent for iodine, not only in the gaseous phase, but also in organic and aqueous solutions. Compared to its triazatruxene (TN) analogue, the ITN-based POP shows equal iodine uptake in the gaseous phase and in hexane solution, and better uptake in aqueous solution. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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9 pages, 1577 KiB

Open AccessArticle

Ratiometric Fluorescent Sensor Based on Tb(III) Functionalized Metal-Organic Framework for Formic Acid

by Chao-Wei Zhang, Mei-Ling Li, Yi-Duo Chen, Qi Zhou and Wei-Ting Yang

Molecules 2022, 27(24), 8702; https://doi.org/10.3390/molecules27248702 - 08 Dec 2022

Cited by 3 | Viewed by 1176

Abstract

Formic acid is a common chemical raw material, the effective detection of which is of importance to food safety and environmental quality. In this work, the lanthanide functionalized dual-emission metal-organic framework (TH25) was prepared as a ratiometric fluorescent sensor for formic acid. This ratiometric sensor has a good detection performance with high selectivity, sensitivity, and reproducibility. Together with a low limit of detection of 2.1 ppm, these characters promise the ability to sense at low levels as well as a practical detection ability. This work provides ideas for the design and synthesis of effective chemical sensors for organic acids. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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13 pages, 3969 KiB

Open AccessArticle

Immobilization of Ionic Liquid on a Covalent Organic Framework for Effectively Catalyzing Cycloaddition of CO₂ to Epoxides

by Qianqian Yan, Hao Liang, Shenglin Wang, Hui Hu, Xiaofang Su, Songtao Xiao, Huanjun Xu, Xuechao Jing, Fei Lu and Yanan Gao

Molecules 2022, 27(19), 6204; https://doi.org/10.3390/molecules27196204 - 21 Sep 2022

Cited by 7 | Viewed by 2184

Abstract

Transforming CO₂ into value-added chemicals has been an important subject in recent years. The development of a novel heterogeneous catalyst for highly effective CO₂ conversion still remains a great challenge. As an emerging class of porous organic polymers, covalent organic frameworks (COFs) have exhibited superior potential as catalysts for various chemical reactions, due to their unique structure and properties. In this study, a layered two-dimensional (2D) COF, IM4F-Py-COF, was prepared through a three-component condensation reaction. Benzimidazole moiety, as an ionic liquid precursor, was integrated onto the skeleton of the COF using a benzimidazole-containing building unit. Ionization of the benzimidazole framework was then achieved through quaternization with 1-bromobutane to produce an ionic liquid-immobilized COF, i.e., BMIM4F-Py-COF. The resulting ionic COF shows excellent catalytic activity in promoting the chemical fixation of CO₂ via reaction with epoxides under solvent-free and co-catalyst-free conditions. High porosity, the one-dimensional (1D) open-channel structure of the COF and the high catalytic activity of ionic liquid may contribute to the excellent catalytic performance. Moreover, the COF catalyst could be reused at least five times without significant loss of its catalytic activity. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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13 pages, 4593 KiB

Open AccessArticle

Controllable Construction of Amino-Functionalized Dynamic Covalent Porous Polymers for High-Efficiency CO₂ Capture from Flue Gas

by Mingyue Qiu, Haonan Wu, Yi Huang, Huijuan Guo, Dan Gao, Feng Pei, Lijuan Shi and Qun Yi

Molecules 2022, 27(18), 5853; https://doi.org/10.3390/molecules27185853 - 09 Sep 2022

Cited by 1 | Viewed by 1331

Abstract

The design of high-efficiency CO₂ adsorbents with low cost, high capacity, and easy desorption is of high significance for reducing carbon emissions, which yet remains a great challenge. This work proposes a facile construction strategy of amino-functional dynamic covalent materials for effective CO₂ capture from flue gas. Upon the dynamic imine assembly of N-site rich motif and aldehyde-based spacers, nanospheres and hollow nanotubes with spongy pores were constructed spontaneously at room temperature. A commercial amino-functional molecule tetraethylenepentamine could be facilely introduced into the dynamic covalent materials by virtue of the dynamic nature of imine assembly, thus inducing a high CO₂ capacity (1.27 mmol·g⁻¹) from simulated flue gas at 75 °C. This dynamic imine assembly strategy endowed the dynamic covalent materials with facile preparation, low cost, excellent CO₂ capacity, and outstanding cyclic stability, providing a mild and controllable approach for the development of competitive CO₂ adsorbents. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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11 pages, 3172 KiB

Open AccessArticle

Covalent Organic Frameworks Composites Containing Bipyridine Metal Complex for Oxygen Evolution and Methane Conversion

by Xin Liu, Lijuan Feng, Yongpeng Li, Tian Xia, Zhuyin Sui and Qi Chen

Molecules 2022, 27(16), 5193; https://doi.org/10.3390/molecules27165193 - 15 Aug 2022

Cited by 7 | Viewed by 2214

Abstract

Novel covalent organic framework (COF) composites containing a bipyridine multimetal complex were designed and obtained via the coordination interaction between bipyridine groups and metal ions. The obtained Pt and polyoxometalate (POM)–loaded COF complex (POM–Pt@COF–TB) exhibited excellent oxidation of methane. In addition, the resultant Co/Fe–based COF composites achieved great performance in an electrocatalytic oxygen evolution reaction (OER). Compared with Co–modified COFs (Co@COF–TB), the optimized bimetallic modified COF composites (Co_0.75Fe_0.25@COF–TB) exhibited great performance for electrocatalytic OER activity, showing a lower overpotential of 331 mV at 10 mA cm⁻². Meanwhile, Co_0.75Fe_0.25@COF–TB also possessed a great turnover frequency (TOF) value (0.119 s⁻¹) at the overpotential of 330 mV, which exhibited high efficiency in the utilization of metal atoms and was better than that of many reported COF-based OER electrocatalysts. This work provides a new perspective for the future coordination of COFs with bimetallic or polymetallic ions, and broadens the application of COFs in methane conversion and electrocatalytic oxygen evolution. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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11 pages, 1660 KiB

Open AccessArticle

Synthesis of Electron-Rich Porous Organic Polymers via Schiff-Base Chemistry for Efficient Iodine Capture

by Peng Tian, Zhiting Ai, Hui Hu, Ming Wang, Yaling Li, Xinpei Gao, Jiaying Qian, Xiaofang Su, Songtao Xiao, Huanjun Xu, Fei Lu and Yanan Gao

Molecules 2022, 27(16), 5161; https://doi.org/10.3390/molecules27165161 - 12 Aug 2022

Cited by 10 | Viewed by 2170

Abstract

As one of the main nuclear wastes generated in the process of nuclear fission, radioactive iodine has attracted worldwide attention due to its harm to public safety and environmental pollution. Therefore, it is of crucial importance to develop materials that can rapidly and efficiently capture radioactive iodine. Herein, we report the construction of three electron-rich porous organic polymers (POPs), denoted as POP-E, POP-T and POP-P via Schiff base polycondensations reactions between Td-symmetric adamantane knot and four-branched “linkage” molecules. We demonstrated that all the three POPs showed high iodine adsorption capability, among which the adsorption capacity of POP-T for iodine vapor reached up to 3.94 g·g⁻¹ and the removal rate of iodine in n-hexane solution was up to 99%. The efficient iodine capture mechanism of the POP-T was investigated through systematic comparison of Fourier transform infrared spectroscopy (FT-IR), Raman spectroscopy and X-ray photoelectron spectroscopy (XPS) before and after iodine adsorption. The unique π-π conjugated system between imine bonds linked aromatic rings with iodine result in charge-transfer complexes, which explains the exceptional iodine capture capacity. Additionally, the introduction of heteroatoms into the framework would also enhance the iodine adsorption capability of POPs. Good retention behavior and recycling capacity were also observed for the POPs. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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10 pages, 2668 KiB

Open AccessArticle

Reactive Adsorption Performance and Behavior of Gaseous Cumene on MCM-41 Supported Sulfuric Acid

by Dandan Zhao, Yuheng Liu, Xiaolong Ma, Jinjin Qian and Zichuan Ma

Molecules 2022, 27(16), 5129; https://doi.org/10.3390/molecules27165129 - 11 Aug 2022

Cited by 2 | Viewed by 1231

Abstract

Efficient removal of cumene from gaseous streams and recovery of its derivatives was accomplished using a MCM-41-supported sulfuric acid (SSA/MCM-41) adsorbent. The results indicated that the removal performance of the SSA/MCM-41 for cumene was significantly influenced by the process conditions such as bed temperature, inlet concentration, bed height, and flow rate. The dose–response model could perfectly describe the collected breakthrough adsorption data. The SSA/MCM-41 adsorbent exhibited a reactive temperature region of 120–170 °C, in which the cumene removal ratios (X_c) were greater than 97%. Rising the bed height or reducing the flow rate enhanced the theoretical adsorption performance metrics, such as theoretical breakthrough time (t_B,th) and theoretical breakthrough adsorption capacity (Q_B,th), whereas increasing the inlet concentration resulted in t_B,th shortening and Q_B,th rising. As demonstrated in this paper, the highest t_B,th and Q_B,th were 69.60 min and 324.50 mg g⁻¹, respectively. Meanwhile, the spent SSA/MCM-41 could be desorbed and regenerated for cyclic reuse. Moreover, two recoverable adsorbed products, 4-isopropylbenzenesulfonic acid and 4, 4′-sulfonyl bis(isopropyl-benzene), were successfully separated and identified using FTIR and ¹H/¹³C NMR characterization. Accordingly, the relevance of a reactive adsorption mechanism was confirmed. This study suggests that the SSA/MCM-41 has remarkable potential for application as an adsorbent for the resource treatment of cumene pollutants. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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Review

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22 pages, 2620 KiB

Open AccessReview

Research on Improved MOF Materials Modified by Functional Groups for Purification of Water

by Junyan Liu and Yang Wang

Molecules 2023, 28(5), 2141; https://doi.org/10.3390/molecules28052141 - 24 Feb 2023

Cited by 5 | Viewed by 2208

Abstract

With the rapid development of urbanization and industrialization, water contamination has gradually become a big problem. Relevant studies show that adsorption is an efficient strategy to treat pollutants in water. MOFs are a class of porous materials with a three-dimensional frame structure shaped by the self-assembly of metal centers and organic ligands. Because of its unique performance advantages, it has become a promising adsorbent. At present, single MOFs cannot meet the needs, but the introduction of familiar functional groups on MOFs can promote the adsorption performance of MOFs on the target. In this review, the main advantages, adsorption mechanism, and specific applications of various functional MOF adsorbents for pollutants in water are reviewed. At the end of the article, we summarize and discuss the future development direction. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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20 pages, 4415 KiB

Open AccessReview

Beyond Pristine Metal–Organic Frameworks: Preparation of Hollow MOFs and Their Composites for Catalysis, Sensing, and Adsorption Removal Applications

by Xiaoqian Zha, Xianhui Zhao, Erin Webb, Shifa Ullah Khan and Yang Wang

Molecules 2023, 28(1), 144; https://doi.org/10.3390/molecules28010144 - 24 Dec 2022

Cited by 16 | Viewed by 2715

Abstract

Metal–organic frameworks (MOFs) have been broadly applied to numerous domains with a substantial surface area, tunable pore size, and multiple unsaturated metal sites. Recently, hollow MOFs have greatly attracted the scientific community due to their internal cavities and gradient pore structures. Hollow MOFs have a higher tunability, faster mass-transfer rates, and more accessible active sites when compared to traditional, solid MOFs. Hollow MOFs are also considered to be candidates for some functional material carriers. For example, composite materials such as hollow MOFs and metal nanoparticles, metal oxides, and enzymes have been prepared. These composite materials integrate the characteristics of hollow MOFs with functional materials and are broadly used in many aspects. This review describes the preparation strategies of hollow MOFs and their composites as well as their applications in organic catalysis, electrochemical sensing, and adsorption separation. Finally, we hope that this review provides meaningful knowledge about hollow-MOF composites and their derivatives and offers many valuable references to develop hollow-MOF-based applied materials. Full article

(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)

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