Application of Hydrogen-Bonded Organic Frameworks in Environmental Remediation: Recent Advances and Future Trends
Abstract
:1. Introduction
2. Design Rules of Stable HOFs
2.1. Stronger Intermolecular Interactions
2.2. Rigid Stereoscopic Framework
2.3. Highly Interpenetrated Networks
2.4. Additional Intermolecular Interaction
2.5. Avoiding D/A Structure
3. Supramolecular Synthons for Designing HOFs
3.1. DAT Synthons
3.2. Carboxylic Acid Synthons
3.3. Pyridine Synthons
3.4. Sulfonate-Guanidium Sheet Synthons
3.5. Carboxyl-Pyridine Dimer Synthons
4. HOFs Modification/HOF-Derived Materials
4.1. Metallized HOFs
4.1.1. Metallized HOFs Containing Metal-Organic Cations
4.1.2. Metallized HOFs Containing Metal-Organic Anions
4.1.3. Metallized HOFs Containing Neutral Metal-Organic Complexes
4.1.4. Hybrid HOFs Containing Metal-Porphyrin Complexes
4.2. HOF-Derived Materials
4.2.1. HOF Composites
4.2.2. HOF-Derived Pyrolytic Materials
5. Applications of HOFs in Environmental Remediation
5.1. Gas Adsorption and Separation
5.1.1. CO2/CH4 and CO2/N2 Separation
5.1.2. C2H2/C2H4 and C2H4/C2H6 Separation
5.1.3. C2H2/CO2 Separation
5.1.4. NH3 Capture
5.1.5. Xe/Kr Separation
5.2. Adsorption in Aqueous Solution
5.2.1. Metal Ion Adsorption
5.2.2. Adsorption of Organic Contaminants
5.3. Catalysis
5.3.1. Energy Conversion
5.3.2. Degradation of Pollutants
5.4. Sensor Applications
6. Conclusions
- Functionalization brings additional functionality to the HOFs’ holes. Due to the periodic network chemical structure of HOFs, different functional groups, such as aromatic and aliphatic groups, esters, carboxylic acids, and alcohols, can be selected to pre-design the structure of HOFs, so as to achieve the purpose of precise regulation of its structure and properties. Various functional groups allow HOFs to be applied in specific areas, such as increasing the interaction of HOFs with pollutants to remove them from gases or solutions;
- With the development of computer technology, molecular simulation technology has been widely used in the mechanism study of some materials, which can not only clarify the interaction between adsorbent and adsorption sites on the inner surface of adsorbent channels qualitatively, but also obtain quantitative results. Compared with traditional experimental methods, molecular simulation has the advantages of convenience and speed, and can obtain microscopic information which is difficult to obtain in conventional experiments. Therefore, molecular simulation technology can be hoped to screen whether HOFs have adsorption properties for specific pollutants, and explain the adsorption mechanism at the molecular level;
- HOFs need to be extended beyond traditional water and air pollution to cover new frontiers, such as the remediation of contaminated land (soil). Remediation of contaminated soil is an urgent environmental problem. If not dealt with effectively, it will seriously destroy the whole ecosystem and endanger human health through the biological chain. HOFs can be used to separate pollutants from the soil by adsorption, or reduce pollutants to dissoluble states by chemical reducing agents, thus reducing the migration and bioavailability of pollutants in the soil environment;
- Through DFT high-throughput computing and machine learning, we hoped to build predictive single objective/multi-objective nature-oriented HOFs intelligent platforms to develop low-cost and efficient HOFs to remove pollutants from the environment and facilitate their large-scale application.
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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Supramolecular Synthons | Construction Component | Hydrogen Bonding Mode | Numbers of Hydrogen Bond Type | Chemical Stability |
---|---|---|---|---|
DAT | Single-component | N—H···N | 3 | Good |
Carboxylic acid | Single-component | O—H···O | 1 | Good |
Pyridine | Single-component | N—H···N | 1 | Good |
Sulfonate-guanidium sheet | Two-component | N—H···O—S | 2 | Sulfonic acid is unstable |
Carboxyl-pyridine dimer | Two-component | O—H···N and O···H—C | 1 | Good |
Materials | Guest Species/Other Materials | Porosity | Obtaining Property | |
---|---|---|---|---|
Metallized HOFs | Metal-organic cations | [M(H2O)6]n+ (n = 1, 2, 3···); [M(NH3)6]n+; [M(en)3]n+; [M(tame)2]n+; [M(lmdz)6]n+; Metal-organic cage | Microporous | Oxidation-reduction; Electronics; Optics; Magnetism |
Metal-organic anions | [M(CN)n]m−) (n = 2, 3, 4···; m = 1, 2, 3···); [M(C2O4)n]m− | |||
Neutral metal-organic complexes | Metal salt hydrate | |||
Metal-porphyrin complexes | Metal centers of porphyrins and their derivatives | |||
HOF composites | Nanoparticles; Metal oxides; Polymers; Carbon materials | Micro/mesoporous | Catalysis; Adsorption; Photothermal | |
HOF-derived pyrolytic materials | Heteroatoms | Micro/mesoporous | Oxidation-reduction; Adsorption |
HOFs | Pore Size/Å | BET Surface Areas (m2·g−1) | Functionality | Ref. |
---|---|---|---|---|
SOF-1a | 7.4 | 474 | CO2/C2H2 adsorption | [99] |
Trispyrazole-1 | 16.5 | 1159 | fluorocarbon and hydrocarbon adsorption | [51] |
PFC-2 | 19.7, 10.7 | 1014 | C2H2/C2H4 separation | [100] |
HOF-14 | 31.2 × 24.1 | 2573 | hydrocarbon separation | [101] |
HOF-102 | 34.0 × 35.58 | 2500 | mustard gas detoxification | [102] |
benzotrisimidazole-CF3 | 3.8 | 131 | O2/Ar, O2/N2 separatio | [103] |
HOF-16a | 6.7 | 279 | C3H6/C3H8 separation | [26] |
IISERP-HOF1 | 9.4 × 9.1 | 1025 | CO2/N2 separation | [104] |
HOF-9a | 6.9 × 8.8 | 286 | CO2/N2 separation | [105] |
HOF-8d | 6.8 × 4.5 | - | CO2 capture | [32] |
CP-PP-1a | 18.1 × 30.3 | 114 | CO2/N2 separation | [106] |
HOF-5a | 3.9 × 5.5 | 1101 | CO2 capture | [36] |
PFC-5 | 5.2 × 4.0 | 256 | hydrocarbon separation | [107] |
HOF-76a | 7.0 | 1121 | C2H6/C2H4 separation | [108] |
HOF-6a | ~6.4, ~7.5 | 130 | CO2/N2 separation | [109] |
HOF-7a | 3.4 × 4.7, 4.2 × 6.7 | 124 | CO2/N2 separation | [110] |
HOF-11a | 6.2 × 6.8 | 687 | CO2 capture | [55] |
HOF-FJU-1a | 3.4 × 5.3 | 385 | C2H6/C2H4 separation | [111] |
Tcpb/HOF-BTB | 18.5 | 1095 | CO2/CH4,CO2/N2 separation | [112] |
PFC-11 | - | 751.3 | CO2, benzene and toluene capture | [52] |
PFC-12 | - | 653.6 | CO2, benzene and toluene capture | [52] |
HOF-12a | 8.6 × 10.8 | 320 | CO2 capture | [113] |
ZJU-HOF-1 | 4.6 | 1465 | C2H6/C2H4 separation | [114] |
HOF-40 | 4.15 × 3.85 | 234 | Xe/Kr separation | [115] |
HOF-30a | ~4.2 | 361 | propyne/propylene separation | [60] |
HOF-TCBP | 17.8 × 26.3 | 2066 | light hydrocarbons separation | [53] |
ZJU-HOF-10 | 14.07 × 16.73 | 1169 | C2H6/C2H4 separation | [116] |
HOF-4a | 3.8 × 8.1 | 312 | C2H6/C2H4 separation | [117] |
UPC-HOF-6 | ~2.8 | 237 | H2/N2 separation | [118] |
SOF-7a | 13.5 × 14.0 | 900 | CO2/CH4 separation | [65] |
CPOS-5 | 5.3 | 760 | CO2 capture | [119] |
Absorbent | T (K) | P (Bar) | C2H6 UptakeMixed (mmol·g−1) | C2H4 UptakeMixed (mmol·g−1) | IAST Selectivity (C2H6/C2H4) | Ref. |
---|---|---|---|---|---|---|
ZJU-HOF-1 | 298 | 1 | 3.2 | 1.42 | 2.25 | [114] |
MFU-15 | 293 | 1 | 3.13 | 1.6 | 1.96 | [130] |
PCN-250 | 298 | 1 | 2.96 | 1.6 | 1.85 | [132] |
Ni(bcd)(ted)0.5 | 298 | 1 | 2.48 | 1.38 | 1.8 | [133] |
IRMOF-8 | 298 | 1 | 2.16 | 1.25 | 1.7 | [134] |
MAF-49 | 316 | 1 | 1.21 | 0.44 | 2.7 | [134] |
Fe2(O)2(dobdc) | 298 | 1 | 2.53 | 0.57 | 4.4 | [135] |
MIL-142-A | 298 | 1 | 2.1 | 1.39 | 1.51 | [136] |
PCN-245 | 298 | 1 | 1.8 | 1 | 1.8 | [137] |
Cu(Qc)2 | 298 | 1 | 1.65 | 0.48 | 3.45 | [138] |
ZIF-8 | 275 | 1 | 1.26 | 0.7 | 1.8 | [139] |
ZIF-7 | 298 | 1 | 1.2 | 0.8 | 1.5 | [140] |
Materials | Adsorbent | pH | Qm (mg·g−1) | Ref. |
---|---|---|---|---|
HOFs | CSMCRIHOF-1 | 7 | 1185 | [156] |
MOFs | Cu-BTC | 3 | 617 | [157] |
MIL-101-His | 6 | 345 | [158] | |
UIO-66-AO | 5.5 | 106 | [159] | |
ZIF-67 | 4 | 397.6 | [160] | |
ZIF-90-OM | 5 | 482.5 | [161] | |
COFs | COF-PDAN-AO | 4 | 256 | [162] |
COF-TpPa-1 | 6 | 120 | [163] | |
DP-COF | 4.5 | 317 | [164] | |
ACOF | 4.5 | 169 | [165] | |
TPB-BPTA-COF-AO | 7 | 90.6 | [166] | |
Inorganic | CMLH | 6 | 99 | [167] |
Fe3O4@SiO2 composites | 6 | 52.36 | [168] | |
PFG MSs | 8 | 207.6 | [169] | |
Organic | PAMAMG3-SDB | 6 | 99.05 | [170] |
CTPP | 5 | 140 | [171] | |
HCP-2 | 8 | 33.4 | [172] | |
Biology | Ca-pretreated cystoseira indica alga | 4 | 318.15 | [173] |
Bacillus cereus 12-2 | 5 | 94.14 | [174] | |
Biosynthesized melanin | 5 | 49 | [175] |
Materials | Absorbent | Dye | Qm (mg·g−1) | Ref. |
---|---|---|---|---|
HOFs | PFC-1 | RhB | 317 | [181] |
PFC-1 | MO | 252 | [181] | |
MOFs | NMIL-100(Fe) | RhB | 76.69 | [184] |
Ni@MOF-74(Ni) | RhB | 177.8 | [185] | |
UiO-66-NH2 | MO | 148.4 | [186] | |
ZIF-67 | MO | 16.3 | [187] | |
MIL-68(Al)/GO | MO | 400 | [188] | |
COFs | TFP-PPDA | RhB | 704.3 | [189] |
CX4-BD-2 | RhB | 40 | [190] | |
CuP-DMNDA-COF/Fe | RhB | 378 | [191] | |
Benzodiimidazole-COF | MO | 256 | [192] | |
P-TH COF | MO | 25.9 | [193] |
Materials | Reaction | Performance | Ref. |
---|---|---|---|
PFC-42 | H2O Photocatalysis | H2 production rate (2265 μmol·g−1·h−1 ) | [195] |
TBAP-α | H2O Photocatalysis | H2 production rate (3108 mmol·g−1·h−1) | [196] |
PFC-72-Co | CO2 Photocatalysis | CO production rate (14.7 μmol·g−1·h−1 ) | [29] |
PFC-73-Ni | CO2 Photocatalysis | CO production rate (9.8 μmol·g−1·h−1 ) | [29] |
PFC-73-Cu | CO2 Photocatalysis | CO production rate (4.4 μmol·g−1·h−1 ) | [29] |
PFC-58 | CO2 Photocatalysis | CO production rate (3.2 μmol·g−1·h−1 ) | [86] |
PFC-58-61 | CO2 Photocatalysis | CO production rate (4.6 μmol·g−1·h−1 ) | [86] |
PFC-58-30 | CO2 Photocatalysis | CO production rate (7.3 μmol·g−1·h−1 ) | [86] |
HOF-25-Re | CO2 Photocatalysis | CO production rate (1448 μmol·g−1·h−1 ) | [197] |
Pt@nano-HOF | H2O Photocatalysis | H2 production rate (1480 μmol·g−1·h−1 ) | [31] |
PFC-1/CNNS | H2O Photocatalysis | H2 production rate (4450 μmol·g−1·h−1) | [38] |
PFC-45/Cu2O@CP | CO2 Photocatalysis | CO production rate (11.81 μmol·g−1·h−1 ) | [87] |
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Zhang, Y.; Tian, M.; Majeed, Z.; Xie, Y.; Zheng, K.; Luo, Z.; Li, C.; Zhao, C. Application of Hydrogen-Bonded Organic Frameworks in Environmental Remediation: Recent Advances and Future Trends. Separations 2023, 10, 196. https://doi.org/10.3390/separations10030196
Zhang Y, Tian M, Majeed Z, Xie Y, Zheng K, Luo Z, Li C, Zhao C. Application of Hydrogen-Bonded Organic Frameworks in Environmental Remediation: Recent Advances and Future Trends. Separations. 2023; 10(3):196. https://doi.org/10.3390/separations10030196
Chicago/Turabian StyleZhang, Yu, Mengfei Tian, Zahid Majeed, Yuxin Xie, Kaili Zheng, Zidan Luo, Chunying Li, and Chunjian Zhao. 2023. "Application of Hydrogen-Bonded Organic Frameworks in Environmental Remediation: Recent Advances and Future Trends" Separations 10, no. 3: 196. https://doi.org/10.3390/separations10030196