Covalent Organic Frameworks for Chemical and Biological Sensing
Abstract
:1. Introduction
2. Basic Principles of COF-Based Sensing
2.1. Designing a COF or COF-Based Hybird Material for Selective Adsorption
2.2. Signals Produced by the Adsorption of the Analyte
2.2.1. Fluorescence
2.2.2. Chromism
2.2.3. Capacitance and Conductivity
2.2.4. Electrochemical or Photoelectrochemical Signals
3. Application of COFs for Sensing Various Analytes
3.1. Gas Sensing
3.1.1. Acidic and Alkaline Gases
Analyte | Year | COF Names | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|---|
NH3 | 2016 | TPE−Ph−COF | Boronate | Fluorescence (turn off) | - | sub ppm level | [60] |
2018 | HMP−TAPB−1HMP−TAPB−1 | Heptazine | conductivity | 1–200 ppm | 1 ppm | [61] | |
2018 | COP−COP−1 | Triazine | Fluorescence (turn on) | - | 5.8925 × 10−4 mL/mL | [62] | |
2019 | Ph−An−COF | Boronate | Fluorescence (turn off) | - | - | [63] | |
2019 | COF−DC−8 | - | Conductivity | 2–80 ppm | 56.8–70 ppb | [64] | |
2021 | TAPB−BPDA COF | Imine | Conductivity | 5–100 ppm | 10 ppb | [65] | |
TFA | 2019 | Per−N COF | Imine | Chromism | 0.035–110 mg L−1 | 35 μg L−1 | [47] |
HCl | 2018 | COP−COP−1 | Triazine | Fluorescence (turn off) | 1.0967 × 10−4 mL/mL | [62] | |
2019 | PBHP−TAPT COF | Triazine | Chromism, conductivity | 20–3000 ppm | 20 ppm | [57] | |
2019 | COF−ETBA−DAB | Imine | Fluorescence | 4.7 ppm | [66] | ||
2020 | BCTB−BCTA COF | Imine | Fluorescence (turn off) | 1–25 mM | 10 nM | [48] | |
H2O | 2013 | TAPP−DHNDA−COF | Iminol | Chromism | 20–100% RH | [54] | |
2017 | COF−TXDBA | Boronate | Conductivity | 11–98% RH | [56] | ||
2018 | Py−TT COF | Chromism | 0.64–0.98 p/p0 | [53] | |||
2020 | TAPB−PDA−OH COF | Iminol | Chromism | [55] | |||
2021 | DUT−175 | Imine | Chromism | 33–94% RH | [67] | ||
Benzene | 2020 | BTA−TAPT-COF | Aromatic group | Capacitance | 500 ppb–100 ppm | 340 ppb | [58] |
NO2 | 2019 | COF−DC−8 | Conductivity | 2–40 ppm | 1–16 ppb | [64] | |
2020 | CON−10 | Conductivity | 2.242 ppb | [68] | |||
2020 | T−2DP | Conductivity | 0.15–5 ppm | 2.2 ppb | [69] | ||
2021 | NiPc−CoTAA | Conductivity | 1–40 ppm | [70] | |||
NO | 2019 | COF−DC−8 | Conductivity | 0.02–40 ppm | 1–5 ppb | [64] | |
H2S | 2017 | PNT−1 | Triazine, pyridine | Fluorescence (turn off) | 53 ppb | [71] | |
2019 | COF−DC−8 | Conductivity | 2–80 ppm | 121 ppb | [64] | ||
O3 | 2021 | P−COFTPB−DMTP−COF | imine | Chromism | 0.1 ppm | [72] |
3.1.2. Water Vapor (Humidity) Sensing
3.1.3. Harmful Gases Sensing
3.2. Inorganic Ions Sensing
3.2.1. Metal Ions Sensing
3.2.2. pH Sensing (H+ Sensing)
3.2.3. Inorganic Anions Sensing
3.3. Molecular Sensing
3.3.1. Explosive Sensing
3.3.2. Iodine Sensing
3.3.3. Drug Sensing
3.3.4. Small Biomolecules Sensing
3.3.5. Other Small Molecules Sensing
3.3.6. Biomacromolecule Sensing
Analyte | Year | COF/COF Hybrid Names | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|---|
Cardiac Troponin I | 2018 | TB−Au−COFs−Ab2 | Antibody | Chromism | 0.5 pg/mL–10.0 ng/mL | 0.17 pg/mL | [165] |
2021 | HRP−Ab2−Au−COF | Antibody | Chromism | 5 pg/mL–10 ng/mL | 1.7 pg/mL | [166] | |
Heat shock protein 90α | 2019 | Fe3O4@TpBD−DSS−Ab−MEG | Antibody | MS | 50 pg/mL | [167] | |
C-reactive protein | 2018 | AuNPs @COF−TPPa-1 | Antibody | Electrochemical signal (EIS, CV) | 0.017 ng/mL | 0.05–80 ng/mL | [168] |
2018 | COF−LZU8 | Antibody | Electrochemical signal (DPV) | 0.016 ng/mL | 0.05–150 ng/mL | [169] | |
2019 | p−COF | Aptamer | Photoelectrochemical signal | 0.1 ng/mL | 0.5–100 ng/mL | [174] | |
DNA | 2017 | TpTta | DNA hybridization | Fluorescence, “turn on” | 10–100 nM | 3.7 nM | [171] |
2017 | TPA−COF | DNA hybridization | Fluorescence, “turn on” | 0.02–5 nM | 20 pM | [172] | |
2018 | EB-TFP iCOF | DNA hybridization | Fluorescence, “turn on” | 0–32 mM | - | [173] | |
2021 | Cu−MOF@CuPc−TA−COF | DNA hybridization | Electrochemical signal | 1 fM–1 nM | 0.18 fM | [28] | |
Photoelectrochemical signal | 0.07 fM |
4. Challenges and Future Perspectives
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Name | Monomer 1 | Monomer 2 | Linker |
---|---|---|---|
Boronate | |||
Imine | |||
Hydrazone | |||
Maleimide | |||
Phenazine | |||
Acrylonitrile | |||
Triazine | |||
Borazine | |||
Benzimidazole | |||
Benzobisoxazole |
Analyte | Year | COF Names | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|---|
Hg2+ | 2016 | COF−LZU8 | Thioether | Fluorescence, “turn off” | - | 25.0 ppb | [42] |
2019 | Tp−Bpy NSs | AuNPs | Chromism | - | 0.33 nM | [29] | |
2020 | TFPPy−CHYD | Carbohydrazide | Fluorescence, “turn off” | 0.05 μM–4 μM | 17 nM. | [73] | |
2021 | BATHz−Bt | Carbon-carbon double bonds | Fluorescence, “turn off” | 0–27.5 mM | 26 nM | [74] | |
Cu2+ | 2016 | COF−JLU3 | Hydroxyl and azine | Fluorescence, “turn off” | 0–0.4 mM | 0.31 mM | [75] |
2017 | CTF | Triazine | Chromism | 1.0 g/L-80.0 g/L | 0.05 g/L | [50] | |
2017 | LMOP−15LMOP−15 | Tertiary amino group | Fluorescence, “turn off” | 5.1 × 10−8 M | [76] | ||
2018 | sp2c-COFs | Cyano groups | Fluorescence, “turn off” | 88 ppb | [77] | ||
2019 | QG−scaffolded COF | N atoms and hydroxyl groups | Fluorescence, “turn off” | 0.0010~10.0 μM | 0.50 nM | [78] | |
Fe3+ | 2017 | PI−COF 201 | Amino groups | Fluorescence, “turn off” | 5.0–400 μM | 0.13 μM | [79] |
PI−COF 202 | 5.0–300 μM | 0.22 μM | |||||
2019 | COF−TT | Amino groups | Fluorescence, “turn off” | 0–1.2 mM | 0.369 mM | [80] | |
2019 | TaDAP TaDA | Imine | Fluorescence, “turn off” | 0.02–0.2 mM | 18 μM | [81] | |
2019 | Bth−Dha, Bth−Dma | O,N,O′-chelating sites | Fluorescence, “turn off” | - | 0.17 μM | [82] | |
2021 | TTPE−COF | Fluorescence “turn off” | 10−8–10−2 M | 3.07 μM | [83] | ||
2021 | Tfpa−Mth COF | Hydrazide and phenol ether | Fluorescence, “turn off” and QCM | - | 64 nM | [84] | |
2021 | PMDA−TAPB | Carbonyl group | Fluorescence, “turn off” | - | - | [85] | |
Pb2+ | 2018 | TAPB-DMTP−COF | Amino groups | Electrochemical signals | 0.0050–2.0 μM | 0.0019 μmol/L | [86] |
2019 | Sulfhydryl modified TAPB−DMTTAPB−DMTTAPB−DMTP−COF | Sulfhydryl | Electrochemical signals | 0.05–20 ng·mL−1 | 0.015 ng·mL−1 | [87] | |
2021 | TAPP−COF | Photoelectrochemical signal | 0.05–1000 nM | 0.012 nM | [88] | ||
2021 | PMDA−TAPB | Amino groups | Electrochemical signals | 5–9000 nM | 1.22 nM | [85] | |
Au+ | 2018 | TTB−COF | Thioether | Fluorescence, “turn on” | 1.0–10.0 mM | 1.39 mM | [89] |
UO22+ | 2020 | TFPT−BTAN−AO | Carbon-carbon double bonds | Fluorescence, “turn off” | - | 6.7 nM | [90] |
2021 | Tph−BDP | Imines of the CT complex | Chromism | 0.18–75 μM | 0.05 μM | [91] | |
Ni2+ | 2021 | BPD−COFs | N atoms | Fluorescence, “turn off” | 0.420–1.26 × 103 pM | 68.0 pM | [92] |
Cr3+ | 2021 | CoPc−PT−COF@Cu−MOF | Bipyridine | Electrochemical signals | 10−1–105 pM | 0.0229 pM | [93] |
Pd2+ | 2021 | XB−COFs | Carbon-carbon double bonds | Fluorescence, “turn off” | - | 0.29 μM | [94] |
2021 | PY−SE−COF | Selenodiazole | Fluorescence, “turn off” | 20–450 mM | 0.45 mM | [95] |
Analyte | Year | COF/COF Hybrid Names | Specific Binding Site | Type of Detectable Signal | Detection Range | Reference |
---|---|---|---|---|---|---|
H+ | 2016 | COF−JLU4 | Amine | Fluorescence “turn off” | pH 0.9–13.0 | [100] |
2018 | COF−HQ | Quinoline | Fluorescence “turn off” | pH 1.0–5.0 | [101] | |
2019 | COFDHTA-TTA | - | Electrochemical signals | pH 3.0–11.0 | [102] | |
2021 | COF2 | Imine or triazine | Fluorescence “turn on” | pH 5.0–8.0 | [103] | |
2021 | COF−TP | Amine | Fluorescence “turn off” | pH 0–6.0 | [104] |
Analyte | Year | COF Names | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
CrO42−(Cr2O72−) | 2019 | COF−TT | Fluorescence, “turn off” | 0.343 mM | [80] | ||
MnO4− | 2019 | COF−TT | Fluorescence, “turn off” | 0.320 mM | [80] | ||
F− | 2015 | BCMP−3 | Boron sites | Fluorescence, “turn off” | [105] | ||
2018 | TFPPy−DETHz−COF | Amine | Fluorescence, “turn off” | - | 50.5 ppb | [106] | |
2018 | 2D−Fe−CTF | Triazine | Chromism | 10–100 μM | 0.56 μM | [107] | |
S2− | 2018 | TpASH | Azide | Fluorescence, “turn on” | 1 μM–5 mM | 0.12 μM | [108] |
COF Names | Year | Analyte | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|
SNW−1 | 2012 | picric acid | Fluorescence, “turn off” | 0.2–52.4 μM | 0.05 μM | [111] |
COP−2 COP−3 COP−4 | 2012 | picric acid | Fluorescence, “turn off” | - | ~1 ppm | [117] |
TNT | ~1 ppm | |||||
Py−Azine COF | 2013 | picric acid | Fluorescence, “turn off” | 0–70 ppm | - | [116] |
COF−301 COF−401 | 2015 | picric acid | Fluorescence, “turn off” | - | 1 ppm | [112] |
iPrTAPB−TFP | 2015 | picric acid | Fluorescence, “turn off” | - | 1 ppm | [118] |
TfpBDH−CONs | 2015 | picric acid | Fluorescence, “turn on/off” | - | 1 × 10−3 M | [119] |
TRIPTA | 2016 | picric acid | Fluorescence, “turn off” | - | 51.96 nM | [120] |
3D−Py−COF | 2016 | picric acid | Fluorescence, “turn off” | 0−20 ppm | - | [121] |
3′PD | 2017 | picric acid | Fluorescence, “turn off” | [115] | ||
triacetone triperoxide | ||||||
PI−CONs | 2017 | picric acid | Fluorescence, “turn off” | 0.5–10 μM | 0.25 μM | [122] |
COP−612 COP−616 | 2017 | picric acid | Fluorescence, “turn off” | - | 15 ppm | [113] |
LMOP−15 | 2017 | picric acid | Fluorescence, “turn off” | - | 0.33 μM | [76] |
iPrTAPB−Azo−COP | 2018 | picric acid | Fluorescence, “turn off” | - | 13 ppm | [123] |
1 | 2018 | picric acid | Fluorescence, “turn off” | - | 68 ppb | [124] |
CMP−LS1 CMP−LS2 | 2018 | picric acid | Fluorescence, “turn off” | - | - | [125] |
Py−TPE−COF | 2018 | picric acid | Fluorescence, “turn off” | - | 10 ppm | [126] |
DL−COF | 2019 | picric acid | Fluorescence, “turn off” | - | 13.10 ppb | [127] |
2,4-dinitrophenol | 8.56 ppb | |||||
2,4-dinitrotoluene | 10.40 ppb | |||||
4-nitrophenol | 5.15 ppb | |||||
4-nitrotoluene | 6.92 ppb | |||||
LPCMP1−4 | 2019 | TNT | Fluorescence, “turn off” | 0–100 ppm | - | [128] |
ANCOF | 2020 | Dichloran | Fluorescence, “turn off” | - | 142 ppb | [129] |
4-nitroaniline | - | 89 ppb | ||||
A−COF | 2021 | picric acid | Fluorescence, “turn off” | - | 0.09 μM | [114] |
TFPB−TTA COF | 2022 | DNP | Fluorescence, “turn off” | 50 nM–10 μM | 18 nM | [130] |
picric acid | 50 nM–12.5 μM | 16 nM |
Year | COF/COF Hybrid Names | Analyte | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|---|
2018 | TAPB−DMTTAPB−DMTP−COFs/AuNPs | Chlorogenic acid | - | Electrochemical signals (CV) | 1.0 × 10−8–4.0 × 10−5 mol L−1 | 9.5 × 10−9 mol L−1 | [140] |
2018 | 2D Fe−CTFs | Sarcosine | Sarcosine oxidase | Chromism | 10–100 μM | 0.56μM | [107] |
ochratoxin A | Aptamer | 0.2–0.8 μM | - | ||||
2019 | Py−M−COF | Enrofloxacin | Aptamer | Electrochemical signals (EIS) | 0.01 pg mL−1–2 ng mL−1 | 6.07 fg mL−1 | [49] |
Ampicillin | 0.001–1000 pg mL−1 | 0.04 fg mL−1 | |||||
2019 | QD−grafted COFs | Ferulic Acid | Molecular imprinting, amino groups | Fluorescence, “turn on” | 0.03–60 mg kg−1 | 5 μg kg−1 | [141] |
2019 | MIP/MoS2/NH2−MWCNT@COF | Sulfamerazine | Molecular imprinting | Electrochemical signals | 0.30–2.0 × 102 μM | 0.11 μM | [142] |
2019 | Ce−MOF@MCA | Oxytetracycline | Aptamer | Electrochemical signal (EIS) | 0.1–0.5 ng mL−1 | 17.4 fg/mL | [143] |
2019 | Zr−amide−Por-based 2D COF | Tetracycline | Molecular imprinting | Electrochemical signals | 5–60 pM | 2.3 pM | [144] |
2019 | Eu@TpPa−1 | Levofloxacin | Europium ions | Fluorescence, “turn off” | 10−6–10−2 M | 0.2 μM | [145] |
2019 | MIOP based on QDs−grafted COFs | Tyramine | H-bond, shape selectivity | Fluorescence, “turn on” | 35–35,000 µg/kg | 7.0 µg/kg | [146] |
SPE–HPLC | 20–2000 µg/kg | 5.0 µg/kg | |||||
2019 | NUS−30 | L-dopa | Azine | Fluorescence, “turn off” | [147] | ||
2019 | PATP@AuNPs−crosslinked MIP | Dopamine | Molecular imprinting | electrochemiluminescence | 10–14−10−6 M | 2 × 10−15 M | [148] |
2020 | UiO−66−NH2/MCA/MWCNT@rGONR | Kanamycin | Aptamer | Electrochemical signals | 25–900 nM | 13 nM | [149] |
2020 | TpPa−1@Dye | Sialic acid | Cr3+ | Fluorescence, “turn on” | 10−8–10−2 M | 7.08 × 10−9 M | [150] |
2021 | Au@COF/GO−NH2 | Chloramphenicol | Aptamer | Electrochemical signal (EIS) | 0.0001–1 ng mL-1 | 16.13 fg mL−1 | [151] |
2021 | Mg@Fe−MIL−101/TpPa−1−COF | Tetracycline | Mg2+ | Fluorescence, “turn off” | - | - | [152] |
2021 | COF−1 or COF−2 | Tetracycline | - | Fluorescence, “turn off” | 0.005−0.0625 mM | 0.002 mM | [153] |
ofloxacin | 0.025−0.25 mM | 0.0065 mM | |||||
2021 | Eu@TpPa−1 | 5-Fluorouracil | π−π stacking interactions | Fluorescence | 10−7–10−3 M | 6.45 × 10−8 M | [154] |
2018 | DAAQ−TFP | Diflubenzuron | Amino and carbonyl group (H bonding) π−π stacking interactions | HPLC | 0.2–160.0 ng mL−1 | 0.02 ng mL−1 | [155] |
Triflumuron | 0.2–160.0 ng mL−1 | 0.02 ng mL−1 | |||||
Hexaflumuron | 0.2–160.0 ng mL−1 | 0.05 ng mL−1 | |||||
Teflubenzuron | 0.2–160.0 ng mL−1 | 0.04 ng mL−1 | |||||
2019 | NH2@COF | Carboxylic acid pesticides | Amino group | HPLC-DAD | 0.2–100 ng mL−1 | 0.04–0.20 ng mL−1 | [156] |
2019 | CNs−grafted COFs@MIP | 4-ethylguaiacol | The surface of the silica matrix by acid–base pairing interactions | Fluorescence, “turn off” | 0.025–1μg ml−1 | 17 ng mL−1 | [157] |
Analyte | Year | COF/COF Hybrid Names | Specific Binding Site | Type of Detectable Signal | Detection Range | LOD | Reference |
---|---|---|---|---|---|---|---|
Glucose | 2018 | Fe−COF | Glucose oxidase | Chromism | 5–350 μM | 1.1 μM | [160] |
2019 | COFDHTA-TTA | Glucose oxidase | Electrochemical signal | 0.60 μM–6.0 mM | 0.38 μM | [102] | |
2020 | Fe−PorCOF | Glucose oxidase | Chemiluminescence | 0.01–10 μM | 5.3 nM | [161] | |
2021 | COFHD–GOX | Glucose oxidase | Chromism | 5–2000 μM | 0.54 μM | [162] | |
Uric acid | 2021 | COF−DC−8 | Hydroxyl, triazine | Electrochemical signals | 5.0–25 μM, 25–250 μM | 0.77 μM | [163] |
Ascorbic acid | 2021 | COF−DC−8 | Hydroxyl, triazine | Electrochemical signals | 30–180 μM, 0.18–1.5 μM | 12.0 μM | [163] |
Dopamine | 2021 | COF−DC−8 | Hydroxyl, triazine | Electrochemical signals | 1.0–6.0 μM, 8.0–50 μM | 0.25 μM | [163] |
GSH | 2020 | COF−300−AR | Chromism | 1–15 μM | 1.0 μM | [26] | |
2021 | Py−TT COF | Chromism | 0.4 − 60 μM | 0.225 μM | [27] |
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Zhang, S.; Liu, D.; Wang, G. Covalent Organic Frameworks for Chemical and Biological Sensing. Molecules 2022, 27, 2586. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27082586
Zhang S, Liu D, Wang G. Covalent Organic Frameworks for Chemical and Biological Sensing. Molecules. 2022; 27(8):2586. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27082586
Chicago/Turabian StyleZhang, Shiji, Danqing Liu, and Guangtong Wang. 2022. "Covalent Organic Frameworks for Chemical and Biological Sensing" Molecules 27, no. 8: 2586. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27082586