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SCIENCE CHINA Materials, Volume 62 , Issue 11 : 1655-1678(2019) https://doi.org/10.1007/s40843-019-1169-9

Recent advances in luminescent metal-organic frameworks for chemical sensors

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  • ReceivedJun 2, 2019
  • AcceptedAug 27, 2019
  • PublishedSep 17, 2019

Abstract


Funded by

the National Natural Science Foundation of China(21531005,21421001,21905142,91856124)

and the Programme of Introducing Talents of Discipline to Universities(B18030)


Acknowledgment

This work was financially supported by the National Natural Science Foundation of China (21531005, 21421001, 21905142, and 91856124), and the Programme of Introducing Talents of Discipline to Universities (B18030).


Interest statement

The authors declare that they have no conflict of interest.


Contributions statement

He J prepared the manuscript under the guidance of Li N, Bu XH. Yin J searched the references. Xu J, Li N, and Bu XH revised the manuscript. All authors contributed to the general discussion and revision of the manuscript.


Author information

Jie He received his BSc degree in chemistry in 2015 from Hexi University and MSc degree at Hubei University in 2018. Now, he is pursuing his PhD degree at the School of Materials Science and Engineering, Nankai University under the supervision of Prof. Xian-He Bu. His research interests focus on the controlled synthesis of MOFs and their applications in luminescent sensing and catalysis.


Na Li obtained her PhD degree in inorganic chemistry in 2018 from Nankai University under the supervision of Prof. Xian-He Bu. Then, she joined Prof. Bu’s group as a postdoctoral research associate at Nankai University. Her recent research focuses on the design, controlled synthesis, and applications of new porous materials.


Xian-He Bu received his BSc and PhD degrees from Nankai University in 1986 and 1992 under the supervision of Prof. Yun-Ti Chen. He was promoted to a full professor in 1995. He was a visiting professor at Tokyo University (1999), Kyoto University (2002), IMS (1998), CUHK (2002) and HKUST (2004). In 2002, he won the support of the National Outstanding Youth Foundation; in 2004, he was selected as Cheung Kong Scholar Professor by the Ministry of Education. He is now the dean of School of Materials Science and Engineering of Nankai University. His research focuses on functional coordination chemistry, MOFs, crystal engineering, molecular magnetism, etc.


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  • Figure 1

    (a) Luminescence spectra of 8 upon the addition of different metal ions in the C2H5OH solution (1 × 10−3 mol L−1). (b) Liquid luminescence spectra of 8 in different Al3+ concentrations from 1.0 × 10−5 to 1 × 10−3 mol L−1. Room temperature, λex = 324 nm. Reprinted with permission from Ref. [45]. Copyright 2016, Royal Society of Chemistry.

  • Scheme 1

    Luminescent metal-organic frameworks for a variety of sensing applications.

  • Figure 2

    (a) Detection of Hg(II) in a water medium with a functionalized MOF. (b) Schematic representation of the probable mechanism of Hg(II) sensing in UiO-66@butyne. (c) The extent of the fluorescence response of UiO-66@butyne toward various metal ions. (d) Emission spectra of UiO-66@butyne at 537 nm dispersed in water medium on incremental addition of Hg(II) solution. Reprinted with permission from Ref. [50]. Copyright 2018, American Chemical Society.

  • Figure 3

    The possible quenching mechanism for detecting CrVI by 11. Reprinted with permission from Ref. [54]. Copyright 2018, Wiley-VCH.

  • Figure 4

    (a) A space-filling diagram of the 4-fold interpenetration in 13 viewed along the crystallographic b-axis (solvent molecules and nitrate anions omitted) (left); views of the single 4-fold helical channel (right). (b) The color of activated 13 and different anion-exchanged complexes. Reprinted with permission from Ref. [57]. Copyright 2013, Royal Society of Chemistry.

  • Figure 5

    (a) 3D framework of 15 or 16 and the position of NO3 in the channels (left); I–I bonds in the channels (C, gray; N, blue; O, red; H atoms and free water molecules are omitted for clarity) (right). (b) The liquid fluorescence spectra of 15 under different concentrations of KI aqueous solution (mol L−1) upon excitation at 343 nm and the corresponding plots of intensity vs. logCI in the concentration range of 1×10−8–1×10−6 mol L−1 (inset). Reprinted with permission from Ref. [60]. Copyright 2013, Royal Society of Chemistry.

  • Figure 6

    (a) Fluorescence spectra (λex = 275 nm) of 0.2 mg mL−1 compound 17 upon the addition of fluoride with different concentrations. Inset shows photographs of the mixture solution to illustrate the color and intensity change at different concentrations of fluoride. (b) The plot of the intensity ratio of I625/I366 vs. fluoride concentration. Reprinted with permission from Ref. [63]. Copyright 2017, American Chemical Society.

  • Figure 7

    (a) Emission spectra of 18 with TbIII at 10−4, 10−5, 10−6, 10−7, and 0 mol L−1 (λex = 358 nm). (b) Relative fluorescent intensities of 5D07F2 at 545 nm for 18 dispersed in an aqueous solution containing various anions when excited at 358 nm. (c) Luminescence spectra of 18 under different concentrations of PO43− aqueous solutions. (d) The plot of the KSV curve between the luminescence intensity and PO43− concentration in an aqueous solution. Reprinted with permission from Ref. [64]. Copyright 2018, American Chemical Society.

  • Figure 8

    (a) Schematic view of the 3D framework of 20. (b) Emission spectra of 20 dispersed in DMF with the addition of 4000 ppm different organics. (c) Fluorescence titration of compound 20 dispersed in DMF with the addition of different concentrations of nitrobenzene. The excitation wavelength was 290 nm and fluorescence emission was monitored from 310 to 550 nm. (d) Fluorescence quenching percentage by nitrobenzene vapor. Inset: the results for three continuous quenching cycles. Reprinted with permission from Ref. [75]. Copyright 2014, Royal Society of Chemistry.

  • Figure 9

    (a) Fabrication of Dye@MOF composite via the “Bottle Around Ship” approach. (b) Emission spectra for Rh6G@23 at different concentrations of TNP (inset: the color changes for Rh6G@23 dispersed in solution at different levels of TNP). (c) The peak-height ratio of dye to ligand after addition of 200 ppm of various analytes. Reprinted with permission from Ref. [78]. Copyright 2018, American Chemical Society.

  • Figure 10

    (a–c) Schematic views of the structure, pore size, and hydrogen bonding of TMU-40 (Zn, Cd, and Co are a, b, and c, respectively). (d) Proposed mechanism and schematic view of the binding site for interactions of phenol derivatives by TMU-40. Hydrogen bonding and π-π interactions of MOF and guest are presented in red and cyan, respectively. Reprinted with permission from Ref. [79]. Copyright 2018, American Chemical Society.

  • Figure 11

    (a) Emission spectra of the as-synthesized 25, 25a and 25a⊃guest molecules, excited at 380 nm; inset: luminescent intensities of 25, 25a and 25a⊃guest molecules. (b) The relationship of luminescent intensities of 25a⊃guests versus emission wavelength shift compared to 25a. Reprinted with permission from Ref. [96]. Copyright 2016, Royal Society of Chemistry

  • Figure 12

    (a) The structure of compound 26. (b) The emission spectra of seven structurally similar aromatic molecules based on two emission-intensity ratios: IMOF/I[Ir]+ and IMOF/I[Ru]2+. (c) Photographic images of the emulsions of composite in different solvents under UV light irradiation at 365 nm. (d) The corresponding 2D decoded map of seven structurally similar aromatic molecules. Reprinted with permission from Ref. [101]. Copyright 2018, Royal Society of Chemistry.

  • Figure 13

    (a) The helical chain framework assembled by coordination interactions of Cd2+ ions with tib and bda2− ligands, respectively. (b) The quenching efficiencies of emission (325 nm) of 33 along with the gradual addition of ketones, λex = 275 nm. The inset represents the fluorescent emission of 33 dispersed in different solvents. (c) Fluorescent titration of 33 dispersed in water (1 mg mL−1) with the gradual addition of acetone, λex = 275 nm. Reprinted with permission from Ref. [111]. Copyright 2016, American Chemical Society.

  • Figure 14

    Illustration of guest exchange in 35 with visible color changes in different solvents, such as halobenzenes, N-heterocycles, amines, and nitroaromatic explosives. Reprinted with permission from Ref. [114]. Copyright 2015, American Chemical Society.

  • Figure 15

    (a) Process for the formation of MOF-based MMMs. (b) Illustration of nitro-functionalized MOF as a fluorescence-based “turn-on” probe for H2S. (c) The emission spectra of PVDF membrane, Al-MIL-53-NO2 MMM (30 wt%), Al-MIL-53-NO2 MMM (50 wt%), and Al-MIL-53-NO2 MMM (70 wt%) upon NaHS (1 × 10−3 mol L−1) treatment (λex = 396 nm). (d) Fluorescence spectra of Al-MIL-53-NO2 MMM (70 wt%) with increasing concentrations (0–10−3 mol L−1) of H2S. (e) The limit of detection of the various existing MOFs for the sensing of H2S. Reprinted with permission from Ref. [120]. Copyright 2018, Wiley-VCH.

  • Figure 16

    (a) Schematic representation of the optimized solvothermal preparation approach of MFM-300 (In) MOF thin film on the interdigitated electrodes. (b) Detection of SO2 in the 75 to 1000 ppb concentration range, inset: linear response for the corresponding range. (c) Linear response for MFM-300 (In) MOF-based sensor upon exposure to 500 and 1000 ppb of SO2 over 24-day period. (d) Reproducibility cycles for the detection of1000 ppb of SO2. (e) Selectivity of the MFM-300 (In) MOF sensor to other gases at 1000 ppb. Reprinted with permission from Ref. [121]. Copyright 2018, Royal Society of Chemistry.

  • Figure 17

    (a) The complete structure of LMOF-241 and emission spectra of LMOF-241 with the incremental addition of AFB1 in DCM. (b) Schematic demonstration of the electron transfer from LMOF-241 to mycotoxin LUMO, resulting in the quenched emission. Reprinted with permission from Ref. [123]. Copyright 2015, American Chemical Society.

  • Figure 18

    (a) Schematic illustration of the underlying mechanism of the selective sensing of FITC@36 towards 3-NPA. (b) Solid-state emission spectra of 36 and FITC@36 (λex = 340 nm), FITC (λex = 490 nm). (c) Emission spectra (λex = 490 nm) of FITC@36 dispersed in water after addition of five interfering substances (60 μL) and a subsequent addition of 3-NPA (60 μL). (d) The detection limit of 0.135 mol L−1 calculated via 3σ/k (k: slope, σ: standard), with a linear fitting ranging from 0 to 4.5 × 10−4 mol L−1. Reprinted with permission from Ref. [124]. Copyright 2018, American Chemical Society.

  • Figure 19

    (a) Emission spectra, (b) emission intensity ratio changes, (c) optical photographs and (d) CIE chromaticity coordinates of MLMOF-3 thin film in the presence of different analytes (20 mL, 10−4 mol L−1). Reprinted with permission from Ref. [130]. Copyright 2018, Elsevier.

  • Table 1   List of selected LMOFs, organized by sensing application, analyte, and detection mechanism

    Sensing application

    MOF

    Analyte

    Mechanism

    Ref.

    Metal cations

    [EuL1(OH)2](NO3x(solvent)

    Fe3+

    Competition absorption of excitation energy and electronic interactions

    39

    [ZnL2]·xG

    Fe3+

    Energy transfer

    40

    [Cd2Na(L3)(BDC)2.5]·9H2O/[Cd2(L3)(2,6-NDC)2]·DMF·5H2O/[Cd2(L3)(BPDC)2]·DMF·9H2O

    Fe3+

    Competition absorption of

    excitation energy and energy transfer

    41

    [NH2(CH3)2](H2O)[Zn3(BTA)(BTC)2

    4DMAC·3H2O

    Ba2+/Cu2+

    Energy transfer

    42

    [Cd2(DTP)2 (bibp)1.5]n

    Cu2+

    Charge transfer

    43

    {Zn2(O-BTC)(4,4ʹ-BPY)0.5(H2O)1.5(DMA)0.5}n

    Al3+

    Electron transfer

    45

    [Co2(dmimpym)(nda)2]n

    Al3+

    Bonding interactions and

    electron transfer

    47

    Mg-TPP-DHBDC

    Al3+

    Coordination bond interactions

    48

    [Tb4(µ6-L4)2(µ-HCOO)(µ3-OH)3(µ3-O) (DMF)2(H2O)4]n

    Ce2+

    Competition absorption of

    excitation energy, weak interactions and energy transfer

    49

    UiO-66@butyne

    Hg2+

    Molecular interactions

    50

    {[Zn(4,4ʹ-AP)(5-AIA)](DMF)0.5}n

    Hg2+

    Electrostatic interactions and electronic interactions

    51

    Anions

    {[Zn3(bpanth)(oba)3]·2DMF}n

    Cr2O72−/CrO42−

    Competitive absorption of

    excitation energy and energy transfer

    54

    Zr6O4(OH)7(H2O)3(BTBA)3

    Cr2O72−

    Charge transfer

    55

    {[Cu(pytpy)]·NO3·H2O}

    F, Cl, Br, I, N3,

    SCN, CO32−

    Ion-exchange

    57

    {Zn(L5)(OH2)2}(NO3)2·xG]n

    ClO4, BF, PF6, CF3SO3

    Ion-exchange

    59

    [Ln2Zn(L6)3(H2O)4]·(NO3)2·12H2O

    I

    Ion-exchange and energy transfer

    60

    [Tb(Mucicate)1.5·3(H2O)2]·5H2O

    CO32−

    Hydrogen bond interactions

    61

    {Tb(BTC)·(CH3OH)}

    F

    Hydrogen bond interactions

    62

    Eu-MOF

    F

    Covalent interactions and

    energy transfer

    63

    Tb@Zn-MOFs,{[Zn4(L73−)2(O2−)(H2O)2

    4EtOH}n

    PO34−

    Coordination interactions and energy transfer

    64

    Explosives

    [Zn2(bpdc)2(bpee)]

    DNT, DMNB

    Molecular interactions, bondinginteractions and electron transfer

    74

    [NH2(CH3)2]2[Cd17(L8)12(μ3-H2O)4(DMF)2(H2O)2]·solvent

    NB

    Electron transfer

    75

    [H2N(CH3)2]·Zn(NDC)(atz)·H2O

    NB

    Competitive absorption of

    excitation energy and electrontransfer

    76

    Rh6G@Zn-MOF

    TNP

    Intermolecular interactions andenergy transfer

    78

    VOCs

    Zn2(bpdc)2(bpee)

    BQ

    Electron transfer

    91

    NUS-1

    VOCs

    Molecular interactions

    95

    [Cd2(tppe)(bpdc)2(H2O)]

    Mesitylene

    Electronic interactions

    96

    Tb-MOF

    p-Xylene

    Electron transfer

    99

    Zr-BTDB-fcu-MOF

    Amine

    Hydrogen bond interactions

    100

    Ir3+/Ru2+@Zn-MOF (Me2NH2)[Zn2(L10)- (H2O)]·4DMA

    Fluorobenzene

    Host-guest interactions

    and energy transfer

    101

    Small molecules

    Cu6L116·3(H2O)(DMSO)

    Benzene, toluene

    Molecular interactions

    105

    Eu(BTC)(H2O)·1.5H2O

    DMF and acetone

    Coordination interactions

    106

    Yb(BPT)(H2O)(DMF)1.5(H2O)1.25-

    Acetone

    Coordination interactions

    107

    Tb(BTC)·G

    Acetone

    Energy transfer

    108

    [Eu2(μ2-pzdc)(μ4-pzdc)(μ2-ox)(H2O)4]·8H2O

    Acetone

    Hydrogen bond interactions

    and energy transfer

    109

    Na[Tb(OBA)2]3·0.4DMF·1.5H2O

    H2O

    Coordination interactions

    and energy transfer

    110

    [Cd2(tib)2(bda)2]·(solvent)n

    Ketones

    Competitive absorption of excitation energy and energy transfer

    111

    [Eu2L12(H2O)4]·3DMF

    DMF

    Energy transfer

    112

    [Ln2(fumarate)2(oxalate)(H2O)4]·4H2O

    H2O

    Coordination interactions

    113

    [Cu(L13)(I)]2n·2nDMF·nMeCN

    Small molecules

    Hydrogen bond interactions

    and molecular interactions

    114

    Gases

    [Zn4O(bpz)2(abdc)]·guest (MAF-X11)

    O2

    Energy transfer

    116

    MIL-100(In)⊃Tb3+, CPM-5⊃Tb3+

    O2

    Energy transfer

    117

    UiO-66@NH2

    NO

    Hydrogen bond interactions and electron transfer

    118

    Eu3+/Cu2+@UiO-66-(COOH)2

    H2S

    Bonding interactions

    and energy transfer

    119

    Al-MIL-53-NO2 MMMs

    H2S

    Molecular interactions

    120

    Bio-molecules

    LMOF-241

    Aflatoxin B1

    Electron transfer

    123

    FITC@[Cd(L14)·solvent]n

    3-Nitropropnic acid

    Energy transfer

    124

    UiO-66-NH2

    ssDNA

    Hydrogen bond interactions andenergy transfer

    125

    FeTCPP@MOF composites

    DNA

    126

    MIL-101(Cr3F(H2O)2O[(O2C)C6H4(CO2)]3·nH2O)

    HIV-1 DNA

    Electrostatic interactions and energy transfer

    127

    Ag+@Eu-MOF

    Aspartic acid

    Energy transfer

    128

    Eu-MOF

    Amino acids

    Coordination interactions

    129

    Eu0.1Tb0.9-BTC (MLMOF-3)

    Coumarin

    Hydrogen bond interactions andenergy transfer

    130

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