MIL-53
MIL-53

MIL-53 (MIL ⇒ Matériaux de l′Institut Lavoisier) belongs to the class of metal-organic framework (MOF) materials. The first synthesis and the name was established by the group of Gérard Férey in 2002.[1] The MIL-53 structure consists of inorganic [M-OH] chains, which are connected to four neighboring inorganic chains by therephthalate-based linker molecules. Each metal center is octahedrally coordinated by six oxygen atoms. Four of these oxygen atoms originate from four different carboxylate groups and the remaining two oxygen atoms belong to two different μ-OH moieties, which bridge neighboring metal centers. The resulting framework structure contains one-dimensional diamond-shaped pores. Many research group have investigated the flexibility of the MIL-53 structure. This flexible behavior, during which the pore cross-section changes reversibly, was termed 'breathing.effect' and describes the ability of the MIL-53 framework to respond to external stimuli.[2]

Structural Analogs

Monometallic single-linker MIL-53 analogs

MIL-53(Cr) was the first reported member of the MIL-53 family and is built up from Cr3+ as metal center and terephthalate (benzene-1,4-dicarboxylate) as linker molecules.[1] Based on the toolbox-like design of metal-organic framework materials, different metal centers or linker molecules can be used for the synthesis of other members of the MIL-53 family.[2] Trivalent (M3+) metal centers are mainly used, but materials with divalent (M2+) or tetravalent (M4+) metals have also been published.

Overview of reported MIL-53(M) materials
Name Metal center and

oxidation state

 Year of

publication

 Alternative

name

 Reference
MIL-53(V) V3+ 2002 MIL-47 [3][4]
V4+
MIL-53(Cr) Cr3+ 2002 [5][1]
MIL-53(Al) Al3+ 2004 [6]
MIL-53(Fe) Fe3+ 2005 [7]
Fe2+ 2005 [7]
MIL-53(In) In3+ 2005 [8]
MIL-53(Co) Co2+ 2005 MOF-71 [9][10]
MIL-53(Ga) Ga3+ 2008 [11]
MIL-53(Mn) Mn2+ 2010 [12]
MIL-53(Sc) Sc3+ 2011 [13]
MIL-53(Ni) Ni2+ 2013 [10]

Terephthalate was used as linker molecules in the early reports on MIL-53 materials.[1] Later, terephthalate-based linker molecules with additional functional groups were used for the synthesis of functionalized MIL-53 materials.[2] Apart from the two carboxylate groups of terephthalate, which are used for the formation of the framework structure, the functional linker molecules contain one or more functional groups at the benzene ring, which do not participate in the formation of the framework.

Overview of MIL-53(M) materials with functional linker molecules
Functional linker Metal center(M)
V Cr Al Fe In Ga
2-Aminoterephthalate

2-Aminobenzene-1,4-dicarboxylate

 [14] - [15][16] [17] [18] [18]
2-Fluorobenzene-1,4-dicarboxylate

2-Fluorobenzene-1,4-dicarboxylate

 [19] - [19] - - -
2-Chlorobenzene-1,4-dicarboxylate

2-Chlorobenzene-1,4-dicarboxylate

 [20] [21] [22] [23] - -
2-Bromobenzene-1,4-dicarboxylate

2-Bromobenzene-1,4-dicarboxylate

 [20] - [22] [23] [24] -
2-Iodobenzene-1,4-dicarboxylate

2-Iodobenzene-1,4-dicarboxylate

 - - [25] - - -
2-Nitrobenzene-1,4-dicarboxylate

2-Nitrobenzene-1,4-dicarboxylate

 - - [22] - [24] -
Benzene-1,2,4-tricarboxylate

Benzene-1,2,4-tricarboxylate

 - - [26] - - -
2-Methylbenzene-1,4-dicarboxylate

2-Methylbenzene-1,4-dicarboxylate

 [20] [21] [22] [23] - -
2-Trifluoromethylbenzene-1,4-dicarboxylate

2-Trifluormethylbenzene-1,4-dicarboxylate

 [20] - - - - -
2-Hydroxybenzene-1,4-dicarboxylate

2-Hydroxybenzene-1,4-dicarboxylate

 [20] - [27] - - -
2-Methoxybenzene-1,4-dicarboxylate

2-Methoxybenzene-1,4-dicarboxylate

 [20] - - - - -
2-Sulfobenzene-1,4-dicarboxylate

2-Sulfobenzene-1,4-dicarboxylate

 - - [28] - - -
2-Isocyanatebenzene-1,4-dicarboxylate

2-Isocyanatbenzene-1,4-dicarboxylate

 - - [29] - - -
2-Isothiocyanatebenzene-1,4-dicarboxylate

2-Isothiocyanatbenzene-1,4-dicarboxylate

 - - [29] - - -
2,5-Dimethylbenzene-1,4-dicarboxylate

2,5-Dimethylbenzene-1,4-dicarboxylate

 [30] - - - - -
2,5-Dihydroxybenzene-1,4-dicarboxylate

2,5-Dihydroxybenzene-1,4-dicarboxylate

 [30] - [22] [23] [24] -
2,5-Dithiolbenzene-1,4-dicarboxylate

2,5-Dithiolbenzene-1,4-dicarboxylate

 - - [31] - - -
2,5-Fluorobenzene-1,4-dicarboxylate

2,5-Difluorobenzene-1,4-dicarboxylate

 [32] - [32] - - -
2,5-Bis(trifluoromethyl)benzene-1,4-dicarboxylate

2,5-Bis(trifluormethyl)benzene-1,4-dicarboxylate

 [33] - - [23] - -
2-Amino-5-nitrobenzene-1,4-dicarboxylate

2-Amino-5-nitrobenzene-1,4-dicarboxylate

 - - [34] - [34] [34]
Benzene-1,2,4,5-tetracarboxylate

Benzene-1,2,4,5-tetracarboxylate

 - - [35]

MIL-121

 [36] MIL-82 - -
2,3,5,6-Tetramethylbenzene-1,4-dicarboxylate

2,3,5,6-tetramethylbenzene-1,4-dicarboxylate

 - [37]

MIL-105

 - - - -
2,3,5,6-Tetrachlorobenzene-1,4-dicarboxylate

2,3,5,6-Tetrachlorobenzene-1,4-dicarboxylate

 [30] - - - - -
2,3,5,6-Tetrabromobenzene-1,4-dicarboxylate

2,3,5,6-Tetrabromobenzene-1,4-dicarboxylate

 [30] - - - - -
Naphthalene-1,4-dicarboxylate

Naphthalene-1,4-dicarboxylate

 [30] - [38] - - -

Mixed-component MIL-53 analogs

Apart from monometallic single-linker MIL-53 analogs, which contain one type of metal and one type of linker within the framework structure, several mixed-component MIL-53 analogs were reported. In mixed-metal MIL-53 materials, two different metals are incorporated into the framework structure at crystallographically equivalent lattice positions. Since both type of metals occupy equivalent positions, the metal ratio can usually be changed independent from the framework structure. Mixed-metal MIL-53 analogs have been synthesized mainly by direct synthesis procedures under hydrothermal or solvothermal conditions.

Overview of mixed-metal MIL-53 analogs
Metal centers and

oxidation states

 Metal ratios

[-]

 Synthesis method Citation
Al3+ / Cr3+ 0.99 : 0.01 Direct synthesis

hydrothermal

 [39][40][41]
Al3+ / V4+ 0.99 : 0.01

0.95 : 0.05

0.71 : 0.29

0.32 : 0.68

0.13 : 0.87

 Direct synthesis

hydrothermal

 [42]
? ? [43]
Al3+ / Fe3+ 0.85 : 0.15

0.99 : 0.01

 Direct synthesis

electrochemical

 [44]
0.96 : 0.04 Post-synthetic metal-exchange
Al3+ / Ga3+ ≈ 0.70 : 0.30

≈ 0.85 : 0.15

 Direct synthesis

hydrothermal

 [45]
Cr3+ / V/4+ 0.05 : 0.95

0.10 : 0.90

0.23 : 0.77

0.50 : 0.50

0.75 : 0.25

 Direct synthesis

microwave

 [46]
0.07 : 0.93

0.13 : 0.87

0.17 : 0.83

0.37 : 0.63

0.58 : 0.42

 Direct synthesis

solvothermal

Cr3+ / Fe3+ 0.60 : 0.40 Direct synthesis

hydrothermal

 [47]
Fe2+/3+ / V2+/3+ 0.88 : 0.12

0.76 : 0.24

0.74 : 0.26

0.49 : 0.51

 Direct synthesis

solvothermal

 [48]
Fe2+ / Mn2+ 0.90 : 0.10

0.88 : 0.12

0.82 : 0.18

0.74 : 0.26

 Direct synthesis

solvothermal

 [49]
Fe2+ / Co2+ 0.97 : 0.03

0.94 : 0.06

0.90 : 0.10

Fe2+ / Ni2+ 0.91 : 0.09

0.89 : 0.11

0.84 : 0.16

0.78 : 0.22

Similar to mixed-metal MIL-53 materials, mixed-linker MIL-53 analogs have been reported, in which two different linker molecules are incorporated into the framework structure at crystallographically equivalent positions with different ratios. One benefit of using the mixed-linker concept is that the number of functional groups in the framework can be adjusted by using different linker ratios.

Overview of mixed-linker MIL-53 analogs
Linker 1 Linker 2 Linker ratios

[-]

 Metal center Synthesis method Citation
Benzene-1,4-dicarboxylate

Benzene-1,4-dicarboxylate

 2-Aminoterephthalate

2-Aminobenzene-1,4-dicarboxylate

 0.90 : 0.10

0.50 : 0.50

0.10 : 0.90

 Al3+ Direct synthesis

hydrothermal

 [50]
0.90 : 0.10

0.82 : 0.18

0.51 : 0.49

0.48 : 0.62

 [51][52][53]
Benzene-1,4-dicarboxylate

Benzene-1,4-dicarboxylate

 2,5-Dihydroxybenzene-1,4-dicarboxylate

2,5-Dihydroxybenzene-1,4-dicarboxylate

 0.75 : 0.25

0.50 : 0.50

0.25 : 0.75

 Al3+ Direct synthesis

solvothermal

 [54][55]
Benzene-1,4-dicarboxylate

Benzene-1,4-dicarboxylate

 2-Iodobenzene-1,4-dicarboxylate

2-Iodobenzene-1,4-dicarboxylate

 0.81 : 0.19

0.55 : 0.45

0.27 : 0.73

 Al3+ Direct synthesis

hydrothermal

 [25]

References

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  2. 1 2 3 Millange, Franck; Walton, Richard I. (2018-09-03). "MIL-53 and its Isoreticular Analogues: a Review of the Chemistry and Structure of a Prototypical Flexible Metal-Organic Framework". Israel Journal of Chemistry. 58 (9–10): 1019–1035. doi:10.1002/ijch.201800084. S2CID 105480508.
  3. ↑ Karin Barthelet, Jérôme Marrot, Didier Riou, Gérard Férey (2002), "A Breathing Hybrid Organic–Inorganic Solid with Very Large Pores and High Magnetic Characteristics", Angewandte Chemie International Edition (in German), vol. 41, no. 2, pp. 281–284, doi:10.1002/1521-3773(20020118)41:2<281::AID-ANIE281>3.0.CO;2-Y, ISSN 1521-3773, PMID 12491409{{citation}}: CS1 maint: multiple names: authors list (link)
  4. ↑ Hervé Leclerc, Thomas Devic, Sabine Devautour-Vinot, Philippe Bazin, Nathalie Audebrand (2011-10-13), "Influence of the Oxidation State of the Metal Center on the Flexibility and Adsorption Properties of a Porous Metal Organic Framework: MIL-47(V)", The Journal of Physical Chemistry C (in German), vol. 115, no. 40, pp. 19828–19840, doi:10.1021/jp206655y, ISSN 1932-7447{{citation}}: CS1 maint: multiple names: authors list (link)
  5. ↑ C. Serre, F. Millange, C. Thouvenot, M. Noguès, G. Marsolier, D. Louër, and G. Férey: Very Large Breathing Effect in the First Nanoporous Chromium(III)-Based Solids: MIL-53 or CrIII(OH)·{O2C-C6H4-CO2}·{HO2C-C6H4-CO2H}x·H2Oy. In: J. Am. Chem. Soc. 2002, 124, 45, S. 13519–13526, doi:10.1021/ja0276974.
  6. ↑ Loiseau, Thierry; Serre, Christian; Huguenard, Clarisse; Fink, Gerhard; Taulelle, Francis; Henry, Marc; Bataille, Thierry; Férey, Gérard (2004-03-19). "A Rationale for the Large Breathing of the Porous Aluminum Terephthalate (MIL-53) Upon Hydration". Chemistry - A European Journal. 10 (6): 1373–1382. doi:10.1002/chem.200305413. ISSN 0947-6539. PMID 15034882.
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  12. ↑ Guohai Xu, Xiaoguang Zhang, Peng Guo, Chengling Pan, Hongjie Zhang (2010-03-24), "Mn II -based MIL-53 Analogues: Synthesis Using Neutral Bridging μ 2 -Ligands and Application in Liquid-Phase Adsorption and Separation of C6−C8 Aromatics", Journal of the American Chemical Society (in German), vol. 132, no. 11, pp. 3656–3657, doi:10.1021/ja910818a, ISSN 0002-7863, PMID 20196605{{citation}}: CS1 maint: multiple names: authors list (link)
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  14. ↑ Karen Leus, Sarah Couck, Matthias Vandichel, Gauthier Vanhaelewyn, Ying-Ya Liu (2012), "Synthesis, characterization and sorption properties of NH2-MIL-47", Physical Chemistry Chemical Physics (in German), vol. 14, no. 44, p. 15562, Bibcode:2012PCCP...1415562L, doi:10.1039/c2cp42137b, ISSN 1463-9076, PMID 23073025{{citation}}: CS1 maint: multiple names: authors list (link)
  15. ↑ Tim Ahnfeldt, Daniel Gunzelmann, Thierry Loiseau, Dunja Hirsemann, Jürgen Senker (2009-04-06), "Synthesis and Modification of a Functionalized 3D Open-Framework Structure with MIL-53 Topology", Inorganic Chemistry (in German), vol. 48, no. 7, pp. 3057–3064, doi:10.1021/ic8023265, hdl:10536/DRO/DU:30064444, ISSN 0020-1669, PMID 19245258{{citation}}: CS1 maint: multiple names: authors list (link)
  16. ↑ Tim Ahnfeldt, Nathalie Guillou, Daniel Gunzelmann, Irene Margiolaki, Thierry Loiseau (2009-06-29), "[Al 4 (OH) 2 (OCH 3 ) 4 (H 2 N-bdc) 3 ]⋅ x H 2 O: A 12-Connected Porous Metal-Organic Framework with an Unprecedented Aluminum-Containing Brick", Angewandte Chemie International Edition (in German), vol. 48, no. 28, pp. 5163–5166, doi:10.1002/anie.200901409, PMID 19504512{{citation}}: CS1 maint: multiple names: authors list (link)
  17. ↑ Sebastian Bauer, Christian Serre, Thomas Devic, Patricia Horcajada, Jérôme Marrot (2008-08-06), "High-Throughput Assisted Rationalization of the Formation of Metal Organic Frameworks in the Iron(III) Aminoterephthalate Solvothermal System", Inorganic Chemistry (in German), vol. 47, no. 17, pp. 7568–7576, doi:10.1021/ic800538r, ISSN 0020-1669, PMID 18681423{{citation}}: CS1 maint: multiple names: authors list (link)
  18. 1 2 Pablo Serra-Crespo, Elena Gobechiya, Enrique V. Ramos-Fernandez, Jana Juan-Alcañiz, Alberto Martinez-Joaristi (2012-09-04), "Interplay of Metal Node and Amine Functionality in NH 2 -MIL-53: Modulating Breathing Behavior through Intra-framework Interactions", Langmuir (in German), vol. 28, no. 35, pp. 12916–12922, doi:10.1021/la302824j, ISSN 0743-7463, PMID 22891682{{citation}}: CS1 maint: multiple names: authors list (link)
  19. 1 2 Shyam Biswas, Tom Rémy, Sarah Couck, Dmytro Denysenko, Geert Rampelberg (2013), "Partially fluorinated MIL-47 and Al-MIL-53 frameworks: influence of functionalization on sorption and breathing properties", Physical Chemistry Chemical Physics (in German), vol. 15, no. 10, p. 3552, Bibcode:2013PCCP...15.3552B, doi:10.1039/c3cp44204g, ISSN 1463-9076, PMID 23381460{{citation}}: CS1 maint: multiple names: authors list (link)
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  22. 1 2 3 4 5 Shyam Biswas, Tim Ahnfeldt, Norbert Stock (2011-10-03), "New Functionalized Flexible Al-MIL-53-X (X = -Cl, -Br, -CH 3, -NO 2, -(OH) 2 ) Solids: Syntheses, Characterization, Sorption, and Breathing Behavior", Inorganic Chemistry (in German), vol. 50, no. 19, pp. 9518–9526, doi:10.1021/ic201219g, ISSN 0020-1669, PMID 21899293{{citation}}: CS1 maint: multiple names: authors list (link)
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  32. 1 2 Shyam Biswas, Sarah Couck, Dmytro Denysenko, Asamanjoy Bhunia, Maciej Grzywa (2013-11-15), "Sorption and breathing properties of difluorinated MIL-47 and Al-MIL-53 frameworks", Microporous and Mesoporous Materials (in German), vol. 181, pp. 175–181, doi:10.1016/j.micromeso.2013.07.030{{citation}}: CS1 maint: multiple names: authors list (link)
  33. ↑ Claudia Zlotea, Delphine Phanon, Matjaz Mazaj, Daniela Heurtaux, Vincent Guillerm (2011), "Effect of NH2 and CF3 functionalization on the hydrogen sorption properties of MOFs", Dalton Transactions (in German), vol. 40, no. 18, p. 4879, doi:10.1039/c1dt10115c, ISSN 1477-9226, PMID 21431158{{citation}}: CS1 maint: multiple names: authors list (link)
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  35. ↑ Christophe Volkringer, Thierry Loiseau, Nathalie Guillou, Gérard Férey, Mohamed Haouas (2010-10-05), "High-Throughput Aided Synthesis of the Porous Metal−Organic Framework-Type Aluminum Pyromellitate, MIL-121, with Extra Carboxylic Acid Functionalization", Inorganic Chemistry (in German), vol. 49, no. 21, pp. 9852–9862, doi:10.1021/ic101128w, ISSN 0020-1669, PMID 20923169{{citation}}: CS1 maint: multiple names: authors list (link)
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