Chemically reprogrammable metal organic frameworks (MOFs) based on Diels–Alder chemistry

Nayab, Sana; Trouillet, Vanessa; Gliemann, Hartmut; Hurrle, Silvana; Weidler, Peter G.; Tariq, Saadia R.; Goldmann, Anja S.; Barner‐Kowollik, Christopher; Yameen, Basit

doi:10.1039/c7cc06150a

Cited by 19 publications

(19 citation statements)

References 42 publications

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“…However, the presence of Br − did not affect the DA ligations. 18 Similarly, the signal at 399.7 eV 48 corresponding to the N 1s orbital corroborates the presence of amino groups within the framework of NH 2 -MIL-53-Al (Table S4). Furthermore, the subsequent grafting of bromo moieties into the MOF structure was ascertained by the appearance of a peak at 70.1 eV 38 (Br 3d 5/2 ), attributed to the bromine covalently attached to carbon Finally, the different reaction steps of PSM of IRMOF-3-Zn were investigated through XPS analysis.…”

Section: ■ Results and Discussionsupporting

confidence: 60%

Reversible Diels–Alder and Michael Addition Reactions Enable the Facile Postsynthetic Modification of Metal–Organic Frameworks

et al. 2021

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Functionalization of metal−organic frameworks (MOFs) is critical in exploring their structural and chemical diversity for numerous potential applications. Herein, we report multiple approaches for the tandem postsynthetic modification (PSM) of various MOFs derived from Zr(IV), Al(III), and Zn(II). Our current work is based on our efforts to develop a wide range of MOF platforms with a dynamic functional nature that can be chemically switched via thermally triggered reversible Diels−Alder (DA) and hetero-Diels−Alder (HDA) ligations. Furan-tagged MOFs (furan-UiO-66-Zr) were conjugated with maleimide groups bearing dienophiles to prepare MOFs with a chemically switchable nature. As HDA pairs, phosphoryl dithioester-based moieties and cyclopentadiene (Cp)-grafted MOF (Cp-MIL-53-Al) were utilized to demonstrate the cleavage and rebonding of the linkages as a function of temperature. In addition to these strategies, the Michael addition reaction was also applied for the tandem PSM of IRMOF-3-Zn. Maleimide groups were postsynthetically introduced in the MOF lattice, which were further ligated with cysteine-based biomolecules via the thiol− maleimide Michael addition reaction. On the basis of the versatility of the herein presented chemistry, we expect that these approaches will help in designing a variety of sophisticated functional MOF materials addressing diverse applications.

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Section: ■ Results and Discussionsupporting

confidence: 60%

Reversible Diels–Alder and Michael Addition Reactions Enable the Facile Postsynthetic Modification of Metal–Organic Frameworks

et al. 2021

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“…In the post-synthetic modification of MOFs, lots of functional groups were successfully grafted into/onto pristine MOFs by the azide-alkyne 1,3-dipolar cycloaddition toward targeted applications. In addition to the azide-alkyne 1,3-dipolar cycloaddition, other click reactions, such as Diels-Alder click reaction and thiol−ene click reaction, have also been employed as effective reactions in the MOF construction and modification [207,[252][253][254][255][256][257]. The versatile click chemistry through both ligand pre-design and post-synthetic modification not only makes the MOF preparation easy, but also broadens their applications by integrating functional groups into the MOF networks.…”

Section: Discussionmentioning

confidence: 99%

Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks

Wang

Zhao

2019

Coordination Chemistry Reviews

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“…Metal-organic frameworks (MOFs) are porous coordination polymers that have been extensively explored for their framework flexibility and functionality. [1][2][3][4][5][6][7][8][9][10][11] Proper modulation of organic linkers and metal clusters can provide unlimited MOF materials for a variety of applications. [4,5,8,12] Therefore, MOFs are often studied for their potential applications in catalysis, sensing, adsorption, separation, and drug delivery.…”

Section: Introductionmentioning

confidence: 99%

“…[4,5,8,12] Therefore, MOFs are often studied for their potential applications in catalysis, sensing, adsorption, separation, and drug delivery. [2] Iron-based metal-organic frameworks, for instance, may exhibit heterogeneous Fenton-like behavior that is important for environment remediation. [9,[13][14][15][16][17][18][19] Amino-functionalized iron terephthalate compound (NH 2 -MIL-88B) is an amino-functionalized iron-based metal-organic framework that comprises ferric (Fe 3+ ) octahedral dimers and 2-amino terephthalic acid, which result in a framework with high porosity and enormous surface area.…”

Section: Introductionmentioning

confidence: 99%

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Graphene oxide incorporated amino‐functionalized iron terephthalate composite as a heterogeneous Fenton‐like catalyst

Liew

Nguang

Minggu

et al. 2021

J Chinese Chemical Soc

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Amino-functionalized iron terephthalate metal-organic framework (NH 2 -MIL-88B) has been studied for its adsorption and catalytic properties due to its high surface area and unique topological architecture. Functionality of the material can be improved through surface modification to increase active sites for the targeted applications. In this study, graphene oxide (GO) was incorporated to the NH 2 -MIL-88B material to obtain composite with improved adsorption and catalytic properties. The results showed that GO/NH 2 -MIL-88B in dark (as GO/NH 2 -MIL-88B/Dark system) was capable to adsorb 28.1% of methylene blue (MB) in water, which is about twice the adsorption of MB by the NH 2 -MIL-88B material in dark (as NH 2 -MIL-88B/Dark system). Furthermore, with the presence of hydrogen peroxide (H 2 O 2 ), the GO/NH 2 -MIL-88B composite in dark condition (as GO/NH 2 -MIL-88B/H 2 O 2 /Dark) and the GO/NH 2 -MIL-88B composite under ultraviolet-A (UV-A) irradiation (as GO/NH 2 -MIL-88B/

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Chemically reprogrammable metal organic frameworks (MOFs) based on Diels–Alder chemistry

Abstract: We pioneer a new class of reprogrammable MOFs able to switch their interlattice chemistry via a facile Diels–Alder based cycloreversion process.

Cited by 19 publications

References 42 publications

Reversible Diels–Alder and Michael Addition Reactions Enable the Facile Postsynthetic Modification of Metal–Organic Frameworks

Reversible Diels–Alder and Michael Addition Reactions Enable the Facile Postsynthetic Modification of Metal–Organic Frameworks

Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks

Graphene oxide incorporated amino‐functionalized iron terephthalate composite as a heterogeneous Fenton‐like catalyst

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