Tandem post-synthetic modification for functionalized metal–organic frameworks via epoxidation and subsequent epoxide ring-opening

Hindelang, Konrad; Vagin, Sergei I.; Anger, Christian A.; Rieger, Bernhard

doi:10.1039/c2cc16949e

Cited by 32 publications

(21 citation statements)

References 17 publications

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“…Recently, we published a procedure for the epoxidation of (Scheme 4). [15] Beside the epoxidation, the osmium tetroxide (OsO 4 )-catalyzed dihydroxylation is another common oxidation reaction to introduce functional groups through C=C double bonds. OsO 4 is well soluble in organic solvents, air and moisture resistant and has a small molecular diameter (OsÀO bond length: 1.7 ).…”

Section: Resultsmentioning

confidence: 99%

Functionalization of Metal–Organic Frameworks through the Postsynthetic Transformation of Olefin Side Groups

Hindelang

Kronast

Vagin

et al. 2013

Chemistry A European J

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For the first time, the adaptability of the C=C double bond as a versatile precursor for the postsynthetic modification (PSM) of microporous materials was extensively investigated and evaluated. Therefore, an olefin-tagged 4,4'-bipyridine linker was synthesized and successfully introduced as pillar linker within a 9,10-triptycenedicarboxylate (TDC) zinc paddle-wheel metal-organic framework (MOF) through microwave-assisted synthesis. Different reactions, predominately used in organic chemistry, were tested, leading to the development of new postsynthetic reactions for the functionalization of solid materials. The postsynthetic oxidation of the olefin side groups applying osmium tetroxide (OsO₄) as a catalyst led to the formation of a microporous material with free vicinal diol functionalities. The epoxidation with dimethyldioxirane (DMDO) enabled the synthesis of epoxy-functionalized MOFs. In addition to that, reaction procedures for a postsynthetic hydroboration with borane dimethyl sulfide as well as a photoinduced thiol-ene click reaction with ethyl mercaptan were developed. For all of these PSMs, yields of more than 90% were obtained, entirely maintaining the crystallinity of the MOFs. Since the direct introduction of the corresponding groups by means of pre-synthetic approaches is hardly possible, these new PSMs are useful tools for the functionalization of porous solids towards applications such as selective adsorption, separation, and catalysis.

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Section: Resultsmentioning

confidence: 99%

Functionalization of Metal–Organic Frameworks through the Postsynthetic Transformation of Olefin Side Groups

Hindelang

Kronast

Vagin

et al. 2013

Chemistry A European J

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“…Microwave‐assisted solvothermal syntheses have been successfully applied to different types of MOFs. This process, involving heating with microwaves for a short period, affords nanosized crystals . Sometimes also the addition of HCl to the reaction mixture seems to increase porosity and decrease the reaction time …”

Section: Synthesis Of Mofsmentioning

confidence: 99%

“…This process, involving heating with microwaves for a short period, affords nanosized crystals. 64,65 Sometimes also the addition of HCl to the reaction mixture seems to increase porosity and decrease the reaction time. 66 Among the recent methods developed for MOF production are electrochemical techniques characterized by several advantages such as mild synthesis conditions and short reaction times.…”

Section: Synthesis Of Mofsmentioning

confidence: 99%

Application of metal − organic frameworks

Pettinari

Marchetti

Mosca

et al. 2017

Polymer International

188

106

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The burgeoning field of metal − organic frameworks or porous coordination polymers has received increasing interest in recent years. In the last decade these microporous materials have found several applications including storage and separation of gases, sensors, catalysis and functional materials. In order to better design new metal − organic frameworks and porous coordination polymers with specific functionalities a fundamental issue is to achieve a basic understanding of the relationship between molecular parameters and structures, preferred adsorption sites and properties by using using modern theoretical methods. The focus of this mini-review is a description of the potential and emerging applications of metal − organic frameworks.

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“…[6][7][8][9] The synthesis of 9-triptycylamine has been reported [10][11][12][13] and a variety of its derivatives have been intensively investigated. [14][15][16][17][18][19] The synthesis of (9-triptycyl)carboxylic acid [20][21][22] has also been reported, and recently the zinc complex of triptycene-9,10-dicarboxylic acid [23][24][25] has been applied in the preparation of metal-organic frameworks (MOFs). To the best of our knowledge, however, the synthesis of (10-amino-9-triptycyl)carboxylic acid has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of 9-Triptycylisothiocyanate, (10-Amino-9-triptycyl)carboxylic Acid, and Their Derivatives

Xu¹,

Huang²

2014

Synthetic Communications

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In the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU), 9-triptycylisothiocyanate has been synthesized in 91% yield from carbon disulfide and sterically hindered 9-triptycylamine at room temperature. 9-Triptycylisothiocyanate can be further converted to 1-benzyl-3-(9-triptycyl)thiourea. (10-Amino-9-triptycyl)carboxylic acid has also been successfully synthesized via a three-step route starting from methyl 10-nitroanthracene-9-carboylate. Its amino and carboxylic groups can undergo acetylation and amidation, respectively.

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Tandem post-synthetic modification for functionalized metal–organic frameworks via epoxidation and subsequent epoxide ring-opening

Cited by 32 publications

References 17 publications

Functionalization of Metal–Organic Frameworks through the Postsynthetic Transformation of Olefin Side Groups

Functionalization of Metal–Organic Frameworks through the Postsynthetic Transformation of Olefin Side Groups

Application of metal − organic frameworks

Syntheses of 9-Triptycylisothiocyanate, (10-Amino-9-triptycyl)carboxylic Acid, and Their Derivatives

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