Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

Nicolaas A. Vermeulen; Olga Karagiaridi; Amy A. Sarjeant; Charlotte L. Stern; Joseph T. Hupp; Omar K. Farha; J. Fraser Stoddart

doi:10.1021/ja407333q

Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

Nicolaas A. Vermeulen, Olga Karagiaridi, Amy A. Sarjeant, Charlotte L. Stern, Joseph T. Hupp^*, Omar K. Farha, J. Fraser Stoddart

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

The aromatizing ring-closing metathesis has been shown to take place inside an extended porous framework. Employing a combination of solvent-assisted linker exchange and postsynthesis modification using olefin metathesis, the noninterpenetrated SALEM-14 was formed and converted catalytically into PAH-MOF-1 with polycyclic aromatic hydrocarbon (PAH) pillars. The metal-organic framework in SALEM-14 prevents "intermolecular" olefin metathesis from occurring between the pillars in the presence of the first generation Hoveyda-Grubbs catalyst, while favoring the production of a PAH, which can be released from the framework under acidic conditions in dimethylsulfoxide.

Original language	English (US)
Pages (from-to)	14916-14919
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	40
DOIs	https://doi.org/10.1021/ja407333q
State	Published - Oct 9 2013

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja407333q

Cite this

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title = "Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework",

abstract = "The aromatizing ring-closing metathesis has been shown to take place inside an extended porous framework. Employing a combination of solvent-assisted linker exchange and postsynthesis modification using olefin metathesis, the noninterpenetrated SALEM-14 was formed and converted catalytically into PAH-MOF-1 with polycyclic aromatic hydrocarbon (PAH) pillars. The metal-organic framework in SALEM-14 prevents {"}intermolecular{"} olefin metathesis from occurring between the pillars in the presence of the first generation Hoveyda-Grubbs catalyst, while favoring the production of a PAH, which can be released from the framework under acidic conditions in dimethylsulfoxide.",

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doi = "10.1021/ja407333q",

language = "English (US)",

volume = "135",

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T1 - Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

AU - Vermeulen, Nicolaas A.

AU - Karagiaridi, Olga

AU - Sarjeant, Amy A.

AU - Stern, Charlotte L.

AU - Hupp, Joseph T.

AU - Farha, Omar K.

AU - Stoddart, J. Fraser

PY - 2013/10/9

Y1 - 2013/10/9

N2 - The aromatizing ring-closing metathesis has been shown to take place inside an extended porous framework. Employing a combination of solvent-assisted linker exchange and postsynthesis modification using olefin metathesis, the noninterpenetrated SALEM-14 was formed and converted catalytically into PAH-MOF-1 with polycyclic aromatic hydrocarbon (PAH) pillars. The metal-organic framework in SALEM-14 prevents "intermolecular" olefin metathesis from occurring between the pillars in the presence of the first generation Hoveyda-Grubbs catalyst, while favoring the production of a PAH, which can be released from the framework under acidic conditions in dimethylsulfoxide.

AB - The aromatizing ring-closing metathesis has been shown to take place inside an extended porous framework. Employing a combination of solvent-assisted linker exchange and postsynthesis modification using olefin metathesis, the noninterpenetrated SALEM-14 was formed and converted catalytically into PAH-MOF-1 with polycyclic aromatic hydrocarbon (PAH) pillars. The metal-organic framework in SALEM-14 prevents "intermolecular" olefin metathesis from occurring between the pillars in the presence of the first generation Hoveyda-Grubbs catalyst, while favoring the production of a PAH, which can be released from the framework under acidic conditions in dimethylsulfoxide.

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Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

Abstract

ASJC Scopus subject areas

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CCDC 950458: Experimental Crystal Structure Determination

CCDC 950460: Experimental Crystal Structure Determination

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Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework

Abstract

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Datasets

CCDC 950458: Experimental Crystal Structure Determination

CCDC 950460: Experimental Crystal Structure Determination

Cite this