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

56 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

Access to Document

10.1021/ja407333q

Cite this

@article{9304bfdac3f049ee905868c391b36857,

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.",

author = "Vermeulen, {Nicolaas A.} and Olga Karagiaridi and Sarjeant, {Amy A.} and Stern, {Charlotte L.} and Hupp, {Joseph T.} and Farha, {Omar K.} and Stoddart, {J. Fraser}",

year = "2013",

month = oct,

day = "9",

doi = "10.1021/ja407333q",

language = "English (US)",

volume = "135",

pages = "14916--14919",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "40",

}

Aromatizing olefin metathesis by ligand isolation inside a metal- organic framework. / Vermeulen, Nicolaas A.; Karagiaridi, Olga; Sarjeant, Amy A.; Stern, Charlotte L.; Hupp, Joseph T.; Farha, Omar K.; Stoddart, J. Fraser.

In: Journal of the American Chemical Society, Vol. 135, No. 40, 09.10.2013, p. 14916-14919.

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

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84885586612&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84885586612&partnerID=8YFLogxK

U2 - 10.1021/ja407333q

DO - 10.1021/ja407333q

M3 - Article

C2 - 24047342

AN - SCOPUS:84885586612

VL - 135

SP - 14916

EP - 14919

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 40

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this