Postsynthetic Modification of Metal-Organic Frameworks through Nitrile Oxide-Alkyne Cycloaddition

Inorganic Chemistry
Tobias von ZonsAdelheid Godt

Abstract

Postsynthetic modification of metal-organic frameworks is an important method to tailor their properties. We report on the nitrile oxide-alkyne cycloaddition (NOAC) as a modification tool, a reaction requiring neither strained alkynes nor a catalyst. This is demonstrated with the reaction of nitrile oxides with PEPEP-PIZOF-15 and -19 at room temperature. PIZOF-15 and -19 are porous Zr-based MOFs (BET surface areas 1740 and 960 m2g-1, respectively) consisting of two mutually interpenetrating UiO-type frameworks with linkers of the type-O2C[PE-P(R1,R2)-EP]CO2-(P, phenylene; E, ethynylene; R1and R2, side chains at the central benzene ring with R1= R2= OCH2C≡CH or R1= OCH2C≡CH and R2= O(CH2CH2O)3Me). Their syntheses, using benzoic acid as a modulator, and their characterization are reported herein. The propargyloxy (OCH2C≡CH) side chains contain the ethyne moieties needed for NOAC. Formation of nitrile oxides through oxidation of oximes in aqueous ethanolic solution in the presence of PEPEP-PIZOF-15 and -19 resulted in the reaction of 96-100% of the ethyne moieties to give isoxazoles. Thereby the framework was preserved. The type of nitrile oxide RCNO was greatly varied with R being isopentyl, tolyl, 2-pyridyl, and pentafluoropheny...Continue Reading

References

Sep 27, 2008·Journal of the American Chemical Society·Jasmina Hafizovic CavkaKarl Petter Lillerud
Oct 9, 2008·Journal of the American Chemical Society·Yuta GotoKazuki Sada
Jun 19, 2009·Journal of the American Chemical Society·Christian J DoonanOmar M Yaghi
Jul 10, 2009·Chemical Communications : Chem Comm·Ishwar SinghFrances Heaney
Sep 3, 2009·Angewandte Chemie·Kristine K Tanabe, Seth M Cohen
Sep 10, 2009·Journal of the American Chemical Society·Tendai GadzikwaSonBinh T Nguyen
Jan 13, 2010·Organic & Biomolecular Chemistry·Virginie AlgayFrances Heaney
Mar 18, 2010·Journal of the American Chemical Society·Marie SavonnetDavid Farrusseng
Mar 24, 2010·Chemical Society Reviews·Patricia L Golas, Krzysztof Matyjaszewski
May 12, 2010·Chemistry : a European Journal·Katrin GutsmiedlThomas Carell
Jun 23, 2010·Inorganic Chemistry·Kristine K Tanabe, Seth M Cohen
Aug 4, 2010·Organic Letters·Tohru MatsumuraToshikazu Takata
Nov 26, 2010·Chemical Society Reviews·Kristine K Tanabe, Seth M Cohen
Dec 25, 2010·Journal of the American Chemical Society·Brian C SandersGeert-Jan Boons
Feb 3, 2011·Chemical Communications : Chem Comm·Anup M JawalekarFloris L van Delft
Apr 18, 2012·Chemistry : a European Journal·Pascal RoyAdelheid Godt
Apr 26, 2012·Chemical Communications : Chem Comm·Boris D ZlatopolskiyBernd Neumaier
Nov 2, 2012·Journal of the American Chemical Society·Chong LiuNathaniel L Rosi
Mar 28, 2013·Chemical Reviews·Prakasam ThirumuruganKrzysztof Jozwiak
Jul 24, 2013·Chemical Communications : Chem Comm·Chen-Gang WangToshikazu Takata
Nov 29, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Zhengbang WangChristof Wöll
Apr 15, 2015·Accounts of Chemical Research·Guillaume DelaittreChristopher Barner-Kowollik
Sep 5, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Meike A GotthardtWolfgang Kleist
Feb 11, 2016·Journal of the American Chemical Society·Juncong JiangOmar M Yaghi
Feb 24, 2016·The Journal of Organic Chemistry·Mian QiAdelheid Godt
Aug 31, 2016·Topics in Current Chemistry·Maiyun YangPeng R Chen
Aug 31, 2016·Topics in Current Chemistry·Thomas Carell, Milan Vrabel
Sep 9, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alessandro Mandoli
Oct 28, 2016·Bioconjugate Chemistry·Jan-Philip MeyerBrian M Zeglis
Jan 25, 2017·Journal of the American Chemical Society·Seth M Cohen
Jun 2, 2017·Chemical Science·Assunta MarrocchiLuigi Vaccaro
Oct 6, 2017·Chemical Communications : Chem Comm·Sana NayabBasit Yameen

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Citations

Jul 4, 2018·Chemistry : a European Journal·Alexander MohmeyerPeter Behrens

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