dc.contributor.authorZhao, Yan-Li
dc.contributor.authorLiu, Lihua
dc.contributor.authorZhang, Wenyu
dc.contributor.authorSue, Chi-Hau
dc.contributor.authorLi, Qiaowei
dc.contributor.authorMiljanić, Ognjen Š.
dc.contributor.authorYaghi, Omar M.
dc.contributor.authorStoddart, J. Fraser
dc.date.accessioned2014-10-07T01:25:22Z
dc.date.available2014-10-07T01:25:22Z
dc.date.copyright2009en_US
dc.date.issued2009
dc.identifier.citationZhao, Y. L., Liu, L., Zhang, W., Sue, C. H., Li, Q., Miljanić, O., Yaghi, O.,& Stoddart, J. (2009). Rigid-strut-containing crown ethers and [2]catenanes for incorporation into metal-organic frameworks. Chemistry - a European journal, 15(48), 13356-13380.en_US
dc.identifier.issn0947-6539en_US
dc.identifier.urihttp://hdl.handle.net/10220/23961
dc.description.abstractTo introduce crown ethers into the struts of metal–organic frameworks (MOFs), general approaches have been developed for the syntheses of dicarboxylic acid dibenzo[30]crown-10 (DB30C10DA), dicarboxylic acid di-2,3-naphtho[30]crown-10 (DN30C10DA), dicarboxylic acid bisparaphenylene[34]crown-10 (BPP34C10DA), and dicarboxylic acid 1,5-naphthoparaphenylene[36]crown-10 (NPP36C10DA). These novel crown ethers not only retain the characteristics of their parent crown ethers since they can 1) bind cationic guests and 2) serve as templates for making mechanically interlocked molecules (MIMs), such as catenanes and rotaxanes, but they also present coordination sites to connect with secondary building units (SBUs) in MOFs. The binding behavior of BPP34C10DA with 1,1′-dimethyl-4,4′-bipyridinium bis(hexafluorophosphate) (DMBP⋅2 PF6) has been investigated by means of UV/Vis, fluorescence, and NMR spectroscopic techniques. The crystal superstructure of the complex DMBP⋅2 PF6⊂ BPP34C10DA was determined by X-ray crystallography. The NPP36C10DA-based [2]catenane (H2NPP36C10DC-CAT⋅4 PF6) and the BPP34C10DA-based [2]catenane (H2BPP34C10DC-CAT⋅4 PF6) were prepared in DMF at room temperature by the template-directed clipping reactions of the planarly chiral NPP36C10DA and BPP34C10DA with 1,1′-[1,4-phenylenebis(methylene)]di-4,4′-bipyridin-1-ium bis(hexafluorophosphate) and 1,4-bis(bromomethyl)benzene, respectively. The crystal structure of the dimethyl ester (BPP34C10DE-CAT⋅4 PF6) of the [2]catenane H2BPP34C10DC-CAT⋅4 PF6 was investigated by X-ray crystallography, which revealed racemic R and S isomers with planar chirality present in the crystal in a 1:1 ratio. These crown ether based struts serve as excellent organic ligands to bind with transition metal ions in the construction of MOFs: the crown ethers BPP34C10DA and NPP36C10DA in the presence of Zn(NO3)2⋅4 H2O afforded the MOF-1001 and MOF-1002 frameworks, respectively. The crystal structures of MOF-1001 and MOF-1002 are both cubic and display Fmequation imagem symmetry. The unit cell parameter of the metal–organic frameworks is a=52.9345 Å. Since such MOFs, containing electron-donating crown ethers are capable of docking incoming electron-accepting substrates in a stereoelectronically controlled fashion, the present work opens a new access to the preparation and application of MOFs.en_US
dc.language.isoenen_US
dc.relation.ispartofseriesChemistry - a European journalen_US
dc.rights© 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheimen_US
dc.subjectDRNTU::Science::Physics::Atomic physics::Properties of matter and antimatter
dc.titleRigid-strut-containing crown ethers and [2]catenanes for incorporation into metal-organic frameworksen_US
dc.typeJournal Article
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doihttp://dx.doi.org/10.1002/chem.200902350
dc.identifier.rims159762


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