File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: ExBox: A polycyclic aromatic hydrocarbon scavenger

TitleExBox: A polycyclic aromatic hydrocarbon scavenger
Authors
Issue Date2013
Citation
Journal of the American Chemical Society, 2013, v. 135, n. 1, p. 183-192 How to Cite?
AbstractA template-directed protocol, which capitalizes on donor-acceptor interactions, is employed to synthesize a semi-rigid cyclophane (ExBox 4+) that adopts a box-like geometry and is comprised of π-electron-poor 1,4-phenylene-bridged ("extended") bipyridinium units (ExBIPY2+). ExBox4+ functions as a high-affinity scavenger of an array of different polycyclic aromatic hydrocarbons (PAHs), ranging from two to seven fused rings, as a result of its large, accommodating cavity (approximately 3.5 Å in width and 11.2 Å in length when considering the van der Waals radii) and its ability to form strong non-covalent bonding interactions with π-electron-rich PAHs in either organic or aqueous media. In all, 11 PAH guests were observed to form inclusion complexes with ExBox4+, with coronene being the largest included guest. Single-crystal X-ray diffraction data for the 11 inclusion complexes ExBox 4+⊂PAH as well as UV/vis spectroscopic data for 10 of the complexes provide evidence of the promiscuity of ExBox4+ for the various PAHs. Nuclear magnetic resonance spectroscopy and isothermal titration calorimetric analyses of 10 of the inclusion complexes are employed to further characterize the host-guest interactions in solution and determine the degree with which ExBox4+ binds each PAH compound. As a proof-of-concept, a batch of crude oil from Saudi Arabia was subjected to extraction with the water-soluble form of the PAH receptor, ExBox·4Cl, resulting in the isolation of different aromatic compounds after ExBox·4Cl was regenerated. © 2012 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/333016
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorBarnes, Jonathan C.-
dc.contributor.authorJuríček, Michal-
dc.contributor.authorStrutt, Nathan L.-
dc.contributor.authorFrasconi, Marco-
dc.contributor.authorSampath, Srinivasan-
dc.contributor.authorGiesener, Marc A.-
dc.contributor.authorMcGrier, Psaras L.-
dc.contributor.authorBruns, Carson J.-
dc.contributor.authorStern, Charlotte L.-
dc.contributor.authorSarjeant, Amy A.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:16:07Z-
dc.date.available2023-10-06T05:16:07Z-
dc.date.issued2013-
dc.identifier.citationJournal of the American Chemical Society, 2013, v. 135, n. 1, p. 183-192-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/333016-
dc.description.abstractA template-directed protocol, which capitalizes on donor-acceptor interactions, is employed to synthesize a semi-rigid cyclophane (ExBox 4+) that adopts a box-like geometry and is comprised of π-electron-poor 1,4-phenylene-bridged ("extended") bipyridinium units (ExBIPY2+). ExBox4+ functions as a high-affinity scavenger of an array of different polycyclic aromatic hydrocarbons (PAHs), ranging from two to seven fused rings, as a result of its large, accommodating cavity (approximately 3.5 Å in width and 11.2 Å in length when considering the van der Waals radii) and its ability to form strong non-covalent bonding interactions with π-electron-rich PAHs in either organic or aqueous media. In all, 11 PAH guests were observed to form inclusion complexes with ExBox4+, with coronene being the largest included guest. Single-crystal X-ray diffraction data for the 11 inclusion complexes ExBox 4+⊂PAH as well as UV/vis spectroscopic data for 10 of the complexes provide evidence of the promiscuity of ExBox4+ for the various PAHs. Nuclear magnetic resonance spectroscopy and isothermal titration calorimetric analyses of 10 of the inclusion complexes are employed to further characterize the host-guest interactions in solution and determine the degree with which ExBox4+ binds each PAH compound. As a proof-of-concept, a batch of crude oil from Saudi Arabia was subjected to extraction with the water-soluble form of the PAH receptor, ExBox·4Cl, resulting in the isolation of different aromatic compounds after ExBox·4Cl was regenerated. © 2012 American Chemical Society.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleExBox: A polycyclic aromatic hydrocarbon scavenger-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja307360n-
dc.identifier.pmid22928610-
dc.identifier.scopuseid_2-s2.0-84872112520-
dc.identifier.volume135-
dc.identifier.issue1-
dc.identifier.spage183-
dc.identifier.epage192-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000313143000037-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats