Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles

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dc.contributor.author Helttunen, Kaisa
dc.contributor.author Salorinne, Kirsi
dc.contributor.author Barboza, Tahnie
dc.contributor.author Barbosa, Hélène Campos
dc.contributor.author Suhonen, Aku
dc.contributor.author Nissinen, Maija
dc.date.accessioned 2012-06-05T07:59:16Z
dc.date.available 2013-06-01T21:45:03Z
dc.date.issued 2012
dc.identifier.citation Helttunen, K., Salorinne, K., Barboza, T., Barbosa, H., Suhonen, A., & Nissinen, M. (2012). Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles. New Journal of Chemistry, 36 (3), 789-795. doi:10.1039/C2NJ20981K Retrieved from http://pubs.rsc.org/en/content/articlelanding/2012/nj/c2nj20981k fi
dc.identifier.issn 1144-0546
dc.identifier.other TUTKAID_51198
dc.identifier.uri http://hdl.handle.net/123456789/37966
dc.description.abstract A group of seven resorcinarene bis-crown ethers (CNBC5) with two polyether bridges at the upper rim and either propyl, butyl, pentyl, heptyl, nonyl, decyl or undecyl groups at the lower rim were synthesized and their binding properties with Cs+ were investigated by NMR titration. The bis-crowns form 1:2 complexes with Cs+ with binding constants of logK 4–5. Crystal structures of bis-crowns and their Cs+ and K+ complexes were studied and different packing motifs were found depending on the alkyl chain length. Short ethyl, propyl and butyl alkyl chains gave a layer or pillar packing where the polar and non-polar regions cannot be distinguished, whereas longer pentyl and decyl chains formed bilayers. Amphiphilic properties and self-assembly in water were studied by preparing solid lipid nanoparticles (SLNs) from the bis-crowns. All investigated compounds formed stable SLNs showing amphiphilic character, which in the case of the short chain bis-crowns probably arises from their locked boat conformation separating the polar face of the molecule from the non-polar face.
dc.language.iso eng
dc.publisher Centre National de la Recherche Scientifique and The Royal Society of Chemistry
dc.relation.ispartof New Journal of Chemistry
dc.relation.uri http://pubs.rsc.org/en/content/articlelanding/2012/nj/c2nj20981k
dc.rights © Royal Society of Chemistry. This is an electronic final draft version of an article whose final and definitive form has been published in the journal 'New Journal of Chemistry' by RSC.
dc.subject.other supramolekyylikemia fi
dc.subject.other resorsinareeni fi
dc.subject.other kaliksareeni fi
dc.subject.other makrosyklinen yhdiste fi
dc.subject.other cesium fi
dc.subject.other kalium fi
dc.subject.other kompleksi fi
dc.subject.other kiinteä lipidipartikkeli fi
dc.subject.other röntgenkristallografia fi
dc.subject.other itsejärjestäytyminen fi
dc.subject.other amfifiili fi
dc.subject.other ydinmagneettinen resonanssi fi
dc.subject.other supramolecular chemistry fi
dc.subject.other resorcinarene fi
dc.subject.other calixarene fi
dc.subject.other macrocyclic compound fi
dc.subject.other caesium fi
dc.subject.other potassium fi
dc.subject.other complex fi
dc.subject.other solid lipid nanoparticle fi
dc.subject.other X-ray crystallography fi
dc.subject.other self-assembly fi
dc.subject.other amphiphile fi
dc.subject.other nuclear magnetic resonance fi
dc.title Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles
dc.type Article en
dc.identifier.urn URN:NBN:fi:jyu-201205311768
dc.subject.kota 116
dc.contributor.laitos Kemian laitos fi
dc.contributor.laitos Department of Chemistry en
dc.contributor.oppiaine orgaaninen kemia fi
jyx.tutka.volyme 36
jyx.tutka.mnumber 3
jyx.tutka.pagetopage 789-795
dc.type.uri http://purl.org/eprint/type/SubmittedJournalArticle
dc.identifier.doi 10.1039/C2NJ20981K
dc.date.updated 2012-05-31T03:30:05Z
eprint.status http://purl.org/eprint/type/status/PeerReviewed

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