DC Field | Value | Language |
---|---|---|
dc.contributor.author | Jung, JH | ko |
dc.contributor.author | Do, Youngkyu | ko |
dc.contributor.author | Lee, YA | ko |
dc.contributor.author | Shimizu, T | ko |
dc.date.accessioned | 2013-03-07T17:35:44Z | - |
dc.date.available | 2013-03-07T17:35:44Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2005-09 | - |
dc.identifier.citation | CHEMISTRY-A EUROPEAN JOURNAL, v.11, no.19, pp.5538 - 5544 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10203/90797 | - |
dc.description.abstract | Nine phenyl glucoside or galactoside amphiphiles possessing a saturated or unsaturated long alkyl-chain group as the self-assembling unit of a highly organized, molecular architecture were synthesized. Their self-assembly properties were investigated by using energy-filtering TEM (EF-TEM), SEM, CD, XRD, and FT-IR techniques. Compound 2, possessing one cis double bond in the lipophilic portion, exhibited twisted helical fibers, which formed a bilayered structure with a 3.59 nm period, while 3 exhibited helical ribbons and left-handed nanotubular structures with 150-200 nm inner diameters and a wall thickness of approximately 20 nm. Very interestingly, 4, possessing three cis double bonds, exhibited a nanotubular structure with an inner diameter of approximately 70 nm and a d spacing value of 4.62 nm. On the other hand, 7, possessing two trans double bonds in the lipophilic region, exhibited crystal- or plate-like structures, which formed a bilayer structure with a d spacing value of 3.93 nm. These results indicate that the self-assembly properties are strongly dependent on the type of double bond. Furthermore, 8 and 9, with the galactopyranose moiety, revealed helical ribbon and well-defined double helical fiber structures, respectively. These findings support the view that the orientation of the intermolecular hydrogen-bonding interaction between the sugar moieties plays a critical role in producing the nanotubular structures. According to CD and powder XRD experiments, the relatively strong intermolecular hydrogen-bonding interaction of the glucopyranoside moiety in 3 and 4 provided a highly ordered chiral packing structure. Even though these compounds formed a weak hydrophobic interaction between lipophilic groups, it led to the formation of the nanotubular structure. | - |
dc.language | English | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject | AXIAL-RATIO NANOSTRUCTURES | - |
dc.subject | CHIRAL LIPID TUBULES | - |
dc.subject | SEMIFLUORINATED ALKANES | - |
dc.subject | CHROMATIC TRANSITION | - |
dc.subject | GELATION ABILITY | - |
dc.subject | HELICAL RIBBONS | - |
dc.subject | NANOFIBERS | - |
dc.subject | NANOTUBES | - |
dc.subject | MORPHOLOGY | - |
dc.subject | BILAYER | - |
dc.title | Self-assembling structures of long-chain sugar-based amphiphiles influenced by the introduction of double bonds | - |
dc.type | Article | - |
dc.identifier.wosid | 000232081900006 | - |
dc.identifier.scopusid | 2-s2.0-25444465936 | - |
dc.type.rims | ART | - |
dc.citation.volume | 11 | - |
dc.citation.issue | 19 | - |
dc.citation.beginningpage | 5538 | - |
dc.citation.endingpage | 5544 | - |
dc.citation.publicationname | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.identifier.doi | 10.1002/chem.200401288 | - |
dc.contributor.localauthor | Do, Youngkyu | - |
dc.contributor.nonIdAuthor | Jung, JH | - |
dc.contributor.nonIdAuthor | Lee, YA | - |
dc.contributor.nonIdAuthor | Shimizu, T | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | amphiphiles | - |
dc.subject.keywordAuthor | carbohydrates | - |
dc.subject.keywordAuthor | lipids | - |
dc.subject.keywordAuthor | nanotubes | - |
dc.subject.keywordAuthor | self-assembly | - |
dc.subject.keywordPlus | AXIAL-RATIO NANOSTRUCTURES | - |
dc.subject.keywordPlus | CHIRAL LIPID TUBULES | - |
dc.subject.keywordPlus | SEMIFLUORINATED ALKANES | - |
dc.subject.keywordPlus | CHROMATIC TRANSITION | - |
dc.subject.keywordPlus | GELATION ABILITY | - |
dc.subject.keywordPlus | HELICAL RIBBONS | - |
dc.subject.keywordPlus | NANOFIBERS | - |
dc.subject.keywordPlus | NANOTUBES | - |
dc.subject.keywordPlus | MORPHOLOGY | - |
dc.subject.keywordPlus | BILAYER | - |
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