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http://hdl.handle.net/10261/11501
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Quesada, Ernesto | - |
dc.contributor.author | Delgado, Javier | - |
dc.contributor.author | Hornillos, Valentín | - |
dc.contributor.author | Acuña, A. Ulises | - |
dc.contributor.author | Amat-Guerri, Francisco | - |
dc.date.accessioned | 2009-03-12T08:34:02Z | - |
dc.date.available | 2009-03-12T08:34:02Z | - |
dc.date.issued | 2007-03-20 | - |
dc.identifier.citation | European Journal of Organic Chemistry 14: 2285-2295 (2007) | en_US |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | http://hdl.handle.net/10261/11501 | - |
dc.description.abstract | Lipophilic fluorescent groups with a chain-like linear conformation emitting in the visible range and with high photostability are presently unavailable. These structures would be of great interest as labels for long-chain fatty acids and phospholipids lacking intrinsic fluorescent groups. With this aim in mind, we report the synthesis and the spectroscopic characterization of a series of emitting amphiphilic lipids that may approach that ideal fluorescent tag. Each lipid was constructed by attaching a linear, all-(E) conjugated pentaene, tetraenyne, -phenyltetraene, or -phenyltrienyne chromophore to a hydrophilic head-group through a polymethylene chain spacer. The key steps of the synthesis were the Pd0-mediated cross-coupling reaction between bromopolyenes and terminal acetylenic compounds, yielding tetraenynes or -phenyltrienynes, and the subsequent triple-bond partial reduction, producing the corresponding pentaenes or -phenyltetraenes in good overall yields. This method represents a further successful example of the so-called acetylenic approach to the indirect high-yield synthesis of polyene systems. In the case of -phenyltrienynes, a higher proportion of the all-(E) isomer was obtained using an alternative method based on the reaction of an -phenyldienylphosphonate with an -acetylenic aldehyde. Some of the resulting compounds exhibit spectral and photochemical properties that warrant their use as emitting lipophilic tags. Thus, the -phenyltetraene and -phenyltrienyne members of the series show intense absorption bands in the 320-370 nm range with fluorescence emission centered at 475 nm and quantum yields up to 0.25. These parameters are appropriate for the applications noted above. | en_US |
dc.description.sponsorship | This work was supported by the Spanish Ministerio de Educación y Ciencia (MEC) (Projects BQU2000-1500 and BQU2003/04413). E. Q., J. D. and V. H. acknowledge predoctoral grants from the same source. | en_US |
dc.format.extent | 4085 bytes | - |
dc.format.mimetype | image/gif | - |
dc.language.iso | eng | en_US |
dc.publisher | John Wiley & Sons | en_US |
dc.rights | closedAccess | en_US |
dc.subject | Amphiphiles | en_US |
dc.subject | Polyenes | en_US |
dc.subject | Cross-coupling | en_US |
dc.subject | Enynes | en_US |
dc.subject | Fluorescent probes | en_US |
dc.title | Synthesis and Spectral Properties of Amphiphilic Lipids with Linear Conjugated Polyene and Phenylpolyene Fluorescent Groups | en_US |
dc.type | artículo | en_US |
dc.identifier.doi | 10.1002/ejoc.200600954 | - |
dc.description.peerreviewed | Peer reviewed | en_US |
dc.relation.publisherversion | http://dx.doi.org/10.1002/ejoc.200600954 | en_US |
dc.identifier.e-issn | 099-0690 | - |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairetype | artículo | - |
item.grantfulltext | none | - |
item.cerifentitytype | Publications | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | No Fulltext | - |
item.languageiso639-1 | en | - |
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