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dc.contributor.author
Thilgen, Carlo
dc.contributor.author
Diederich, François
dc.date.accessioned
2022-08-04T14:00:21Z
dc.date.available
2017-06-10T08:32:31Z
dc.date.available
2022-08-04T14:00:21Z
dc.date.issued
2003
dc.identifier.issn
0151-9093
dc.identifier.issn
2105-2409
dc.identifier.uri
http://hdl.handle.net/20.500.11850/55180
dc.description.abstract
Regio- and stereoselective tether-directed remote functionalization was used to prepare three dimensional building blocks for supramolecular construction and advanced materials. A C60-ionophore conjugate was prepared selectively as trans-1 regioisomer in a K+-templated Bingel addition of a bismalonate derived from dibenzo[18]crown-6. It can act as an ion sensor and the close proximity of complexed potassium ions to the fullerene sphere induces anodical shifts in the redox potentials of the latter. A similar but even more pronounced effect is seen in a C70 cage which is sandwiched between two crown ethers. Favorable C60-porphyrin ground state interactions were detected by steady-state and time-resolved absorption and luminescence spectroscopy of a trans-1 type, doubly bridged dyad as well as in a fullerene connected to two porphyrins by single linkages. In toluene, both the zinc porphyrin- and the fullerene-centered excited states are deactivated to a lower-lying charge-transfer (CT) state which emits in the infrared (IR) spectral region. Enantiopure bis-adducts of C60 with the chiral cis-3 functionalization pattern were prepared by regio- and stereoselective Bingel macrocyclizations using non-racemic chiral tethers. Configurational assignment was possible by a combination of computational and 1H NMR-spectroscopic conformational analysis and it was confirmed by a comparison of its circular dichroism (CD) spectra with the measured and calculated spectra of another C60 adduct with the same π-chromophore. Finally, a polysiloxane-supported fullerene derivative was prepared and proven to act as a heterogeneous sensitizer for the selective photooxidation of sulfides to sulfoxides by 1O2.
en_US
dc.language.iso
en
en_US
dc.publisher
Société Chimique de France
en_US
dc.subject
Fullerenes
en_US
dc.subject
Chirality
en_US
dc.subject
Tether-directed remote functionalization
en_US
dc.subject
Ion sensors
en_US
dc.subject
Fullerene-porphyrin dyads
en_US
dc.subject
Solid-supported photooxidation sensitizer
en_US
dc.title
Vers de nouveaux matériaux basés sur les fullerènes
en_US
dc.title.alternative
On the way to new fullerene-based materials
en_US
dc.type
Journal Article
ethz.journal.title
L’Actualité chimique
ethz.journal.volume
265
en_US
ethz.journal.issue
4-5
en_US
ethz.journal.abbreviated
Actual. Chim.
ethz.pages.start
114
en_US
ethz.pages.end
118
en_US
ethz.identifier.wos
ethz.publication.place
Paris
en_US
ethz.publication.status
published
en_US
ethz.identifier.url
https://new.societechimiquedefrance.fr/numero/vers-de-nouveaux-materiaux-bases-sur-les-fullerenes-p114-n265/
ethz.date.deposited
2017-06-10T08:33:07Z
ethz.source
ECIT
ethz.identifier.importid
imp59364fb84fd2692100
ethz.ecitpid
pub:88863
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2017-07-20T15:22:57Z
ethz.rosetta.lastUpdated
2022-03-28T11:00:03Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
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