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Development of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and π-Conjugated Groups

hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPEYRARD, Lisa
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorDUMARTIN, Marie-Laurence
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorCHIERICI, Sabine
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPINET, Sandra
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorJONUSAUSKAS, Gediminas
hal.structure.identifierInstitut des Maladies Neurodégénératives [Bordeaux] [IMN]
dc.contributor.authorMEYRAND, Pierre
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorGOSSE, Isabelle
dc.date.created2012-06-19
dc.date.issued2012-06-30
dc.identifier.issn0022-3263
dc.description.abstractEnCyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or π-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C3-triiodocyclotriveratrylene (CTV-I3), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with π-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I3 to introduce novel functionalities into CTVs to keep exploring their potential applications. Cyclotriveratrylene analogues (CTVs) are supramolecular bowl-shaped molecules known for their ability to complex organic and organometallic guests, to form liquid crystals, polymers, or nanostructures. In this Article, we report the synthesis of new cyclotriveratrylene analogues with fluorescence properties in which various electron-withdrawing or π-extended conjugated groups are appended to the wide rim ortho to the methoxy-donating groups. Synthetically, these functionalized CTVs cannot be obtained as CTVs with electron-rich functions by the typical method (i.e., the trimerization of the corresponding benzyl alcohol) but are prepared from a common key intermediate, the C3-triiodocyclotriveratrylene (CTV-I3), in good yields. Despite the synthetic difficulties encountered due to the presence of three reactive centers, we have demonstrated the possibility of performing Sonogashira coupling and Huisgen cycloaddition reactions directly to the CTV core for the first time. CTVs with π-extended conjugated groups reveal interesting fluorescence profiles. More broadly, this study utilizes CTV-I3 to introduce novel functionalities into CTVs to keep exploring their potential applications.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.title.enDevelopment of Functionalized Cyclotriveratrylene Analogues: Introduction of Withdrawing and π-Conjugated Groups
dc.typeArticle de revue
dc.identifier.doi10.1021/jo301183b
dc.subject.halPhysique [physics]/Physique [physics]/Chimie-Physique [physics.chem-ph]
bordeaux.journalJournal of Organic Chemistry
bordeaux.page7023-7027
bordeaux.volume77
bordeaux.issue16
bordeaux.peerReviewedoui
hal.identifierhal-00731287
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00731287v1
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