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Water-soluble naphthalimide-based 'Pourbaix sensors': pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer

hal.structure.identifierDepartment of Chemistry [Malta]
dc.contributor.authorJOHNSON, Alex D.
hal.structure.identifierDepartment of Chemistry [Malta]
dc.contributor.authorPATERSON, Kyle A.
hal.structure.identifierDepartment of Chemistry [Malta]
dc.contributor.authorSPITERI, Jake C.
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorDENISOV, Sergey A.
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorJONUSAUSKAS, Gediminas
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorTRON, Arnaud
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMCCLENAGHAN, Nathan D.
hal.structure.identifierDepartment of Chemistry [Malta]
dc.contributor.authorMAGRI, David C.
dc.date.created2016-06-28
dc.date.issued2016-12-01
dc.identifier.issn1144-0546
dc.description.abstractEnTwo novel naphthalimide-based 'Pourbaix sensors' for redox potential and pH were designed based on a 'fluorophore–spacer 1 –receptor–spacer 2 –electron-donor' configuration. The synthesised molecular logic gates consist of an alkylated 1,8-naphthalimide fluorophore connected to a tertiary amine by a flexible ethylene spacer to a ferrocene moiety via a methylene spacer. The UV-visible absorption and steady state fluorescent properties were examined in methanol and 1 : 1 (v/v) methanol/water. The spectroscopic properties are modulated by internal charge transfer (ICT) and photoinduced electron transfer (PET) mechanisms. A log b H + of 9.2 and 8.7 were determined in 1 : 1 (v/v) methanol/water for the methylated 1 and butylated 2 compounds, respectively. An apparent log b Fe 3+ of 4.2 was determined in 1 : 1 (v/v) methanol/ water at pH 4. Time-resolved spectroscopic studies elucidated the stimulus-modulated photoinduced electron transfer pathways. In the oxidised and protonated state, 1 exhibits a single fluorescence lifetime of 8.5 ns, while an efficient photoinduced electron transfer characterised by a time constant of 20 ps is revealed by femtosecond transient absorption spectroscopy in the absence of a perturbing stimulus.
dc.description.sponsorshipArchitectures à base de foldamères pour le transport d'electrons - ANR-12-BS08-0007
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.rights.urihttp://creativecommons.org/licenses/by-sa/
dc.title.enWater-soluble naphthalimide-based 'Pourbaix sensors': pH and redox-activated fluorescent AND logic gates based on photoinduced electron transfer
dc.typeArticle de revue
dc.identifier.doi10.1039/C6NJ02023B
dc.subject.halPhysique [physics]/Physique [physics]/Chimie-Physique [physics.chem-ph]
bordeaux.journalNew Journal of Chemistry
bordeaux.page9917 - 9922
bordeaux.volume40
bordeaux.issue12
bordeaux.peerReviewedoui
hal.identifierhal-01426556
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01426556v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=New%20Journal%20of%20Chemistry&rft.date=2016-12-01&rft.volume=40&rft.issue=12&rft.spage=9917%20-%209922&rft.epage=9917%20-%209922&rft.eissn=1144-0546&rft.issn=1144-0546&rft.au=JOHNSON,%20Alex%20D.&PATERSON,%20Kyle%20A.&SPITERI,%20Jake%20C.&DENISOV,%20Sergey%20A.&JONUSAUSKAS,%20Gediminas&rft.genre=article


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