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A supramolecular approach towards the photorelease of encapsulated caged acids in water: 7-diethylaminothio-4-coumarinyl molecules as triggers

2024-11Journal article Restricted access
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dc.contributor.authorGhosh, Sujit Kumar
dc.contributor.authorChatterjee, Shreya
dc.contributor.authorBoruah, Paras Pratim
dc.contributor.authorMandal, Satyajit
dc.contributor.authorSilva, José Paulo da
dc.contributor.authorSrinivasan, Varadharajan
dc.contributor.authorRamamurthy, Vaidhyanathan
dc.date.accessioned2024-11-27T14:00:01Z
dc.date.available2024-11-27T14:00:01Z
dc.date.issued2024-11
dc.description.abstractHerein, we establish the release of aliphatic acids in water upon excitation of 7-diethylaminothio-4-coumarinyl derivatives encapsulated within the organic host octa acid (OA). The 7-diethylaminothio-4-coumarinyl skeleton, employed here as the trigger, photoreleases caged molecules from the excited triplet state, in contrast to its carbonyl analogue, where the same reaction is known to occur from the excited singlet state. Encapsulation in OA solubilizes molecules in water that are otherwise water-insoluble, and retains the used trigger within itself following the release of the aliphatic acid. Such supramolecular characteristics usher in new features to the photorelease methodology. The thiocarbonyl chromophore extends the absorption of coumarinyl trigger to visible range while enhancing the intersystem crossing (ISC) to the triplet state, making it the reactive state. Despite the non-polar environment within the OA capsules the photocleavage occurs in a heterolytic fashion to release the conjugate base and the used trigger as triplet carbocation in an adiabatic process. Interestingly, the triplet carbocation crosses to the ground singlet surface (closed shell singlet carbocation) with the help of water molecules, possibly aided by C = S chromophore. Utilizing the known excited state dynamics of related thiocoumarinyl and coumarinyl systems, we have identified a few of the important mechanistic features of the photorelease process of 7-diethylaminothio-4-coumarinyl derivatives. Ultrafast excited state dynamic studies and quantum chemical calculations planned should help us better understand the photorelease process so as to effectively exploit the proposed system for potential applications.eng
dc.description.sponsorshipCHE-2204046; EMBRC.PT ALG-01-0145-FEDER-022121
dc.identifier.doi10.1007/s43630-024-00651-1
dc.identifier.eissn1474-9092
dc.identifier.issn1474-905X
dc.identifier.urihttp://hdl.handle.net/10400.1/26353
dc.language.isoeng
dc.peerreviewedyes
dc.publisherSpringer
dc.relationAlgarve Centre for Marine Sciences
dc.relationAlgarve Centre for Marine Sciences
dc.relationCentre for Marine and Environmental Research
dc.relation.ispartofPhotochemical & Photobiological Sciences
dc.rights.uriN/A
dc.subjectSupramolecular photochemistry
dc.subjectOcta acid capsule
dc.subjectTriplet chemistry
dc.subjectPhototriggers
dc.subjectPhotorelease
dc.subjectPhotoprotecting group
dc.subjectThiocoumarins
dc.subjectbeta-Cleavage
dc.subjectNon-Kekule structures
dc.titleA supramolecular approach towards the photorelease of encapsulated caged acids in water: 7-diethylaminothio-4-coumarinyl molecules as triggerseng
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleAlgarve Centre for Marine Sciences
oaire.awardTitleCentre for Marine and Environmental Research
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04326%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04326%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0101%2F2020/PT
oaire.citation.endPage2073
oaire.citation.issue11
oaire.citation.startPage2057
oaire.citation.titlePhotochemical & Photobiological Sciences
oaire.citation.volume23
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameSilva
person.givenNameJosé Paulo da
person.identifier.ciencia-id3413-C4F4-73F7
person.identifier.orcid0000-0002-6458-7328
person.identifier.ridA-4606-2008
person.identifier.scopus-author-id7201733236
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
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