Publication
2-Hydroxychalcone−β-Cyclodextrin Conjugate with pH-Modulated Photoresponsive Binding Properties
| dc.contributor.author | Paulino, Micael | |
| dc.contributor.author | Pérez-Juste, Ignacio | |
| dc.contributor.author | Cid, María Magdalena | |
| dc.contributor.author | Da Silva, José Paulo | |
| dc.contributor.author | Pereira, M. Manuela A. | |
| dc.contributor.author | Basílio, Nuno | |
| dc.date.accessioned | 2023-01-25T13:53:57Z | |
| dc.date.available | 2023-01-25T13:53:57Z | |
| dc.date.issued | 2022 | |
| dc.description.abstract | Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and synthesis of a pH and light-responsive 2-hydroxychalcone-beta-cyclodextrin conjugate (1-Ct) and its characterization by spectroscopic and computational methods. 1-Ct follows the typical reaction network of trans-chalcone-flavylium photoswitches. Upon light irradiation, 1-Ct can be photochemically converted into the cis-chalcone/hemiketal forms (1-Cc/1-B) under neutral pH conditions or to the flavylium cation (1-AH+) at acidic pH values. This stimuli-responsive beta-cyclodextrin host, 1Ct, was found to form stronger intramolecular self-inclusion complexes (Kintra = 14) than 1-AH+ (Kintra = 3) and weaker than 1-Cc/1-B (overall Kintra = 179), allowing control over their stability and binding properties by combinations of pH and light stimuli. | pt_PT |
| dc.description.sponsorship | ROTEIRO/0031/2013-PINFRA/22161/2016 | |
| dc.description.sponsorship | EMBRC.PT ALG-01-0145-FEDER-022121 | |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.doi | 10.1021/acs.joc.2c01875 | pt_PT |
| dc.identifier.issn | 0022-3263 | |
| dc.identifier.uri | http://hdl.handle.net/10400.1/18926 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | American Chemical Society | pt_PT |
| dc.relation | Associated Laboratory for Green Chemistry - Clean Technologies and Processes | |
| dc.relation | Associated Laboratory for Green Chemistry - Clean Technologies and Processes | |
| dc.relation | Algarve Centre for Marine Sciences | |
| dc.relation | Not Available | |
| dc.title | 2-Hydroxychalcone−β-Cyclodextrin Conjugate with pH-Modulated Photoresponsive Binding Properties | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.awardTitle | Associated Laboratory for Green Chemistry - Clean Technologies and Processes | |
| oaire.awardTitle | Associated Laboratory for Green Chemistry - Clean Technologies and Processes | |
| oaire.awardTitle | Algarve Centre for Marine Sciences | |
| oaire.awardTitle | Not Available | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04326%2F2020/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FQUI-COL%2F32351%2F2017/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00466%2F2017%2FCP1462%2FCT0013/PT | |
| oaire.citation.endPage | 14432 | pt_PT |
| oaire.citation.issue | 21 | pt_PT |
| oaire.citation.startPage | 14422 | pt_PT |
| oaire.citation.title | The Journal of Organic Chemistry | pt_PT |
| oaire.citation.volume | 87 | pt_PT |
| oaire.fundingStream | 6817 - DCRRNI ID | |
| oaire.fundingStream | 6817 - DCRRNI ID | |
| oaire.fundingStream | 6817 - DCRRNI ID | |
| oaire.fundingStream | 9471 - RIDTI | |
| oaire.fundingStream | CEEC IND 2017 | |
| person.familyName | Silva | |
| person.givenName | José Paulo da | |
| person.identifier.ciencia-id | 3413-C4F4-73F7 | |
| person.identifier.orcid | 0000-0002-6458-7328 | |
| person.identifier.rid | A-4606-2008 | |
| person.identifier.scopus-author-id | 7201733236 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| rcaap.rights | restrictedAccess | pt_PT |
| rcaap.type | article | pt_PT |
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