Publication:
Mechanically interlocked profragrances for the controlled release of scents

Simple item page
dc.contributor.authorLopez-Sanchez, Jorge
dc.contributor.authorAlajarín, Mateo
dc.contributor.authorPastor, Aurelia
dc.contributor.authorBerna Cánovas, José
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2024-10-02T08:51:31Z
dc.date.available2024-10-02T08:51:31Z
dc.date.issued2021-10-01
dc.description© 2021 The Authors. This manuscript version is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by/4.0/ This document is the Published version of a Published Work that appeared in final form in The Journal of Organic Chemistry. To access the final edited and published work see https://doi.org/10.1021/acs.joc.1c01725
dc.description.abstractThe synthesis of a series of interlocked profragrances and the study of the controlled release of the corresponding scents are reported. The structures of the profragrances are based on a [2]pseudorotaxane scaffold with a fumaramate thread derived from perfumery alcohols and a tetrabenzylamido ring. The delivery of the scents was accomplished by sequential thermal dethreading and further enzymatic hydrolysis. Alternatively, the dethreading can be achieved by increasing the polarity of the solvent or photochemical isomerization. The temperature of dethreading can be modulated by the steric demand of the ends of the thread, which allows the selection of different precursor structures depending on the desired rates of delivery. The inputs and outputs for the controlled release of the interlocked profragrances correspond to those of YES or AND logic gates.es
dc.formatapplication/pdfes
dc.format.extent10es
dc.identifier.citationThe Journal of Organic Chemistry, 2021, Vol. 86, N. 21, pp. 15045–15054
dc.identifier.doihttps://doi.org/10.1021/acs.joc.1c01725
dc.identifier.issnPrint: 0022-3263
dc.identifier.issnElectronic: 1520-6904
dc.identifier.urihttp://hdl.handle.net/10201/144485
dc.languageenges
dc.publisherACS Publicationses
dc.relationThis work was supported by the Spanish Ministry of Science and Innovation (Project CTQ2017-87231-P, financed jointly by FEDER-UE and PID2020-113686GB-I00/AEI/10.13039/501100011033) and the Fundacion Seneca-CARM (Project 20811/PI/18). J.L.-S. also thanks the MICIU for his predoctoral contract (PRE2018-084314, financed together by FSE-UE). The authors also acknowledge the division of Takasago Int. Chemicals Europe in Murcia for providing us the terpenoids shown in Chart 1.es
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.joc.1c01725es
dc.relation.requireshttps://pubs.acs.org/doi/suppl/10.1021/acs.joc.1c01725/suppl_file/jo1c01725_si_001.pdfes
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectRotaxaneses
dc.subjectStimulus-Responsive Systemses
dc.subjectEnzymatic Hydrolysises
dc.subjectProfraganceses
dc.subjectNon-covalent interactionses
dc.subjectPerfumery Alcoholses
dc.subject.otherCDU::5 - Ciencias puras y naturaleses
dc.titleMechanically interlocked profragrances for the controlled release of scentses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
21JOC15045_MIPs.pdf
Size:
2.06 MB
Format:
Adobe Portable Document Format
Description:
Mechanically Interlocked Profragrances
Download
License bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
license.txt
Size:
2.26 KB
Format:
Item-specific license agreed upon to submission
Description:
Download
Collections
Artículos