Publication: Mechanically interlocked profragrances for the controlled release of scents
Authors
Lopez-Sanchez, Jorge ; Alajarín, Mateo ; Pastor, Aurelia ; Berna Cánovas, José
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Publisher
ACS Publications
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DOI
https://doi.org/10.1021/acs.joc.1c01725
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info:eu-repo/semantics/article
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
Abstract
The 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.
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Citation
The Journal of Organic Chemistry, 2021, Vol. 86, N. 21, pp. 15045–15054
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Este ítem está sujeto a una licencia Creative Commons. http://creativecommons.org/licenses/by/4.0/