dc.creator | Rivero Barbarroja, Gonzalo | es |
dc.creator | Fernández Clavero, C. | es |
dc.creator | García Iriepa, C. | es |
dc.creator | Marcelo, G. | es |
dc.creator | Padilla Pérez, María del Carmen | es |
dc.creator | Neva, T. | es |
dc.creator | Benito, J. M. | es |
dc.creator | Maisonneuve, S. | es |
dc.creator | Ortiz Mellet, Carmen | es |
dc.creator | Xie, J. | es |
dc.creator | García Fernández, J. M. | es |
dc.creator | Mendicuti, F. | es |
dc.date.accessioned | 2023-11-02T15:56:06Z | |
dc.date.available | 2023-11-02T15:56:06Z | |
dc.date.issued | 2023 | |
dc.identifier.citation | Rivero Barbarroja, G., Fernández Clavero, C., García Iriepa, C., Marcelo, G., Padilla Pérez, M.d.C., Neva, T.,...,Mendicuti, F. (2023). Reversible Light-Induced Dimerization of Secondary Face Azobenzene-Functionalized β-Cyclodextrin Derivatives. Journal of Organic Chemistry, 88 (13), 8674-8689. https://doi.org/10.1021/acs.joc.3c00564. | |
dc.identifier.issn | 0022-3263 | es |
dc.identifier.issn | 1520-6904 | es |
dc.identifier.uri | https://hdl.handle.net/11441/150060 | |
dc.description.abstract | β-cyclodextrin (βCyD) derivatives equipped with aromatic appendages at the secondary face exhibit tailorable self-assembling capabilities. The aromatic modules can participate in inclusion phenomena and/or aromatic-aromatic interactions. Supramolecular species can thus form that, at their turn, can engage in further co-assembling with third components in a highly regulated manner; the design of nonviral gene delivery systems is an illustrative example. Endowing such systems with stimuli responsiveness while keeping diastereomeric purity and a low synthetic effort is a highly wanted advancement. Here, we show that an azobenzene moiety can be “clicked” to a single secondary O-2 position of βCyD affording 1,2,3-triazole-linked βCyD-azobenzene derivatives that undergo reversible light-controlled self-organization into dimers where the monomer components face their secondary rims. Their photoswitching and supramolecular properties have been thoroughly characterized by UV-vis absorption, induced circular dichroism, nuclear magnetic resonance, and computational techniques. As model processes, the formation of inclusion complexes between a water-soluble triazolylazobenzene derivative and βCyD as well as the assembly of native βCyD/βCyD-azobenzene derivative heterodimers have been investigated in parallel. The stability of the host-guest supramolecules has been challenged against the competitor guest adamantylamine and the decrease of the medium polarity using methanol-water mixtures. The collective data support that the E-configured βCyD-azobenzene derivatives, in aqueous solution, form dimers stabilized by the interplay of aromatic-aromatic and aromatic-βCyD cavity interactions after partial reciprocal inclusion. Photoswitching to the Z-isomer disrupts the dimers into monomeric species, offering opportunity for the spatiotemporal control of the organizational status by light. | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación PID2019-105858RB-I00, PID2020-118403GB-I00, PID2020-118384GB-I00, PID2020-119130GB-I00 | es |
dc.description.sponsorship | Fondo Europeo de Desarrollo Regional PID2021-124247OB-C21 | es |
dc.description.sponsorship | Junta de Andalucía P20_00166, US-1380698, P12-FQM-1467 | es |
dc.description.sponsorship | Universidad de Sevilla FPU18/02922, FPU19/04361 | es |
dc.format | application/pdf | es |
dc.format.extent | 16 p. | es |
dc.language.iso | eng | es |
dc.publisher | American Chemical Society | es |
dc.relation.ispartof | Journal of Organic Chemistry, 88 (13), 8674-8689. | |
dc.rights | Atribución 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.title | Reversible Light-Induced Dimerization of Secondary Face Azobenzene-Functionalized β-Cyclodextrin Derivatives | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/publishedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | PID2019-105858RB-I00 | es |
dc.relation.projectID | PID2020-118403GB-I00 | es |
dc.relation.projectID | PID2020-118384GB-I00 | es |
dc.relation.projectID | PID2020-119130GB-I00 | es |
dc.relation.projectID | PID2021-124247OB-C21 | es |
dc.relation.projectID | P20_00166 | es |
dc.relation.projectID | US-1380698 | es |
dc.relation.projectID | P12-FQM-1467 | es |
dc.relation.projectID | FPU18/02922 | es |
dc.relation.projectID | FPU19/04361 | es |
dc.relation.publisherversion | https://dx.doi.org/10.1021/acs.joc.3c00564 | es |
dc.identifier.doi | 10.1021/acs.joc.3c00564 | es |
dc.journaltitle | Journal of Organic Chemistry | es |
dc.publication.volumen | 88 | es |
dc.publication.issue | 13 | es |
dc.publication.initialPage | 8674 | es |
dc.publication.endPage | 8689 | es |
dc.contributor.funder | Ministerio de Ciencia e Innovación (MICIN). España | es |
dc.contributor.funder | European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) | es |
dc.contributor.funder | Junta de Andalucía | es |
dc.contributor.funder | Universidad de Sevilla | es |