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Control of the assembly of a cyclic hetero[4]pseudorotaxane from a self-complementary [2]rotaxane

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dc.contributor.authorSaura-Sanmartin, Adrian
dc.contributor.authorNicolas-Garcia, Tomas
dc.contributor.authorPastor, Aurelia
dc.contributor.authorQuiñonero, David
dc.contributor.authorAlajarin, Mateo
dc.contributor.authorMartinez-Cuezva, Alberto
dc.contributor.authorBerna, Jose
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2023-10-26T10:52:54Z
dc.date.available2023-10-26T10:52:54Z
dc.date.created2023
dc.date.issued2023-03-22
dc.description© 2023 The Authors. This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/ This document is the Published version that appeared in final form in Chemical Science. To access the final edited and published work see DOI: 10.1039/d3sc00886j
dc.description.abstractThe synthesis of a ditopic interlocked building-block and its self-assembly into a cyclic dimer is reported herein. Starting from a thread with two recognition sites, a three-component clipping reaction was carried out to construct a bistable [2]rotaxane. A subsequent Suzuki cross-coupling reaction allowed the connection of a second ring to that of the rotaxane, affording a self-complementary ditopic system. NMR studies were carried out to identify a cyclic hetero[4]pseudorotaxane as the main supramolecular structure in solution. Its assembly is the result of a positive cooperativity operating in the hydrogen-bonding-driven assembly of this mechanically interlocked supramolecule, as revealed by computational studies. The increase of the polarity of the solvent allows the disruption of the intercomponent interactions and the disassembly of the hetero[4]pseudorotaxane into the two interlocked units. The disassembly of the cyclic dimer was also achieved through a Diels–Alder reaction over the fumaramide binding site of the thread, triggering the translational motion of the entwined macrocycle to an adjacent glycylglycine-based station and precluding the supramolecular dimerization. The competitive molecular recognition of a guest molecule by one of the self-templating counterparts of the dimer also led to the controlled disassembly of the hetero[4]pseudorotaxane.es
dc.formatapplication/pdfes
dc.format.extent9es
dc.identifier.citationChemical Science, 2023, 14, 4143
dc.identifier.issn2041-6539
dc.identifier.urihttp://hdl.handle.net/10201/135145
dc.languageenges
dc.publisherRoyal Society of Chemistryes
dc.relationMICIN/AEI/10.13039/501100011033 (Project PID2020-113686GB-I00) Fundacion Seneca-CARM (Projects 20811/PI/18 and 21907/PI/22).es
dc.relation.requireshttp://hdl.handle.net/10201/135164
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleControl of the assembly of a cyclic hetero[4]pseudorotaxane from a self-complementary [2]rotaxanees
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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