dc.contributor.author |
Huerta, Elisa |
dc.contributor.author |
Serapian, Stefano Artin |
dc.contributor.author |
Santos, Eva |
dc.contributor.author |
Cequier, Enrique |
dc.contributor.author |
Bo, Carles |
dc.contributor.author |
de Mendoza, Javier |
dc.date.accessioned |
2018-01-15T16:04:19Z |
dc.date.accessioned |
2018-02-15T10:27:35Z |
dc.date.available |
2018-01-15T16:04:19Z |
dc.date.available |
2018-02-15T10:27:35Z |
dc.date.issued |
2016 |
dc.identifier.uri |
http://hdl.handle.net/2072/226328 |
dc.identifier.uri |
http://hdl.handle.net/2072/305764 |
dc.language.iso |
eng |
dc.publisher |
Wiley |
dc.relation |
MINECO |
dc.relation |
I+D+I Severo Ochoa Excellence Accreditation 2014–2018 |
dc.relation.ispartof |
Chem. Eur. J. |
dc.subject.other |
selective purification of fullerenes, supramolecular chemistry, DFT, density functional theory, NMR, circular dichroism |
dc.title |
Molecular Basis for the Recognition of Higher Fullerenes into Ureidopyrimidinone-Cyclotriveratrylene Self-Assembled Capsules |
dc.type |
info:eu-repo/semantics/article |
dc.relation.projectID |
CTQ2014-52824-R |
dc.relation.projectID |
SEV-2013-0319 |
dc.identifier.doi |
https://dx.doi.org/10.1002/chem.201601690 |
dc.rights.accessLevel |
info:eu-repo/semantics/openAccess |
dc.description.abstract |
Fullerenes C60, C70, and C84 may be readily encaged within a hydrogen-bonded dimeric capsule, based on two concave cyclotriveratrylene (CTV) scaffolds each bearing three self-complementary 2-ureido-4-[1H]-pyrimidinone (UPy) subunits. We herein report NMR and CD studies—complemented by dispersion-corrected density functional theory calculations—aiming to characterize such capsule-fullerene complexes both structurally and energetically. Six fullerenes are considered: in agreement with experiment, calculations find that encapsulation is most favorable for C84 (on a par with C90), and follows the trend C60<C70<C76<C78<C84≈C90. As also found by NMR, the most stable capsules are formed by monomers of identical stereochemistry; with UPy and the CTV’s OMe groups in mutual anti orientation; and UPy-CTV ethylene linkers within the capsular surface plane. Up to C78, encapsulation is favored by increasing host-guest contacts, but the trend is thereafter increasingly inhibited by growing capsule strain. |