CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif

[Image: see text] The synthesis of new triphenylphosphonium-capped cucurbit[7]uril (CB[7])- and cucurbit[8]uril (CB[8])-based [2]rotaxanes was achieved by a simultaneous threading-capping strategy. While the use of CB[7] produced the designed [2]rotaxane, attempts to obtain the CB[8] analogue were u...

Descripción completa

Detalles Bibliográficos
Autores principales: Neira, Iago, Peinador, Carlos, García, Marcos D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9251766/
https://www.ncbi.nlm.nih.gov/pubmed/35514222
http://dx.doi.org/10.1021/acs.orglett.2c01028
_version_ 1784740102253051904
author Neira, Iago
Peinador, Carlos
García, Marcos D.
author_facet Neira, Iago
Peinador, Carlos
García, Marcos D.
author_sort Neira, Iago
collection PubMed
description [Image: see text] The synthesis of new triphenylphosphonium-capped cucurbit[7]uril (CB[7])- and cucurbit[8]uril (CB[8])-based [2]rotaxanes was achieved by a simultaneous threading-capping strategy. While the use of CB[7] produced the designed [2]rotaxane, attempts to obtain the CB[8] analogue were unsuccessful due to the unexpected strong interaction found between the host and the phosphonium caps leading to pseudo-heteroternary host–guest complexes. This unusual binding motif has been extensively studied experimentally, with results in good agreement with those obtained by dispersion-corrected DFT methods.
format Online
Article
Text
id pubmed-9251766
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-92517662022-07-05 CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif Neira, Iago Peinador, Carlos García, Marcos D. Org Lett [Image: see text] The synthesis of new triphenylphosphonium-capped cucurbit[7]uril (CB[7])- and cucurbit[8]uril (CB[8])-based [2]rotaxanes was achieved by a simultaneous threading-capping strategy. While the use of CB[7] produced the designed [2]rotaxane, attempts to obtain the CB[8] analogue were unsuccessful due to the unexpected strong interaction found between the host and the phosphonium caps leading to pseudo-heteroternary host–guest complexes. This unusual binding motif has been extensively studied experimentally, with results in good agreement with those obtained by dispersion-corrected DFT methods. American Chemical Society 2022-05-06 2022-07-01 /pmc/articles/PMC9251766/ /pubmed/35514222 http://dx.doi.org/10.1021/acs.orglett.2c01028 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Neira, Iago
Peinador, Carlos
García, Marcos D.
CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title_full CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title_fullStr CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title_full_unstemmed CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title_short CB[7]- and CB[8]-Based [2]-(Pseudo)rotaxanes with Triphenylphosphonium-Capped Threads: Serendipitous Discovery of a New High-Affinity Binding Motif
title_sort cb[7]- and cb[8]-based [2]-(pseudo)rotaxanes with triphenylphosphonium-capped threads: serendipitous discovery of a new high-affinity binding motif
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9251766/
https://www.ncbi.nlm.nih.gov/pubmed/35514222
http://dx.doi.org/10.1021/acs.orglett.2c01028
work_keys_str_mv AT neiraiago cb7andcb8based2pseudorotaxaneswithtriphenylphosphoniumcappedthreadsserendipitousdiscoveryofanewhighaffinitybindingmotif
AT peinadorcarlos cb7andcb8based2pseudorotaxaneswithtriphenylphosphoniumcappedthreadsserendipitousdiscoveryofanewhighaffinitybindingmotif
AT garciamarcosd cb7andcb8based2pseudorotaxaneswithtriphenylphosphoniumcappedthreadsserendipitousdiscoveryofanewhighaffinitybindingmotif

Ejemplares similares