Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts

We report the synthesis of an unprecedent mono-gold(I) phosphine complex based on a 'two wall' aryl-ethynyl extended calix[4]pyrrole. We describe and compare the binding properties of the parent 10α,20α-bis-aryl-ethynyl calix[4]pyrrole ligand and the prepared organometallic compound as rec...

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Detalles Bibliográficos
Autores: Sun, Qingqing, Aragay, Gemma, Pinto Martínez, Andrea, Aguiló Linares, Elisabet, Rodríguez Raurell, Laura, Ballester, Pablo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/159117
Acceso en línea:https://hdl.handle.net/2445/159117
Access Level:acceso abierto
Palabra clave:Pirroles
Química supramolecular
Compostos d'or
Pyrroles
Supramolecular chemistry
Gold compounds
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spelling Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride saltsSun, QingqingAragay, GemmaPinto Martínez, AndreaAguiló Linares, ElisabetRodríguez Raurell, LauraBallester, PabloPirrolesQuímica supramolecularCompostos d'orPyrrolesSupramolecular chemistryGold compoundsWe report the synthesis of an unprecedent mono-gold(I) phosphine complex based on a 'two wall' aryl-ethynyl extended calix[4]pyrrole. We describe and compare the binding properties of the parent 10α,20α-bis-aryl-ethynyl calix[4]pyrrole ligand and the prepared organometallic compound as receptors for tetraalkylammonium chloride salts in dichloromethane and acetone solutions. We describe the results of 1H NMR, UV-vis titrations and isothermal titration calorimetry (ITC) experiments in DCM and acetone solution, aiming at thermodynamically characterize the formed complexes. The obtained results indicate a noticeable decrease in the binding affinity of the chloride for the mono-gold(I) receptor 1 compared to the parent ligand 2. The increase in the negative value of the electrostatic surface potential at the center of the aromatic ring of the gold(I) meso-aryl-ethynyl substituent serves to explain the observed results and the presence in solution of the chloride complex of 1 as a mixture of two conformers.Wiley-VCH2020202120202020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion10 p.application/pdfhttps://hdl.handle.net/2445/159117Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1002/chem.201905160Chemistry-A European Journal, 2020, vol. 26, num. 15, p. 3348-3357https://doi.org/10.1002/chem.201905160(c) Wiley-VCH, 2020info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1591172026-05-29T05:05:01Z
dc.title.none.fl_str_mv Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
title Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
spellingShingle Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
Sun, Qingqing
Pirroles
Química supramolecular
Compostos d'or
Pyrroles
Supramolecular chemistry
Gold compounds
title_short Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
title_full Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
title_fullStr Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
title_full_unstemmed Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
title_sort Influence of the attachment of a gold(I) phosphine moiety at the upper rim of a calix[4]pyrrole on the binding of tetraalkylammonium chloride salts
dc.creator.none.fl_str_mv Sun, Qingqing
Aragay, Gemma
Pinto Martínez, Andrea
Aguiló Linares, Elisabet
Rodríguez Raurell, Laura
Ballester, Pablo
author Sun, Qingqing
author_facet Sun, Qingqing
Aragay, Gemma
Pinto Martínez, Andrea
Aguiló Linares, Elisabet
Rodríguez Raurell, Laura
Ballester, Pablo
author_role author
author2 Aragay, Gemma
Pinto Martínez, Andrea
Aguiló Linares, Elisabet
Rodríguez Raurell, Laura
Ballester, Pablo
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Pirroles
Química supramolecular
Compostos d'or
Pyrroles
Supramolecular chemistry
Gold compounds
topic Pirroles
Química supramolecular
Compostos d'or
Pyrroles
Supramolecular chemistry
Gold compounds
description We report the synthesis of an unprecedent mono-gold(I) phosphine complex based on a 'two wall' aryl-ethynyl extended calix[4]pyrrole. We describe and compare the binding properties of the parent 10α,20α-bis-aryl-ethynyl calix[4]pyrrole ligand and the prepared organometallic compound as receptors for tetraalkylammonium chloride salts in dichloromethane and acetone solutions. We describe the results of 1H NMR, UV-vis titrations and isothermal titration calorimetry (ITC) experiments in DCM and acetone solution, aiming at thermodynamically characterize the formed complexes. The obtained results indicate a noticeable decrease in the binding affinity of the chloride for the mono-gold(I) receptor 1 compared to the parent ligand 2. The increase in the negative value of the electrostatic surface potential at the center of the aromatic ring of the gold(I) meso-aryl-ethynyl substituent serves to explain the observed results and the presence in solution of the chloride complex of 1 as a mixture of two conformers.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/159117
url https://hdl.handle.net/2445/159117
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1002/chem.201905160
Chemistry-A European Journal, 2020, vol. 26, num. 15, p. 3348-3357
https://doi.org/10.1002/chem.201905160
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2020
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2020
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 10 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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