Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes

We developed an improved, robust synthesis of a series of pillar[<i>6</i>]arenes with a varying number (0–3) of quinone moieties in the ring. This easy-to-control variation yielded a gradually less electron-rich cavity in going from zero to three quinone units, as shown from the strength...

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Main Authors: Yumei Zhu, Jorge Escorihuela, Haiying Wang, Andrew C.-H. Sue, Han Zuilhof
Format: Article
Language:English
Published: MDPI AG 2023-10-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/20/7009
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author Yumei Zhu
Jorge Escorihuela
Haiying Wang
Andrew C.-H. Sue
Han Zuilhof
author_facet Yumei Zhu
Jorge Escorihuela
Haiying Wang
Andrew C.-H. Sue
Han Zuilhof
author_sort Yumei Zhu
collection DOAJ
description We developed an improved, robust synthesis of a series of pillar[<i>6</i>]arenes with a varying number (0–3) of quinone moieties in the ring. This easy-to-control variation yielded a gradually less electron-rich cavity in going from zero to three quinone units, as shown from the strength of host–guest interactions with silver ions. Such macrocycle-Ag<sub>2</sub> complexes themselves were shown to display an unprecedented, sharp distinction between terminal alkynes, which strongly bound to such complexes, and internal alkynes, internal alkenes and terminal alkenes, which do hardly bind.
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spelling doaj.art-a05f1ac49e5147f5aef7caa505ac5e3b2023-11-19T17:31:23ZengMDPI AGMolecules1420-30492023-10-012820700910.3390/molecules28207009Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-AlkynesYumei Zhu0Jorge Escorihuela1Haiying Wang2Andrew C.-H. Sue3Han Zuilhof4School of Pharmaceutical Science & Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, ChinaDepartamento de Química Orgánica, Universitat de València, Avda. Vicente Andrés Estellés s/n, 46100 València, SpainSchool of Pharmaceutical Science & Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, ChinaCollege of Chemistry and Chemical Engineering, Xiamen University, 422 Siming South Road, Siming District, Xiamen 361005, ChinaSchool of Pharmaceutical Science & Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, ChinaWe developed an improved, robust synthesis of a series of pillar[<i>6</i>]arenes with a varying number (0–3) of quinone moieties in the ring. This easy-to-control variation yielded a gradually less electron-rich cavity in going from zero to three quinone units, as shown from the strength of host–guest interactions with silver ions. Such macrocycle-Ag<sub>2</sub> complexes themselves were shown to display an unprecedented, sharp distinction between terminal alkynes, which strongly bound to such complexes, and internal alkynes, internal alkenes and terminal alkenes, which do hardly bind.https://www.mdpi.com/1420-3049/28/20/7009pillarareneshost–guest interactionsmetal ion inclusiontunable cavitysupramolecular chemistry
spellingShingle Yumei Zhu
Jorge Escorihuela
Haiying Wang
Andrew C.-H. Sue
Han Zuilhof
Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
Molecules
pillararenes
host–guest interactions
metal ion inclusion
tunable cavity
supramolecular chemistry
title Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
title_full Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
title_fullStr Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
title_full_unstemmed Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
title_short Tunable Supramolecular Ag<sup>+</sup>-Host Interactions in Pillar[<i>n</i>]arene[<i>m</i>]quinones and Ensuing Specific Binding to 1-Alkynes
title_sort tunable supramolecular ag sup sup host interactions in pillar i n i arene i m i quinones and ensuing specific binding to 1 alkynes
topic pillararenes
host–guest interactions
metal ion inclusion
tunable cavity
supramolecular chemistry
url https://www.mdpi.com/1420-3049/28/20/7009
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