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

Yumei Zhu; Jorge Escorihuela; Haiying Wang; Andrew C-H Sue; Han Zuilhof

doi:10.3390/molecules28207009

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

Molecules. 2023 Oct 10;28(20):7009. doi: 10.3390/molecules28207009.

Authors

Yumei Zhu¹, Jorge Escorihuela², Haiying Wang¹, Andrew C-H Sue³, Han Zuilhof^{1

4}

Affiliations

¹ School of Pharmaceutical Science & Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, China.
² Departamento de Química Orgánica, Universitat de València, Avda. Vicente Andrés Estellés s/n, 46100 València, Spain.
³ College of Chemistry and Chemical Engineering, Xiamen University, 422 Siming South Road, Siming District, Xiamen 361005, China.
⁴ Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands.

Abstract

We developed an improved, robust synthesis of a series of pillar[6]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-Ag₂ 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.

Keywords: host–guest interactions; metal ion inclusion; pillararenes; supramolecular chemistry; tunable cavity.

Abstract

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