Synthesis of oligophenylene-substituted calix[4]crown-4s and their silver(I) ion-induced nanocones formation

Man Shing Wong, Ping Fang Xia, Pik Kwan Lo, Xiao Hua Sun, Wai Yeung Wong, Shaomin Shuang

Research output: Journal article publicationJournal articleAcademic researchpeer-review

25 Citations (Scopus)

Abstract

A novel series of oligophenylene OPP(n)-substituted calix[4]crown-4s bearing up to three phenylene units, 1a-d, has been efficiently synthesized by means of either microwave-assisted or silver(I) ion-assisted Pd-catalyzed Suzuki cross-coupling of tetraiodocalix[4]crown-4 and the corresponding oligophenylboronic acids. Complexation of OPP(n)-substituted calix[4]crown-4s with silver (I) ion was substantiated by 1H NMR spectroscopic and high-resolution ESI- or MALDI-TOF- MS studies. The weak binding affinities of OPP(n)-substituted calix[4]crown-4s for silver (I) ion, which were estimated from 1H NMR titrations with binding association in the range of 30-90 M-1, allows reversible disassembling in the presence of KI at ambient temperature. Remarkably, the single-crystal X-ray structures of OPP(n)-calix[4]crown-4-Ag+ complexes indicate the atypical silver (I) ion-crown ether binding mode resulting in the formation of rigid nanocones with volume created up to ∼1500 Å3. Our results suggested that despite the weak binding affinity of crown ether ligands for silver (I) ion, this weak interaction is still be useful as a tool to construct supramolecular architectures.
Original languageEnglish
Pages (from-to)940-946
Number of pages7
JournalJournal of Organic Chemistry
Volume71
Issue number3
DOIs
Publication statusPublished - 3 Feb 2006
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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