Synthesis of Oligophenylene-Substituted Calix[4]crown-4s and Their Silver(I) Ion-Induced Nanocones Formation

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal

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Author(s)

  • Man Shing Wong
  • Ping Fang Xia
  • Xiao Hua Sun
  • Wai Yeung Wong
  • Shaomin Shuang

Detail(s)

Original languageEnglish
Pages (from-to)940-946
Journal / PublicationJournal of Organic Chemistry
Volume71
Issue number3
Publication statusPublished - 1 Feb 2006
Externally publishedYes

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.

Citation Format(s)

Synthesis of Oligophenylene-Substituted Calix[4]crown-4s and Their Silver(I) Ion-Induced Nanocones Formation. / Wong, Man Shing; Xia, Ping Fang; Lo, Pik Kwan; Sun, Xiao Hua; Wong, Wai Yeung; Shuang, Shaomin.

In: Journal of Organic Chemistry, Vol. 71, No. 3, 01.02.2006, p. 940-946.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal