A PCT-based, pyrene-armed calix[4]crown fluoroionophore

Jung Kyu Choi, Su Ho Kim, Juyoung Yoon, Keun Hyeung Lee, Richard A. Bartsch, Jong Seung Kim

Research output: Contribution to journalArticle

134 Citations (Scopus)

Abstract

A photoinduced charge transfer (PCT)-based 1,3-alternate calix[4]crown fluoroionophore containing two cation recognition sites, a crown ether ring and two facing pyreneamide groups, is synthesized. Upon addition of K+, Pb2+, or Cu2+, wavelength changes are observed in both the fluorescence and absorption spectra, but with different binding modes. With K+, fluorescence emissions of the ligand scarcely change, while addition of Pb2+ or Cu2+ produces a remarkable change in both the excimer and monomer emissions. The observed data indicate that the metal cation is encapsulated in the crown-5 ring for K+ and by the two facing amide groups in the latter case, which is verified by a metal ion exchange experiment. The wavelength shifts in both fluorescence and absorption spectra upon addition of Cu2+ show that, in contrast to Pb2+, Cu 2+ interacts with the nitrogen atoms of the amide groups, resulting in a PCT mechanism.

Original languageEnglish
Pages (from-to)8011-8015
Number of pages5
JournalJournal of Organic Chemistry
Volume71
Issue number21
DOIs
Publication statusPublished - 2006 Oct 13
Externally publishedYes

Fingerprint

Crowns
Charge transfer
Fluorescence
Amides
Cations
Absorption spectra
Metals
Crown Ethers
Wavelength
Ion Exchange
Metal ions
Ion exchange
Nitrogen
Monomers
Ligands
Atoms
pyrene
Experiments

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Choi, J. K., Kim, S. H., Yoon, J., Lee, K. H., Bartsch, R. A., & Kim, J. S. (2006). A PCT-based, pyrene-armed calix[4]crown fluoroionophore. Journal of Organic Chemistry, 71(21), 8011-8015. https://doi.org/10.1021/jo060981j

A PCT-based, pyrene-armed calix[4]crown fluoroionophore. / Choi, Jung Kyu; Kim, Su Ho; Yoon, Juyoung; Lee, Keun Hyeung; Bartsch, Richard A.; Kim, Jong Seung.

In: Journal of Organic Chemistry, Vol. 71, No. 21, 13.10.2006, p. 8011-8015.

Research output: Contribution to journalArticle

Choi, JK, Kim, SH, Yoon, J, Lee, KH, Bartsch, RA & Kim, JS 2006, 'A PCT-based, pyrene-armed calix[4]crown fluoroionophore', Journal of Organic Chemistry, vol. 71, no. 21, pp. 8011-8015. https://doi.org/10.1021/jo060981j
Choi, Jung Kyu ; Kim, Su Ho ; Yoon, Juyoung ; Lee, Keun Hyeung ; Bartsch, Richard A. ; Kim, Jong Seung. / A PCT-based, pyrene-armed calix[4]crown fluoroionophore. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 21. pp. 8011-8015.
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