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

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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
Issue number21
StatePublished - 13 Oct 2006


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