Cyclams bearing diametrically disubstituted pyrenes as Cu2+- and Hg2+-selective fluoroionophores

Mi Park Sang, Hee Kim Mi, Jong In Choe, Kyoung Tai No, Suk Kyu Chang

Research output: Contribution to journalArticle

141 Citations (Scopus)

Abstract

(Chemical Equation Presented) New cyclam derivatives having diametrically disubstituted pyrene fluorophores were prepared and their fluoroionophoric properties toward transition metal ions were investigated. The compounds exhibited significant selectivity toward Hg2+ and Cu2+ ions in switching-off type responses in aqueous methanol or acetonitrile solution. Dipyrene-diamide derivative 3, having extra binding sites of the amide function, exhibited more pronounced chemosensing behavior toward Hg 2+ and Cu2+ ions than its parent, dipyrene derivative 2. Detection limits for the analysis of Hg2+ and Cu2+ ions of dipyrene-diamide derivative 3 were 1.45 × 10-6 and 1.30 × 10-6 M, respectively. The diametrically disubstituted dipyrene-cyclam 2 may be utilized as a new starting platform for the design of other supramolecular fluorescent signaling systems having switching or chemosensing behaviors toward transition metal ions.

Original languageEnglish
Pages (from-to)3550-3553
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number9
DOIs
Publication statusPublished - 2007 Apr 27

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Pyrenes
Macrocyclic Lactams
Bearings (structural)
Diamide
Derivatives
Ions
Transition metals
Metal ions
Fluorophores
Switching systems
Amides
Methanol
Binding Sites

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Sang, Mi Park ; Mi, Hee Kim ; Choe, Jong In ; No, Kyoung Tai ; Chang, Suk Kyu. / Cyclams bearing diametrically disubstituted pyrenes as Cu2+- and Hg2+-selective fluoroionophores. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 9. pp. 3550-3553.
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Cyclams bearing diametrically disubstituted pyrenes as Cu2+- and Hg2+-selective fluoroionophores. / Sang, Mi Park; Mi, Hee Kim; Choe, Jong In; No, Kyoung Tai; Chang, Suk Kyu.

In: Journal of Organic Chemistry, Vol. 72, No. 9, 27.04.2007, p. 3550-3553.

Research output: Contribution to journalArticle

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AB - (Chemical Equation Presented) New cyclam derivatives having diametrically disubstituted pyrene fluorophores were prepared and their fluoroionophoric properties toward transition metal ions were investigated. The compounds exhibited significant selectivity toward Hg2+ and Cu2+ ions in switching-off type responses in aqueous methanol or acetonitrile solution. Dipyrene-diamide derivative 3, having extra binding sites of the amide function, exhibited more pronounced chemosensing behavior toward Hg 2+ and Cu2+ ions than its parent, dipyrene derivative 2. Detection limits for the analysis of Hg2+ and Cu2+ ions of dipyrene-diamide derivative 3 were 1.45 × 10-6 and 1.30 × 10-6 M, respectively. The diametrically disubstituted dipyrene-cyclam 2 may be utilized as a new starting platform for the design of other supramolecular fluorescent signaling systems having switching or chemosensing behaviors toward transition metal ions.

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