A depropargylation-triggered fluorescence "turn-on" probe for the detection of Pd2+ based on a bispropargylamine-rhodamine conjugate

Rathinam Balamurugan, Chih Chieh Chien, Kai Ming Wu, Yi Hong Chiu, Jui Hsiang Liu

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

A bis-propargyl-appended rhodamine B-based receptor BPRB has been synthesised that exhibits pronounced fluorescence enhancement in the presence of Pd2+ ions. The addition of Pd2+ enhanced the fluorescence intensity of BPRB by 113-fold (Φf = 0.37) and BPRB was found to exhibit high selectivity towards Pd2+ compared to a range of other metal ions. The enhancement of fluorescence was triggered by spirolactam ring opening followed by depropargylation of BPRB in the presence of Pd2+, as evidenced by FTIR and NMR analyses. BPRB was able to detect Pd0 without the addition of a reducing agent, and the emission intensity of BPRB-Pd0 was almost identical to that of BPRB-Pd2+; however, a rapid fluorescence response was observed in the presence of PPh 3. To explore the efficiency of the rhodamine unit, a bispropargyl derivative of cyclohexane (BPCH) was synthesised and the fluorescence response towards Pd2+ was examined and compared with BPRB, revealing that the rhodamine unit enhanced the fluorescence intensity by 500-fold. The fluorescence images of BPRB and BPRB-Pd2+ samples indicate that BPRB could be useful for imaging Pd2+ in living cells.

Original languageEnglish
Pages (from-to)1564-1569
Number of pages6
JournalAnalyst
Volume138
Issue number5
DOIs
Publication statusPublished - 2013 Mar 7

Fingerprint

Rhodamines
fluorescence
Fluorescence
probe
rhodamine B
Ions
fold
ion
Reducing Agents
Reducing agents
Fourier Transform Infrared Spectroscopy
Cyclohexane
detection
Metal ions
nuclear magnetic resonance
Metals
Cells
Nuclear magnetic resonance
Derivatives
Imaging techniques

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Environmental Chemistry
  • Spectroscopy
  • Electrochemistry

Cite this

Balamurugan, Rathinam ; Chien, Chih Chieh ; Wu, Kai Ming ; Chiu, Yi Hong ; Liu, Jui Hsiang. / A depropargylation-triggered fluorescence "turn-on" probe for the detection of Pd2+ based on a bispropargylamine-rhodamine conjugate. In: Analyst. 2013 ; Vol. 138, No. 5. pp. 1564-1569.
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A depropargylation-triggered fluorescence "turn-on" probe for the detection of Pd2+ based on a bispropargylamine-rhodamine conjugate. / Balamurugan, Rathinam; Chien, Chih Chieh; Wu, Kai Ming; Chiu, Yi Hong; Liu, Jui Hsiang.

In: Analyst, Vol. 138, No. 5, 07.03.2013, p. 1564-1569.

Research output: Contribution to journalArticle

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