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 journalArticlepeer-review

39 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

All Science Journal Classification (ASJC) codes

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

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