Issue 5, 2013

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

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 PPh3. 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.

Graphical abstract: A depropargylation-triggered fluorescence “turn-on” probe for the detection of Pd2+ based on a bispropargylamine–rhodamine conjugate

Supplementary files

Article information

Article type
Paper
Submitted
27 Nov 2012
Accepted
10 Jan 2013
First published
10 Jan 2013

Analyst, 2013,138, 1564-1569

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

R. Balamurugan, C. Chien, K. Wu, Y. Chiu and J. Liu, Analyst, 2013, 138, 1564 DOI: 10.1039/C3AN36758D

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