An Aldol Reaction-Based Iridium(III) Chemosensor for the Visualization of Proline in Living Cells

Jin Biao Liu*, Li Juan Liu, Zhen Zhen Dong, Guan Jun Yang, Chung Hang Leung, Edmond Dik Lung MA

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

A long-lived aldol reaction-based iridium(III) chemosensor [Ir(ppy) 2 (5-CHOphen)]PF 6 (1, where ppy = 2-phenylpyridine and 5-CHOphen = 1,10-phenanthroline-5-carbaldehyde) for proline detection has been synthesized. The iridium(III) complex 1, incorporating an aldehyde group in N^N donor ligand, can take part in aldol reaction with acetone mediated by proline. The transformation of the sp 2-hybridized carbonyl group into a sp 3-hybridized alcohol group influences the metal-to-ligand charge-transfer (MLCT) state of the iridium(III) complex, resulting in a change in luminescence in response to proline. The interaction of the iridium(III) complex 1 with proline was investigated by 1 H NMR, HRMS and emission titration experiments. Upon the addition of proline to a solution of iridium(III) complex 1, a maximum 8-fold luminescence enhancement was observed. The luminescence signal of iridium(III) complex 1 could be recognized in strongly fluorescent media using time-resolved emission spectroscopy (TRES). The detection of proline in living cells was also demonstrated.

Original languageEnglish
Article number36509
JournalScientific Reports
Volume6
DOIs
Publication statusPublished - 4 Nov 2016

Scopus Subject Areas

  • General

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