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


ABSTRACT: A long-lived aldol reaction-based iridium(III) chemosensor [Ir(ppy)2(5-CHOphen)]PF6 (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 sp2-hybridized carbonyl group into a sp3-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 1H 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.

SUBMITTER: Liu JB 

PROVIDER: S-EPMC5095674 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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

Liu Jin-Biao JB   Liu Li-Juan LJ   Dong Zhen-Zhen ZZ   Yang Guan-Jun GJ   Leung Chung-Hang CH   Ma Dik-Lung DL  

Scientific reports 20161104


A long-lived aldol reaction-based iridium(III) chemosensor [Ir(ppy)<sub>2</sub>(5-CHOphen)]PF<sub>6</sub> (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<sup>2</sup>-hybridized carbonyl group into a sp<sup>3</sup>-hybridized alcohol group infl  ...[more]

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