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Issue 5, 2018
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A “turn-on-and-off” pH sensitive BODIPY fluorescent probe for imaging E. coli cells

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Abstract

We report fluorescent turn-on-and-off pH BODIPY probes which show a drastic shift in pKa values upon introducing electron withdrawing substituents on the meso-phenyl ring. The sensors utilize 4-amino- and 4-hydroxyl groups as proton receptors and work by intramolecular photoinduced electron transfer (PET) under acidic pH conditions. The acid sensing mechanism is proven by 1H NMR, IR spectroscopic methods and electrochemical studies. Unlike previous reports, the pH response of the –OH group in compound 3 is due to the formation of –OH2+. Compounds 1 and 4 are highly selective to H+ over other metal ions and displayed good photostability and reversibility. The utility of acid sensitive behavior of 1 and 4 to visualize extreme acidity is also demonstrated using the model organism E. coli.

Graphical abstract: A “turn-on-and-off” pH sensitive BODIPY fluorescent probe for imaging E. coli cells

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Publication details

The article was received on 07 Nov 2017, accepted on 19 Jan 2018 and first published on 19 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04313A
Citation: New J. Chem., 2018,42, 3473-3482
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    A “turn-on-and-off” pH sensitive BODIPY fluorescent probe for imaging E. coli cells

    D. Prasannan and C. Arunkumar, New J. Chem., 2018, 42, 3473
    DOI: 10.1039/C7NJ04313A

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