Issue 20, 2013

A new turn-on fluorescent chemosensor based on diketopyrrolopyrrole (DPP) for imaging Zn2+ in living cells

Abstract

A new turn-on fluorescent chemosensor, DPPL1, was rationally designed and synthesized based on diketopyrrolopyrrole (DPP), which presented high sensitivity and selectivity for Zn2+. Specifically, DPPL1 presented a large emission enhancement and a 70 nm blue-shift upon Zn2+ binding. 1H NMR titrations, studies into the pH effects and DFT calculations further proved that this phenomenon was due to both photo-induced electron transfer (PET) and intra-molecular charge transfer (ICT) processes. More importantly, DPPL1 was successfully used for imaging Zn2+ in living HeLa cells. To the best of our knowledge, this is the first DPP-based fluorescent chemosensor to recognize Zn2+ ions in living cells with a large blue-shift and a fluorescent enhancement based on both photo-induced electron-transfer (PET) and intramolecular charge-transfer (ICT) effects. Meanwhile, we have also provided a new effective platform for the development of fluorescent chemosensors for other analytes.

Graphical abstract: A new turn-on fluorescent chemosensor based on diketopyrrolopyrrole (DPP) for imaging Zn2+ in living cells

Supplementary files

Article information

Article type
Paper
Submitted
29 Apr 2013
Accepted
26 Jul 2013
First published
29 Jul 2013

Analyst, 2013,138, 6163-6170

A new turn-on fluorescent chemosensor based on diketopyrrolopyrrole (DPP) for imaging Zn2+ in living cells

G. Zhang, H. Li, S. Bi, L. Song, Y. Lu, L. Zhang, J. Yu and L. Wang, Analyst, 2013, 138, 6163 DOI: 10.1039/C3AN00873H

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