Fluorescent push-pull pH-responsive probes for ratiometric detection of intracellular pH

Document Type

Article

Publication Title

Organic and Biomolecular Chemistry

Abstract

A family of fluorescent push-pull pH-responsive probes based on 2-dicyanomethylidene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran as a strong electron acceptor group is described. Small structural variations allow obtaining pKa ranging from 4.8 to 8.6, underlining the role of the substituent in modulating the acidic properties. Remarkable changes in the optical properties (in particular the fluorescence intensity ratios) were observed as a function of pH. The most interesting probes with pKa close to neutrality were used for ratiometric imaging of intracellular pH. This journal is © the Partner Organisations 2014.

First Page

3641

Last Page

3648

DOI

10.1039/c4ob00147h

Publication Date

6-14-2014

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