Issue 2, 2015

Naphthalene diimides as red fluorescent pH sensors for functional cell imaging

Abstract

A small library of hydrosoluble naphthalene diimides (NDIs) was designed and synthesized, as cell permeable pH “turned-on” fluorescent sensors, for cellular applications. The NDIs exhibit a non-emitting twisted intramolecular charge transfer (TICT) state, which has been described by a DFT computational investigation. These NDIs do not emit as a free base, but they become strong emitters when protonated. Switching of the red emission was achieved in the pH window 2.5–6, tuning steric and electronic features of the amine moiety. The least acidic protonated NDI 5 (pKa 5.1), was investigated in normal and cancer cells. Its selective redistribution in cancer cells from acidic vesicular organelles to the cytoplasm and the nucleus describes an effective application of these NDIs as a valuable functional tool.

Graphical abstract: Naphthalene diimides as red fluorescent pH sensors for functional cell imaging

Supplementary files

Article information

Article type
Paper
Submitted
26 Sep 2014
Accepted
23 Oct 2014
First published
24 Oct 2014

Org. Biomol. Chem., 2015,13, 570-576

Author version available

Naphthalene diimides as red fluorescent pH sensors for functional cell imaging

F. Doria, M. Folini, V. Grande, G. Cimino-Reale, N. Zaffaroni and M. Freccero, Org. Biomol. Chem., 2015, 13, 570 DOI: 10.1039/C4OB02054E

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