Novel rhodamine dye with large Stokes shifts by fusing the 1,4-diethylpiperazine moiety and its applications in fast detection of Cu2+

Abstract

Rhodamine dyes were widely developed for designing probes due to their excellent photophysical properties and biocompatibility. However, traditional rhodamine dyes still bear major drawbacks of short emission wavelengths (<600 nm) and narrow Stokes shifts (<30 nm), which limit their biological imaging applications. Herein, we reported a novel mitochondria-targeted fluorescent dye JRQ with near-infrared (NIR) emission wavelength and improved Stokes shift (63 nm) by tuning the donor–acceptor–donor (D–A–D) character of the rhodamine skeleton. As expected, JRQ exhibited multiple excellent properties and could accumulate in mitochondria, and can therefore be used as a signal reporter for the design of fluorescent probes by taking advantage of the fluorescence controlled mechanism of the ring opening and closing chemical processes of the spirolactone platform. By using JRQ as a precursor, a highly sensitive fluorescent probe JRQN for the fast detection of mitochondrial Cu²⁺ ions was synthesized based on the Cu²⁺-triggered specific hydrolysis mechanism because mitochondria are an important reservoir of intracellular Cu²⁺. We expect that the Stokes shift increase of rhodamine dyes via tuning the donor–acceptor–donor (D–A–D) character of the rhodamine skeleton will provide a novel synthetic approach for the development of rhodamine dyes and expansion of their applications.