Ratiometric and selective fluorescent chemodosimeter for Cu(II) by Cu(II)‐induced oxidation

Abstract

A new rhodamine derivative, rhodamine B 4-N,N-dimethylaminobenzaldehyde hydrazone (1), was designed for ratiometric sensing of Cu(II) selectively. A red-shift from 515 to 585 nm was observed in the fluorescence spectrum when Cu(II) was added to 1 in acetonitrile. Other metal ions of interest showed no ratiometric response. The interaction between Cu(II) and 1 was found to be the Cu(II)-induced oxidation of 1.

Fluorescent salicylaldehyde hydrazone as selective chemosensor for Zn2+ in aqueous ethanol: a ratiometric approach

“…In our previous work, rhodamine-based chemosensors were investigated. (40)(41)(42)(43)(44) Most of them exhibit fl uorescence enhancement of metal ions complex. (40)(41)(42)(43) However, rhodamine B 4-N,N-dimethylaminobenzaldehyde hydrazone displayed a ratiometric fl uorescent response to Cu 2+ in acetonitrile through metalinduced oxidation mechanism, (44) and its oxidation product was found to be slowly hydrolyzed to rhodamine B by trace water from hydrated salts or solvent.…”

A rhodamine‐triazole fluorescent chemodosimeter for Cu2+ detection and its application in bioimaging

“…For Czarnik's rhodamine hydrazide, Cu 2+ promotes a hydrolytic reaction and results in an enhanced fluorescence emission but the chemical probe was later reported to react with Hg 2+ preferentially . Other Cu 2+ ‐selective rhodamine hydrazide derivatives have also been reported as well as rhodamine hydrazide conjugated with different receptors including isothiocyanate, 4‐(dimethylamino)benzaldehyde, sulfonyl, acyl, phenyl, pyridine, semicarbazide, thiosemicarbazide, vanillic aldehyde, 4‐chloro‐7‐nitro‐2,1,3‐benzoxadiazole, 4‐(diphenylamino)benzaldehyde, 1,4‐(5′‐ethynylsalicyaldehyde)‐ N ‐butyl‐1,8‐naphthalimides and the o ‐pyridylaldehyde group have been synthesized to explore the binding affinity for Cu 2+ . Significantly, 1,2,3‐triazole based on click chemistry plays various roles in metal sensing such as a multidentate motif for metal ions, a linker between a binding site and a reporter or as a part of a conjugated fluorophore .…”

“…benzaldehyde, [30] sulfonyl, [31] acyl, [32] phenyl, [33] pyridine, [34] semicarbazide, [35] thiosemicarbazide, [36] vanillic aldehyde, [37] 4-chloro-7-nitro-2,1,3-benzoxadiazole, [38] 4-(diphenylamino)benzaldehyde, [39] 1,4-(5′-ethynylsalicyaldehyde)-N-butyl-1,8-naphthalimides [40] and the o-pyridylaldehyde [41] group have been synthesized to explore the binding affinity for Cu 2+ . Significantly, 1,2,3-triazole based on click chemistry plays various roles in metal sensing such as a multidentate motif for metal ions, a linker between a binding site and a reporter or as a part of a conjugated fluorophore.…”

A New, Highly Potent 1,8‐Naphthalimide‐based Fluorescence “Turn off” Chemosensor Capable of Cu2+ Detection in China's Yellow River Water Samples

“…[28][29][30][31][32][33][34][35][36][37] Consequently, 1,8-naphthalimide derivatives have been found to be great applications for the generation of liquid crystal displays, laser active media, fluorescent markers in biology, photo-induced electron transfer (PET) chemosensors, electroluminescent materials, and fluorescence switches and chemosensors. [38][39][40][41][42] To date, researchers from across the globe have performed well with regard to the design and synthesis of Cu 2+ -selective fluorescence "turn off" chemosensors, with some of those findings referenced, [43][44][45][46][47][48][49][50][51][52] yet there are many milestones uncovered in the science of the design and development of Cu 2+ -selective chemosensors.…”