In this review we will explore recent advances in the design and application of excited-state intramolecular proton-transfer (ESIPT) based fluorescent probes. Fluorescence based sensors and imaging agents (probes) are important in biology, physiology, pharmacology, and environmental science for the selective detection of biologically and/or environmentally important species. The development of ESIPT-based fluorescence probes is particularly attractive due to their unique properties, which include a large Stokes shift, environmental sensitivity and potential for ratiometric sensing.

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Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

The development of an analytical method for selective and sensitive detection of chlortetracycline (CTC), an often overused broad spectrum antibiotic, is important and challenging in environmental and health monitoring. This paper reports a zinc based metal-organic framework of pyromellitic acid (Zn-BTEC), which has been found to greatly enhance the aggregation-induced emission (AIE) of chlortetracycline. The unique emission response of CTC on Zn-BTEC has been extensively examined and applied for the sensitive detection of CTC on the basis of fluorescence intensity of AIE, and a limit of detection (LOD) was estimated to be 28 nM. A rational mechanism has been proposed based on the porous structure of Zn-BTEC, and the CTC molecules would defuse into the rigid MOF structure and assemble or aggregate, leading to fluorescence enhancement of CTC. Interestingly, the Zn-BTEC materials could discriminate CTC from other TC antibiotics with high selectivity. We have further demonstrated that the Zn-BTEC materials are successfully applied for the sensitive and selective determination of CTC in real samples of fish and urine.

Metal-Organic Framework Enhances Aggregation-Induced Fluorescence of Chlortetracycline and the Application for Detection.

Excited‐State Intramolecular Proton Transfer (ESIPT) for Optical Sensing in Solid State

This paper demonstrated a high-performance ozone gas sensor based on metal-organic frameworks (MOFs)-derived In2O3 hollow microtubes decorated with ZnO nanoparticles. The microstructural and morphological features of as-synthesized In2O3/ZnO samples were characterized by various characterization methods, such as XRD, TG, SEM, TEM and XPS. The sensing properties of In2O3 hollow microtubes before and after modified by ZnO nanoparticles were investigated. The In2O3/ZnO composite shows an obvious enhancement in ozone gas sensing performance at the optimum working temperature of 150 °C. The In2O3/ZnO composite sensor shows much higher response (Rg/Ra = 26.12 @ 1 ppm ozone) in contrast with pure In2O3 (Rg/Ra = 14.08 @ 1 ppm ozone). In particular, the detection limit of the In2O3/ZnO sensor is as low as 25 ppb. The enhanced sensing performance of the In2O3/ZnO composite could be explained by the Zn2+ doping and heterojunction created at the In2O3/ZnO interface.

Ozone gas sensing properties of metal-organic frameworks-derived In2O3 hollow microtubes decorated with ZnO nanoparticles

Liver cancer is a kind of high mortality cancer due to the difficulty of early diagnosis. And according to the reports, the concentration of reactive oxygen species (ROS) was higher in cancer cells than normal cells. Therefore, developing an effective fluorescent probe for hepatoma-selective imaging of hypochlorous acid (HOCl) which is one of the vital ROS is of great importance for understanding the role of HOCl in liver cancer pathogenesis. However, the cell-selective fluorescent probe still remains a difficult task among current reports. Herein, a galactose-appended naphthalimide (Gal-NPA) with p-aminophenylether as a new receptor and galactose moiety as hepatoma targeting unit was synthesized and employed to detect endogenous HOCl in living HepG2 cells. This probe was proved to possess good water solubility and could respond specifically to HOCl. In addition, probe Gal-NPA could completely react to HOCl within 3 s meanwhile accompanied by tremendous fluorescence enhancement. The quantitative linear range between fluorescence intensities and the HOCl concentrations was 0 to 1 μM (detection limit = 0.46 nM). More importantly, fluorescence confocal imaging experiments showed that probe Gal-NPA could discriminate hepatoma cells over other cancer cells and simultaneously trace endogenous HOCl levels in living HepG2 cells. And we thus anticipate that probe Gal-NPA has the potential application for revealing the functions of HOCl in hepatoma cells.

Rational Design of a Hepatoma-Specific Fluorescent Probe for HOCl and Its Bioimaging Applications in Living HepG2 Cells

Ozone is widely used in air sterilization, food and medical disinfection in modern society, but high ozone levels in the living environment are considered harmful and have been associated with various respiratory diseases. Therefore, quick detection for ozone of part per million (ppm) levels is significant for living environment and an excited-state intramolecular proton transfer (ESIPT) compound has been synthesized. Due to an intrinsic excited-state intramolecular proton transfer (ESIPT) process, this “off-on” probe can fluoresce in the solid-state. This intrinsic fluorescent property makes it easy to detect lower concentration of ozone since the reaction product of probe can avoid being affected by pH and solubility through luminescence in the solid-state. The limit of gaseous ozone detection can be as low as 0.28 ppm for obviously distinguishable fluorescence colour from blue to cyan, showing that the probe can be useful for detecting ozone without the need of elaborate equipment.

A fluorescence probe for highly selective and sensitive detection of gaseous ozone based on excited-state intramolecular proton transfer mechanism

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A fluorescence probe for highly selective and sensitive detection of gaseous ozone based on excited-state intramolecular proton transfer mechanism