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

Aluminum is a nonessential metal to which humans are frequently exposed. Aluminum in the food supply comes from natural sources, water used in food preparation, food ingredients, and utensils used during food preparations. The amount of aluminum in the diet is small, compared with the amount of aluminum in antacids and some buffered analgesics. The healthy human body has effective barriers (skin, lungs, gastrointestinal tract) to reduce the systemic absorption of aluminum ingested from water, foods, drugs, and air. The small amount of aluminum (<1%) that is systemically absorbed is excreted principally in the urine and, to a lesser extent, in the feces. No reports of dietary aluminum toxicity to healthy individuals exist in the literature. Aluminum can be neurotoxic, when injected directly into the brains of animals and when accidentally introduced into human brains (by dialysis or shrapnel). A study from Canada reports cognitive and other neurological deficits among groups of workers occupationally exposed to dust containing high levels of aluminum. While the precise pathogenic role of aluminum in Alzheimer's disease (AD) remains to be defined, present data do not support a causative role for aluminum in AD. High intake of aluminum from antacid for gastrointestinal ailments has not been reported to cause any adverse effects and has not been correlated with neurotoxicity or AD. Foods and food ingredients are generally the major dietary sources of aluminum in the United States. Cooking in aluminum utensils often results in statistically significant, but relatively small, increases in aluminum content of food. Common aluminum-containing food ingredients are used mainly as preservatives, coloring agents, leavening agents, anticaking agents, etc. Safety evaluation and approval of these ingredients by the Food and Drug Administration indicate that these aluminum-containing compounds are safe for use in foods.

Safty evaluation of dietary aluminum

Rationally designed multiple hydroxyl-group-based chemosensors L1-L4 containing arene-based fluorophores are presented for the selective detection of Al3+ and Ga3+ ions. Changes in the absorption and emission spectra of L1-L4 in ethanol were easily observable upon the addition of Al3+ and Ga3+ ions. Competitive binding studies, detection limits, and binding constants illustrate significant sensing abilities of these chemosensors with L4, showing the best results. The interaction of Al3+/Ga3+ ions with chemosensor L4 was investigated by fluorescence lifetime measurements, whereas Job's plot, high-resolution mass spectrometry, and 1H NMR spectral titrations substantiated the stoichiometry between L4 and Al3+/Ga3+ ions. The solution-generated [L-M3+] species further detected pyrophosphate ion (PPi) by exhibiting emission enhancement and a visible color change. The binding of Al3+/Ga3+ ions with chemosensor L4 was further supported by density functional theory studies. Reversibility for the detection of Al3+/Ga3+ ions was achieved by utilizing a suitable proton source. The multiionic response, reversibility, and optical visualization of the present chemosensors make them ideal for practical applications for real samples, which have been illustrated by paper-strip as well as polystyrene film-based detection.

Turn-On Fluorescent Sensors for the Selective Detection of Al3+ (and Ga3+) and PPi Ions.

A simple AIE-active fluorogen for relay recognition of Cu2+ and pyrophosphate through aggregation-switching strategy

A highly sensitive dual-channel chemical sensor for selective identification of B4O72−

Fluorescence sensor for sequential detection of zinc and phosphate ions.

A new 2-(2′-hydroxyphenyl)thiazole-4-carboxaldehyde based fluorescent probe (1) was designed and synthesized for sequential detection of Al3+ and F− ions in methanol. Probe 1 selectively detected Al3+ through a “switch on” response driven by the selective complexation of Al3+ ions with hemiacetal 2 formed from 1 in methanol. This process was mediated by combined excited-state intramolecular proton transfer (ESIPT) and chelation-induced enhanced fluorescence (CHEF) effects. Probe 2 bound Al3+ ions in a 1:1 stoichiometry with a good association constant of Ka = 9.1 × 104 M−1. The in situ generated 2·Al3+ (1:1) complex detected F− ions sequentially through a “switch off” response, with a 1:3 stoichiometry observed between 2·Al3+ (1:1) and F−. The lowest limits of detection (LODs) for Al3+ and F− ions in methanol were determined to be 9.24 × 10−7 and 1.4 × 10−5 M, respectively. The probe was also used to detect Al3+ ions with a slightly lower LOD and binding constant in aqueous methanol (1:19).

Highly selective fluorescent probe for switch-on Al3+ detection and switch-off F− detection

Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

Three novel fluorescent probes, 2-(2′-hydroxyphenyl)-4-chloromethylthiazole ( 1 ), 2-(2′-hydroxyphenyl)-4-hydroxymethylthiazole ( 3 ), and 2-(2′-hydroxyphenyl)-4-iodomethylthiazole ( 4 ) were designed for the sequential recognition of Ga 3+ and pyrophosphate ions in acetonitrile. Probe 1 selectively detected Ga 3+ through a “ switch on ” response, showing a good association constant ( K a  = 6.24 × 10 4  M −1 ) and binding with Ga 3+ ions in a 1:1 stoichiometry. An in situ generated 1-Ga 3+ (1:1) ensemble detected H 2 P 2 O 7 3– ions sequentially through a “ switch off” response. The “ switch on ” response occurred with selective complexation of Ga 3+ ions due to combined excited state intramolecular proton transfer (ESIPT) and chelation induced enhanced fluorescence (CHEF) effects. An ensemble of 1 and gallium(III) was more selective for pyrophosphate ions than any other anion.

Fluorescent probe for sequential recognition of Ga3+ and pyrophosphate anions

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Fluorescence sensor for sequential detection of zinc and phosphate ions.

Highly selective fluorescent probe for switch-on Al3+ detection and switch-off F− detection

Highly selective fluorescent probe for sequential recognition of copper(II) and iodide ions

Fluorescent probe for sequential recognition of Ga3+ and pyrophosphate anions