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RSC Advances · 2016 ·Vol. 6 ·期 68 ·63874-63879 · IF 3.289

Synthesis and optical properties of aggregation-induced emission (AIE) molecules based on the ESIPT mechanism as pH- and Zn2+-responsive fluorescent sensors

Liqiang Yan,Tingting Qing,Renjie Li,Zhongwei Wang,Zhengjian Qi

A series of schiff base derivatives with salicylaldehyde moieties were designed and synthesized. These materials exhibit typical AIE properties and high fluorescence quantum yields in an aggregated state based on the excited-state intramolecular proton transfer (ESIPT) mechanism. Then, the effect of substituted group types and positions on the fluorescence of these novel compounds was investigated through fluorescence spectra analysis and theoretical calculations. And it was found that the salicylaldehyde derivatives can be used as potential pH and Zn2+ sensors.

研究领域: 化学 · 材料科学 · 分析化学
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FOOD CHEMISTRY · 2025 · IF 9.8

New silicon nanoparticles for “turn-on” detection of salicylaldehyde in food based on ESIPT mechanism

Jialu Zhang,Yu Fu,Peng Chen,Bowen Liu,Cuiling Ren

Salicylaldehyde is a significant fine chemical product utilized in the flavoring of various foods, excessive intake of salicylaldehyde is detrimental to human health. Its accurate quantitative detection holds considerable importance. Compared with “turn-off” probes, the “turn-on”one allow for more sensitive detection. New silicon nanoparticles (D-SiNPs) which can be used to detect salicylaldehyde by “turn-on” mode were prepared in this work. This D-SiNPs demonstrates highly stability, selectivity and sensitivity. Within the concentration range of 5–50 μM, salicylaldehyde concentration exhibits a strong linear relationship with fluorescence intensity, the limit of detection is calculated to be 0.97 μM. It can be applied to detect salicylaldehyde in baked goods and beverages, achieving good recoveries. These results are highly satisfactory. The detect mechanism was investigated systemetically, the results illustrates this detection is based on Schiff reaction between the amino groups of silicon nanoparticles and aldehyde group of salicylaldehyde, which satisfies the ESIPT mechanism.

研究领域: 分析化学 · 食品科学 · 生物医学工程
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Multiple Applications of Chiral Self-Assembled H8–BINOL Nanoprobes with AIE-ESIPT Characteristics: Chiral Switching and pH Visualization Detection

Rong Wang,Kaiyue Song,Lixue Yang,Yue Sun,Xiaoxia Sun,Yu Hu

R-BTOBD exhibited significant aggregation-induced Emission (AIE) characteristics, including high brightness (αAIE ≈ 40), robust light stability, a substantial Stokes shift (128 nm), and a high signal-to-noise ratio, effectively overcoming aggregation-caused quenching (ACQ). Derived from the axially chiral R-H8–BINOL, R-BTOBD was synthesized via nucleophilic cyclization and exhibited pronounced self-assembly properties. Through robust intra- and intermolecular hydrogen bonding interactions, R-BTOBD formed diverse supramolecular structures, including spherical flower-like aggregates, hollow-core triangular tubules, hexagonal tubules, and irregular white block-like stacks. The specific morphology was influenced by factors such as solvent and pH. For fluorescence applications, R-BTOBD can be employed as an effective visual pH detector through an AIE-enhanced excited-state intramolecular proton transfer (AIE-ESIPT) mechanism. When incorporated into pH paper, it exhibited a bright yellow fluorescence across a wide pH range (pH 1–11), transitioning to an intense bright blue fluorescence under strongly basic conditions (pH 12–14). In chiral applications, R-BTOBD demonstrated potential as a chiral switching agent, leveraging the pronounced changes and inversions in its circular dichroism (CD) signals under varying aggregation states and pH conditions. Additionally, it serves as a specific chiral enantioselective fluorescence probe for l-lysine, demonstrating high efficiency and a low detection limit. Given its exceptional fluorescence and chiral properties, this fluorescent material has significant potential for diverse applications in fluorescence, chirality, and visual inspection.

研究领域: 材料科学 · 分析化学 · 生物化学
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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 14 ·6916-6923 · IF 3.3

An “AIE + ESIPT” mechanism-based benzothiazole-derived fluorescent probe for the detection of Hg2+ and its applications

Yanru Huang,Ying Li,Yang Li,Keli Zhong,Lijun Tang

Mercury ion (Hg2+) contamination is very hazardous and harmful to the natural environment and human health. The development of small molecule fluorescent probes for the rapid detection of Hg2+ is of great significance. In the present work, an “AIE + ESIPT” mechanism-based benzothiazole derived fluorescent probe was applied to Hg2+ detection and displayed excellent selectivity, good anti-interference ability, low detection limit (2.85 × 10−9 M), and a large Stokes shift (170 nm) in the DMF/H2O mixture solution with fw = 60% H2O volume fraction. The fluorescence response mechanism, involving the desulfurization reaction of O-(2-(benzo[d]thiazol-2-yl)-6-formyl-4-methylphenyl)dimethylcarbamothioate (probe L) with Hg2+ to release the “AIE + ESIPT” fluorophore, was well established based on the UV-vis, 1H NMR, and HRMS spectral analyses. The practical application evaluation indicates that probe L could be used to precisely determine Hg2+ in live cell imaging, natural water, and seafood samples.

研究领域: 分析化学 · 环境科学 · 生物医学
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BIOORGANIC CHEMISTRY · 2021 · IF 5.275

ESIPT-based fluorescent probe for bioimaging and identification of group IIIA ions in live cells and zebrafish

Qinxiang Zheng,Feng Ding,Xiaojuan Hu,Jiayao Feng,Jianliang Shen,Xiaojun He

Aluminum (Al), gallium (Ga), indium (In) are three essential elements in group IIIA of the periodic table, which all share similar chemical properties and are also vital in many aspects of bio- and environmental systems. Proper control of their levels is thus necessary as overexposure to them has been linked to onsets of many diseases. Fluorescence based molecular probes have always been the driving horse for detecting vital ions including group IIIA ions. However, only a few such probes have been reported so far and all of them are faced with one or more shortcomings such as not very high sensitivity, incapability to detect multiple ions simultaneously, and poor cell penetration abilities due to emitted fluorescence at shorter wavelengths. To meet those challenges, we herein presented the successful development and application of a novel group IIIA ions fluorescent probe, NBD-hnap , in live RAW264.7 cell and zebrafish models, especially the imaging of ocular tumor cell OCM-1 (human choroid melanoma cells). NBD-hnap was synthesized by a simple conjugation of NBD and hnap molecules under suitable conditions. Subsequent experimental analysis and theoretical calculations confirmed that NBD-hnap forms a 1:1 chelate with each of three selected group IIIA ions. Further evaluation proved that NBD-hnap can realize highly sensitive [LODs of 113, 82 and 150 nM for Al(III), Ga(III), and In(III) respectively in aqueous solutions] and highly selective (over a dozen of interfering cations) through an ESIPT-based fluorescent sensing mechanism with strong far-red emission around 640 nm. Those value merits make NBD-hnap superior to other group IIIA ion probes reported before and NBD-hnap is thus expected to find wider and greater applications in the near future.

CAS / MDL: 7784-27-2 207398-97-8
研究领域: 分析化学 · 生物医学工程 · 环境科学
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