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ESIPT
DYES AND PIGMENTS · 2017 · IF 3.473

A far-red ratiometric fluorescent probe for SO2 derivatives based on the ESIPT enhanced FRET platform with improved performance

Dong-Peng Li,Xian-Jing Han,Ze-Quan Yan,Yun Cui,Jun-Ying Miao,Bao-Xiang Zhao

A ratiometric fluorescent probe (L-HF3) based on an efficient FRET platform constructed by 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) and 3-hydroxyflavone (HF) fluorophores for detection of sulfur dioxide derivatives (HSO 3 − /SO 3 2− ) was developed. The probe featured very large (pseudo) Stokes shifts , good selectivity and high sensitivity, high FRET efficiency and high resolution of the emission bands. The probe was also mitochondria-targeted and could detect exogenous and endogenous bisulfite in living cells.

研究领域: 生物化学 · 分子生物学 · 细胞生物学
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JOURNAL OF MOLECULAR LIQUIDS · 2019 · IF 4.561

Facile fabrication and biological imaging applications of salicylaldehyde based fluorescent organic nanoparticles with aggregation-induced emission and ESIPT feature

Saijiao Yang,Meiying Liu,Liucheng Mao,Dazhuang Xu,Hongye Huang,Junyu Chen,Yuanqing Wen,Fengjie Deng,Xiaoyong Zhang,Yen Wei

A novel AIE-active fluorogen with large Stokes shift and polymerizable group was synthesized through a one-step conjugation of 4-allyloxy-2-hydroxybenzophenone using hydrazine monohydrate. The obtained 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(phenylmethanylylidene))bis(3-(allyloxy)phe-nol) (named as HDPMA) shows AIE feature through excited-state intramolecular proton transfer (ESIPT) mechanism. To examine its potential biomedical applications, the hydrophobic HDPMA was copolymerized with a commercial available, hydrophilic and biocompatible monomer hydrophilic poly(ethylene glycol) methyl ether methacrylate (PEGMA) through reversible addition-fragmentation chain transfer (RAFT) polymerization. The successful synthesis of the HDPMA and final AIE-active poly(PEGMA- co -HDPMA) copolymers was evidenced by a series of characterization techniques. After self-assembly, the amphiphilic poly(PEGMA- co -HDPMA) copolymers could form uniform spherical micelles and showed high water dispersibility, bright yellow-green fluorescence, preeminent photostability, low critical micelle concentration. More importantly, poly(PEGMA- co -HDPMA) FONs show outstanding biocompatibility and low cytotoxicity. With these noticeable superiorities, poly(PEGMA- co -HDPMA) FONs will become promising candidates in biochemical sensing analysis, and cell imaging, even applied in more various important fields.

研究领域: 材料科学 · 生物医学工程 · 化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2026 · IF 4.8

Visualization of mitochondrial monoamine oxidase dynamics in live cells and DILI via a ratiometric NIR probe with “ICT+ESIPT” mechanism

Ting Cao,Mengjin Li,Hong Ma,Zhefeng Fan

Monoamine oxidase (MAOs) is a key enzyme that maintains amine homeostasis and participates in liver pathological processes. Real time in situ monitoring of its activity is crucial for elucidating the mechanism of drug-induced liver injury (DILI). This study successfully constructed a ratio type fluorescent probe Cy-1 with mitochondrial targeting ability and near-infrared emission characteristics. This probe is based on MAOs catalyzed oxidative deamination reaction, and achieves fluorescence response through a clever “ICT (Intramolecular Charge Transfer) + ESIPT (Excited-State Intramolecular Proton Transfer)” dual mechanism, producing significant ratiometric signal changes in the near-infrared region. Experiments have shown that Cy-1 has a wide linear range (10–115 μg/mL), high sensitivity (0.86 μg/mL), and high selectivity in vitro, and can specifically localize to mitochondria. The probe was successfully used for in situ differential monitoring of endogenous MAOs activity in living cells, and visualized semi quantitative monitoring of MAOs activity changes in vivo was achieved in an acetaminophen (APAP) induced drug-induced liver injury (DILI) model. Cy-1 is expected to become a powerful chemical tool for understanding the mechanisms of MAOs in physiological and pathological processes, especially in the occurrence and development of diseases such as liver injury, as well as evaluating the efficacy of related drugs.

CAS / MDL: 555-57-7 17780-72-2
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2026 · IF 4.4

An AIE-active NIR Ratiometric probe based on “ICT + ESIPT” mechanism for mitochondrial MAO imaging: Distinguishing cells and visualizing DILI

Ting Cao,Mengjin Li,Hong Ma,Zhefeng Fan

A novel AIE-1 probe integrates “ICT + ESIPT+AIE” tri-modal for ratiometric NIR fluorescence imaging of MAO activity. • AIE-1 exhibits wide linear range (0–140 μg/mL), high sensitivity (LOD 0.23 μg/mL), and excellent selectivity. • AIE-1 semi-quantitatively distinguishes MAO activity in normal/cancer cells and evaluates cellular inhibitor efficacy. • Successful real-time visualization of upregulated MAO activity is achieved in a DILI model. Given the crucial role of monoamine oxidase (MAO) in maintaining amine homeostasis and liver pathology, real-time in situ monitoring of its activity is crucial for elucidating the mechanism of drug-induced liver injury (DILI). This study designed and synthesized a ratio type fluorescent probe AIE-1 based on the “ICT + ESIPT” mechanism, which integrates aggregation induced luminescence (AIE), near-infrared (NIR) emission, and mitochondrial targeting. The probe AIE-1 utilizes MAO catalyzed oxidative deamination reaction to trigger intramolecular charge transfer and excited state proton transfer processes, producing significant ratiometric fluorescence signals at 518 nm and 712 nm. The sensing mechanism was thoroughly validated by 1 H NMR titration, DFT calculations of HOMO-LUMO energy gaps, and solvent-polarity-dependent experiments, collectively confirming the occurrence of both ICT and ESIPT processes. Spectral experiments show that its detection of MAO has a wide linear range (0–140 μg/mL), high sensitivity (0.23 μg/mL), strong selectivity, and anti-interference ability. Cell imaging experiments have confirmed that AIE-1 can successfully semi quantitatively distinguish the differences in MAOs activity between normal liver cells and liver cancer cells, and evaluate the effectiveness of inhibitors. In the drug-induced liver injury model, AIE-1 successfully achieved real-time visualization monitoring of upregulation of MAO activity in vivo with sensitivity and specificity. This probe provides a novel and efficient tool for studying the role of MAO in pathological processes such as DILI.

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TALANTA · 2017 · IF 4.162

A new strategy for fabrication of water dispersible and biodegradable fluorescent organic nanoparticles with AIE and ESIPT characteristics and their utilization for bioimaging

Dazhuang Xu,Meiying Liu,Hui Zou,Jianwen Tian,Hongye Huang,Qing Wan,Yanfeng Dai,Yuanqing Wen,Xiaoyong Zhang,Yen Wei

Fluorescence probes play a crucial role in optical imaging for visualization of complex biological processes. As compared with conventional organic fluorogens , the probes with aggregation-induced emission (AIE) and excited-state intramolecular proton transfer (ESIPT) characteristics show significant advantages in high quantum yield at concentrated and aggregated state, large Stokes shift and low cytotoxicity. However, the synthesis of AIE-active fluorescent probes through the ESIPT mechanism has received only very limited attention. On the other hand, the preparation of biodegradable fluorescent probes through the ESIPT mechanism has not been demonstrated thus far. In this work, we reported for the first time that water dispersible and biodegradable fluorescent polymeric nanoparticles with AIE and ESIPT characteristics could be facilely obtained through conjugation of 2,4-Dihydroxybenzophenone based benzophenone azine (BPA) and polyethylene glycol (PEG) using hexamethylene diisocyanate . The final copolymers contained hydrophilic and biocompatible PEG and biodegradable urethane linkage are readily self-assembled into core-shell nanostructures . Moreover, the self-assembled BPA-PEG 2000 fluorescent organic nanoparticles (FONs) displayed obvious AIE feature, high water dispersibility, superb biocompatibility, biodegradability and excellent cell dyeing performance. All of the above properties implied that BPA-PEG 2000 FONs are promising candidates for a variety of biomedical applications.

研究领域: 材料科学 · 生物医学工程 · 光学成像
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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

A water-soluble fluorescent probe derived from fish collagen peptides for multi-targeted detection of Cu2+ and Zn2+ ions via AIE and ESIPT mechanisms

Wenyu Guo,Yuanyuan Zhang,Yunxuan Wang,Zhijun Hu,Peixuan Xu,Jingying Cai,Peirong Yu,Shiya Chen,Lei Zhang,Benmei Wei,Juntao Zhang,Sheng Li,Haibo Wang,Lingyun Chen

Peptides, which are hydrolysis products of proteins, are commonly utilized as nutritional supplements in food due to their high bio-safety profile. In this study, we present a novel water-soluble fluorescent probe derived from fish collagen peptides, termed Sali-Pep. This probe exhibits light green fluorescence, characterized by both aggregate-induced-emission (AIE) and excited state intramolecular proton transfer (ESIPT) mechanisms, with emission peaks at 480 nm and 522 nm. Furthermore, Sali-Pep demonstrates a high sensitivity towards Cu 2+ ions via a “turn-off” fluorescence mechanism, and towards Zn 2+ ions through a “turn-on” fluorescence mechanism, both in a dose-dependent manner. The detection limits of Sali-Pep were 1.49 × 10 −7  M for Cu 2+ and 4.23 × 10 −7  M for Zn 2+ , respectively. In real environmental and biological samples, the recoveries of Cu 2+ and Zn 2+ ions ranged from 91.14 % to 108.61 %. These findings indicate that Sali-Pep is a promising fluorescent probe for the detection of Cu 2+ and Zn 2+ ions, combining both high biosafety and low environmental risk. Additionally, this study also show that collagen-derived peptides have the potential to serve as AIE sensing platforms for metal ion detection and fluorescent labeling.

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ANALYST · 2011 ·Vol. 136 ·期 21 ·4480-4485 · IF 3.913

Fluorescence light-up recognition of DNA nucleotide based on selective abasic site binding of an excited-state intramolecular proton transfer probe

Shujuan Xu,Yong Shao,Kun Ma,Qinghua Cui,Guiying Liu,Fei Wu,Minjie Li

DNA single-nucleotide polymorphism (SNP) detection has attracted much attention due to mutation-related diseases. Various fluorescence methods for SNP detection have been proposed and many are already in use. However, fluorescence enhancement for signal-on SNP identification without label modification still remains a challenge. Here, we find that the abasic site (AP site) in a DNA duplex can be developed as a binding pocket favorable for the occurrence of the excited-state intramolecular proton transfer (ESIPT) of a 3-hydroxyflavone, fisetin, which is used as a proof of concept for effective SNP identification. Fisetin binding at the AP site is highly selective for target thymine or cytosine facing the AP site by observation of a drastic increase in the ESIPT emission band. In addition, the target recognition selectivity based on this ESIPT process is not affected by flanking bases of the AP site. The binding selectivity of fisetin at the AP site is also confirmed by measurements of fluorescence resonance energy transfer, emission lifetime and DNA melting. The fluorescent signal-on sensing for SNP based on this fluorophore is substantially advantageous over the previously used fluorophores such as the AP site-specific signal-off organic ligands with a similar fluorescing mechanism before and after binding to DNA with hydrogen bonding interaction. We expect that this approach will be employed to develop a practical SNP detection method by locating an AP site toward a target and employing an ESIPT probe as readout.

CAS / MDL: 528-48-3
研究领域: 化学 · 生物化学 · 分子生物学 · 遗传学
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Ortho-Vanillin-based fluorescent sensor with ESIPT characteristics for selective detection of Al(III) in aqueous solutions and its application for plant and live-cell imaging

Yongjie Ding,Chunxiang Zhao,Pengcheng Zhang,Yali Cui,Yahong Chen,Jianping Xie,Weiwu Song,Zengchen Liu,Yongliang Ban,Ge Liu,Juan Yang

A new acylhydrazone fluorescent sensor ( VN62 ) with excited intramolecular proton transfer (ESIPT) characteristics has been designed and synthesized through condensation of o -vanillin with 6‑hydroxy-2-naphthoic hydrazide for selective detection of Al 3+ in aqueous medium. The structure of the VN62 sensor was characterized by various techniques such as 1 H and 13 C NMR and mass spectrometry, and also confirmed by single crystal X-ray diffraction. The VN62 sensor showed a remarkable fluorescence enhancement response to Al 3+ over a broad pH range in a nearly 100 % aqueous solution without interference by most of tested metal ions and anions. Through fluorescence titration and a Job's plot experiment, the binding stoichiometry of VN62 with Al 3+ was found to be 1:1. The limit of detection of VN62 toward Al 3+ was determined as 39.6 nM and the binding constant was 2.66 × 10 4  M −1 . Comprehensive analyses by HR-MS, 1 H NMR and density functional theory calculations illustrated that the VN62 sensor coordinated with Al 3+ , forming a stable trigonal bipyramid structure complex, which blocked the ESIPT and photoinduced electron transfer processes and simultaneously promoted an intramolecular charge transfer process, thereby leading to strong cyan fluorescence. Moreover, VN62 -loaded test strips were successfully applied for rapid and visual detection of Al 3+ . Furthermore, the VN62 sensor was used to visualize Al 3+ in plants and live cells. The results indicated that the VN62 sensor has great potential for detecting Al 3+ in biological systems.

CAS / MDL: 148-53-8
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Journal of Materials Chemistry C · 2023 ·Vol. 11 ·期 27 ·9252-9261 · IF 6.4

Synthesis and characterization of a large Stokes-shifted fluorescent imide and its related polyimides bearing 2-(2′-hydroxyphenyl)benzothiazole moieties

Yuehong Luo,Kaijin Chen,Wenhui Wang,Ruxin Bei,Chuying Li,Yubo Long,Zhuxin Zhou,Siwei Liu,Zhenguo Chi,Jiarui Xu,Yi Zhang

A large Stokes-shifted fluorescent imide (HBTN-MC) and its related polyimides (HBHBTNms and HPHBTNms) were first designed and synthesized by introducing an excited state intramolecular proton transfer fluorophore 2-(2′-hydroxyphenyl)benzothiazole (HBT). The imide exhibited a large Stokes shift of 9654 cm−1 in the dichloromethane solution and 7648 cm−1 in the solid state. Based on the experimental and theoretical methods, the photophysical properties and the excited state intramolecular proton transfer (ESIPT) process of HBTN-MC have been systematically studied. The performances of the polyimides have been optimized by changing the alicyclic dianhydride and adjusting the copolymerization ratio. The as-prepared polyimide films retained the ESIPT performance with a large Stokes shift of larger than 8105 cm−1, a high photoluminescence quantum efficiency (φ) of 29%, decent colorless and transparency, high thermal performance (Td, 5% = 468 °C and Tg > 260 °C), and solubility in both conventional aprotic and protic solvents. In short, the newly developed imide and polyimides provide good examples for the development of ESIPT polymers with controllable emission wavelengths as well as high thermal, environmental, and radiation stability.

研究领域: 材料科学 · 聚合物化学 · 光学材料 · 荧光材料
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CHEMICAL ENGINEERING JOURNAL · 2023 · IF 15.1

Excited-state intramolecular proton transfer emitter for efficient violet-blue organic light-emitting diodes with hybridized local/charge transfer channel

Yibing Wu,Rongxin Wang,Rui Lin,Xuee Xu,Xingye Zhang,Osamah Alsalman,Yu Qiu,Ashraf Uddin,Xinhua Ouyang

Excited-state intramolecular proton transfer (ESIPT) materials have attracted much interest, attributed to their metastable excited states which provide suitable platforms for efficient intersystem crossing (ISC) and reverse intersystem crossing (rISC). However, the studies on the utilization of ESIPT to achieve effective hybridized local/charge transfer (HLCT) emitters are rarely reported, due to their ubiquitous issue of low photoluminescence quantum yields (Φ PLs ). In this research, a novel ESIPT molecule with HLCT characteristic, 4′-(diphenylamino)-4-(1,4,5- triphenyl-1H-imidazol-2-yl)-[1,1′-biphenyl]-3-ol (HIT-TPA), is designed and synthesized. The hydrogen atom in this molecule can transfer on the way of an intramolecular hydrogen bond from a proton-donating part (–OH/–NH–) to the accepting one (C O/C N–). The HLCT and /or color-tuned fluorescence are observed by the irradiation of specific wavelength, which followed the guidance of ESIPT. It is consistent with the results of transient absorption and time-resolved photoluminescent spectroscopy. By the synergistic interaction of ESIPT and HLCT, the film based on the target molecule presents a high Φ PL value of ∼75.5%. After employing HIT-TPA as the emitter for doped/undoped organic light-emitting diodes (OLEDs), a maximum external quantum efficiency of ∼10.08% is achieved, which proves the efficient triplet harvesting in the ESIPT-based HLCT material. Noticeably, the device exhibits a violet-blue emission with the CIE(x,y) of (0.152, 0.051). It is among the highest reported EQE values on the ESIPT-HLCT materials for violet-blue devices. These results not only open a novel pathway to design effective ESIPT attributed HLCT materials, but also provide a strategy to efficiently utilize ESIPT emitters in achieving high-performance OLEDs.

研究领域: 材料科学 · 光电学 · 有机电子学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Highly selective and sensitive turn-on fluorescent probes for sensing Hg2+ ions in mixed aqueous solution

Zhen-Long Wu,Di Shi,Li Huang,Wen-Ying He,Xiang-Ying Sun,Bin Liu,Jiang-Shan Shen

A highly selective and sensitive probe 1b was successfully developed for detecting Hg 2+ ions in mixed aqueous medium with a “turn on” fluorescence mode, via a series of structural optimization of probes. These probes could be easily synthesized by one-step condensation reactions between o -phenylenediamine or 2, 3-diaminonaphthalene and o (salicylaldehyde), m , or p- hydroxybenzaldehyde. Introducing a certain amount of Hg 2+ ions the fluorescence of probes bearing one or two salicylaldehyde moieties including probes 1a, 1b, and 4 could be turned on. The fluorescent response is likely due to the well matching between Hg 2+ ions size and the geometric structure of probes, resulting in that probes bearing salicylaldehyde moiety are mostly favorable for binding with Hg 2+ ions by way of 1:1 molar ratio. These bindings likely facilitate excited state internal proton transfer (ESIPT) or ESIPT coupled aggregation-induced enhancement of emission (AIEE) process. Considering the sensitivity and the potential of practical application, probe 1b was chosen to establish a fluorescent enhancement sensing system towards Hg 2+ ions over other competing metal ions, with excellent limit of detection of 12.5 ppb.

研究领域: 分析化学 · 环境科学 · 材料科学
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