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ESIPT
RSC Advances · 2018 ·Vol. 8 ·期 57 ·32497-32505 · IF 2.936

A “Turn-On” fluorescent probe for sensitive and selective detection of fluoride ions based on aggregation-induced emission

Man Du,Baolong Huo,Mengwen Li,Ao Shen,Xue Bai,Yaru Lai,Jiemin Liu,Yunxu Yang

Based on the fluorophore of 2-(2′-hydroxyphenyl)benzothiazole (HBT) with aggregation-induced emission (AIE) properties, a highly selective and sensitive fluorescent probe PBT towards F− was investigated. “Turn-On” fluorescence type signaling was realized by employing fluoride-selective cleavage of the latent thiophosphinated probe in mixed aqueous media. The probe is designed in such a way that the excited state intramolecular proton transfer (ESIPT) of the HBT moiety becomes blocked. The chemodosimetric approach of F− to the probe results in the recovery of the ESIPT by removal of a free AIE-active HBT moiety through a subsequent hydrolysis process. The F− detection limit of the probe was 3.8 nM in the dynamic range of 0.5 μM to 10 μM. In addition, the proposed probe has been used to detect F− in water samples and toothpaste samples with satisfying results.

研究领域: 分析化学 · 环境科学 · 材料科学
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MOLECULAR PHYSICS · 2024 · IF 1.6

Ultrafast dual-fluorescence dynamics of 2-(2'-hydroxyphenyl) benzimidazole by femtosecond transient absorption spectroscopy

Gang Wang,Lina Ding,Yang Liu,Yonggang Yang,Yufang Liu

2-(2'-Hydroxyphenyl) benzimidazole (HBI) and its derivatives are widely used in fluorescent probes, luminescent materials, and other sensing materials. In this study, the time-resolved fluorescence behaviour, and excited-state dynamics of HBI and 2-phenyl-1H-benzo[d]imidazole (BI) were studied using femtosecond transient absorption (fs-TA) spectroscopy. The stimulated emission (SE) and excited-state absorption signals of the BI molecule were located at 355 and 437 nm, respectively. For HBI, these signals were located at 475 and 384 nm, respectively. The SE signals of the BI and HBI molecules in their fs-TA spectra were consistent with the experimental short-wave fluorescence at 340 and 460 nm, respectively, in the steady-state spectra. The long-wave signal of HBI at 475 nm indicates its dual fluorescence, which may be caused by proton transfer or conformational torsion after photoexcitation. The large theoretical energy barrier of 40.97 kcal/mol in first excited (S1) state of HBI excludes the latter hypothesis. Additionally, the small energy barrier (1.88 kcal/mol) in the S1 state confirmed the excited-state intramolecular proton transfer (ESIPT). This indicates that ESIPT induces dual fluorescence behaviour of the HBI molecule, which was also demonstrated by the infrared spectra, theoretical fluorescence peaks, and molecular orbitals.

研究领域: 光化学 · 物理化学 · 理论化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

Probe with large Stokes shift for effective cysteine imaging in living cells

Fengxia Zou,Chun Wang,Wenwu Song,Lujie Shen,Runsheng Xu,Miao Wang,Minmin Wang,Tongming Sun,Jin Wang

A new fluorescence probe L , which featured with a large Stokes shift (216 nm), was designed for sensitive detection of cysteine (Cys) and a potential sensing mechanism derived from excited state intramolecular proton transfer (ESIPT) was proposed. More importantly, probe L exhibits higher selective to Cys than other amino acid due to its specific cyclization between acrylate group and Cys. Meanwhile, the probe L shows a low detection limit of 8.82 × 10 −8 M, which is enough for detecting Cys in organisms. Furthermore, this probe displays high biocompatibility and can image Cys in living cells.

研究领域: 生物化学 · 分子生物学 · 分析化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2017 · IF 2.536

A highly selective and sensitive turn-on probe for aluminum(III) based on quinoline Schiff's base and its cell imaging

Fenfen Zhou,Hongqing Wang,Pengying Liu,Qinghua Hu,Yuyuan Wang,Can Liu,Jiangke Hu

A reversible Schiff's base fluorescence probe for Al 3+ , (3,5-dichloro-2- hydroxybenzylidene) quinoline-2-carbohydrazide ( QC ), based on quinoline derivative has been designed, synthesized and evaluated. The QC exhibited a high sensitivity and selectivity toward Al 3+ in EtOH-H 2 O (v/v   =   1:9, pH   =   6) by forming a 1:1 complex with Al 3+ and the detection limit of QC for Al 3+ was as low as 0.012   μM. Furthermore, these results displayed that the binding of QC Al 3+ was broken by F − , so this system could be used to monitor F − in the future. The enhancement fluorescence of the QC could be attributed to the inhibition of PET and ESIPT and the emergency of CHEF process induced by Al 3+ . More importantly, QC was not only successfully used for the determination of trace Al 3+ in the tap water and the human blood serum, but was valid for fluorescence imaging of Al 3+ in the Hela cells.

研究领域: 分析化学 · 生物医学
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CHEMICAL PHYSICS LETTERS · 2026 · IF 3.1

Effects of substituents and solvent polarity on ESIPT and antioxidant activity of 2,6-Dihydroxybenzaldehyde

Haoran Ma,Yongchun Li,Nan Yang,Siyi Wang,Xiatiguli Kahaer,Mei Xiang,Bumaliya Abulimiti,Xiaoning Wang

2,6-Dihydroxybenzaldehyde (2,6-DHBA), featuring ortho phenolic hydroxyl groups, exhibits notable antioxidant properties. However, the influence of substituents and solvent polarity on its ESIPT behavior and radical scavenging ability remains unclear. Using DFT and TD-DFT methods, we systematically investigated how electron withdrawing (-CN) and electron donating (−NH 2 ) groups, together with dichloromethane and dimethyl sulfoxide solvents, regulate ESIPT and antioxidant activity. The -CN group promotes ESIPT but weakens antioxidant activity, whereas -NH 2 shows the opposite effect. Lower solvent polarity favors ESIPT. These findings provide theoretical guidance for designing phenolic antioxidants and functionalized ligands.

CAS / MDL: 387-46-2 67-68-5
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SENSORS AND ACTUATORS B-CHEMICAL · 2026 · IF 8.3

Independent rotation design on ESIPT-scaffold for precise fluorescence modulation and trace hydrazine sensing

Yali Feng,Luyan Yang,Yingxing Li,Chuanfang Zhao,Xincun Dou,Baiyi Zu

Hydrazine (N 2 H 4 ) is a highly toxic and carcinogenic chemical extensively used in pharmaceutical manufacturing, agrochemicals, and aerospace industries, posing significant threats to environmental safety and human health due to its persistence and volatility. Consequently, the development of reliable methods for trace-level detection of hydrazine in both aqueous and gaseous environments is urgently needed. Here, we report a fluorescence turn-on probe based on an excited-state intramolecular proton transfer (ESIPT) platform, employing a unique rotation-induced complete energy dissipation strategy with the advantage of effective conversion between the turn-on/off mode. The probe is rationally designed by embedding the dual isolated rotors onto the ESIPT-scaffold, which introduces substantial rotation freedom in molecules and large dihedral angular distortion, resulting in the dissipation of the original radiative transition and the Emission-OFF state. Upon the specific binding of analyte and the reactive rotor, the rigid hexagonal ring could efficiently form and the π-conjugation plane could further expand, leading to the disruption of ESIPT and the Emission-ON state. This mechanism enables efficient switching from a non-emissive to a highly emissive state with near-zero background interference. Thus, a boosted turn-on detection towards trace hydrazine was achieved in both aqueous and vapor phases with theoretical limit of detection (LOD) of 11.64 nM and 26 ppb, as well as desirable anti-interference capability against 18 soluble and 11 volatile substances, respectively. The present strategy is expected to greatly expand the near-zero background fluorescence turn-on molecular design strategies and open avenues for high-performance volatile threats sensing.

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JOURNAL OF MOLECULAR LIQUIDS · 2025 · IF 5.2

ESIPT mechanism and multi-stimuli-responsive of N-phenylanthranilic acid under AIE characteristics in solution

Jiaqi Luo,Yingchen Wang,Qiutong Zhang,Wenhao Yan,Yimin Jia,Mingting Yuan,Qiushuo Yu,Xinyue Zhai,Yuan Zou

N -phenylanthranilic acid (NPAA) is weakly acidic compound that exhibits both excited-state intramolecular proton transfer (ESIPT) and aggregation-induced emission (AIE) characteristics. The molecular structure was confirmed, and its optical behavior was rationalized through a combined approach of quantum chemical calculations and experimental studies. At low concentrations in various solvents, NPAA exhibits dual emission, indicative of an ESIPT process. At higher concentrations, self-association leads to the formation of dimers, resulting in a single emission peak in the fluorescence spectrum. The emission intensity significantly increases with an increasing water fraction in methanol/H 2 O mixtures, demonstrating typical AIE behavior. Additionally, NPAA exhibits time-dependent enhancement of blue-shifted emission and pH-dependent fluorescence responses. Upon adding a large amount of water to the methanol solution (up to about 70 % water fraction), the mixture shows a gradual enhancement accompanied by a blue shift in fluorescence emission. Under alkaline conditions, the carboxyl group becomes negatively charged, which increases intermolecular electrostatic repulsion and weakens hydrogen bonding interactions. As a result, molecular aggregation is inhibited, leading to fluorescence quenching. In contrast, under acidic conditions, the molecules aggregate more readily, which enhances fluorescence emission, and the crystal morphology changes from needle-like to sheet-like. NPAA thus exhibits reversible acid-base responsive fluorescence switching behavior. Furthermore, NPAA films enable reversible fluorescence switching under acid/base vapor stimuli, demonstrating its potential in vapor-responsive luminescent sensing.

CAS / MDL: 1336-21-6 91-40-7
研究领域: 光化学 · 材料科学 · 发光传感器 · 有机电子学 · 超分子化学
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RSC Advances · 2015 ·Vol. 5 ·期 93 ·76296-76301 · IF 3.84

Proton donor modulating ESIPT-based fluorescent probes for highly sensitive and selective detection of Cu2+

Liyan Huang,Biao Gu,Wei Su,Peng yin,Haitao Li

Two novel ESIPT-based fluorescent probes, N-(2-(1-(p-tolyl)-1H-phenenanthro[9,10-d]imidazol-2-yl)phenyl) picolinamide (Pi-A) and 2-(1-(p-tolyl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenylpicolinate (Pi-E), were designed and synthesized. The favorable features of the proposed probes included excellent water solubility, wide pH range, high selectivity and sensitivity to Cu2+. Interestingly, the difference in the linker of the probe molecules led to a radical change in the fluorescent response of the probes to Cu2+. Pi-A showed fluorescence turn-off towards Cu2+ with a detection limit of 1.6 × 10−9 M and Pi-E showed fluorescence turn-on towards Cu2+ with a detection limit of 1.8 × 10−8 M in the same condition. The Cu2+ recognition mechanisms of the probes were investigated by Job's plot analyses, NMR and ESI-MS spectroscopy experiments. Moreover, our experiments also showed that the probes are of excellent cell permeability and are capable of imaging Cu2+ within living cells.

研究领域: 分析化学 · 传感器与探针 · 无机化学 · 生物成像
✓ 已验证 DOI 高影响因子
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ANALYTICA CHIMICA ACTA · 2023 · IF 6.2

A susceptible coordination hybrid based terbium sensibilization coupled ESIPT effects for pattern discrimination of analogues

Shengdi Tai,Sichen Li,Ruijie Zheng,Yan Huang,Kang Yang,Shishen Zhang,Jiadan Xue,Benxia Li,Kun Zhang

Multianalyte detection and analogue discrimination are extremely valuable frontier areas for their wide applications in environmental, medical, clinical and industrial analyses. Nowadays, researchers rack their brains on how to develop excellent multianalyte chemosensors that have presented huge challenges in designing high-efficient fluorescent sensing materials and constructing high-throughput detection methods. In this paper, we propose a novel strategy to utilize the dual-emission fluorescent detection platform as a lab-on-a-molecule, arising from the disalicylaldehyde-coordinated hybrid H 2 Q j3 /Tb based terbium sensibilization coupled excited-state intramolecular proton transfer effects. Using the statistical analysis (PCA and HCA) for sensing signals of three fluorescence channels (431, 543 and 583 nm), we demonstrate this elaborate chemosensor with multianalyte detection of three species (solvents, anions and cations) and pattern discrimination of analogues. As a result, the H 2 Q j3 /Tb shows great lab-on-a-molecule characters for each set of species, resulting in the easier identification of many critical analytes (e.g., H 2 O, NO 2 − and Fe 3+ ) and discrimination of analogues. In addition, it is also proven to be able to provide reliable content determination for an analyte, especially the NO 2 − (LOD = 0.37 μM), and discrimination for mixed analogues. A combination of easy-to-implement preparation procedure and data analysis technique makes this work promising for not only designing similar lanthanide-based materials but also realizing more high-efficient multianalyte sensing systems towards various potential applications.

研究领域: 化学传感 · 材料科学 · 环境分析
✓ 已验证 DOI PubMed 高影响因子
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2026 · IF 4.1

An ICT + ESIPT synergistic NIR ratiometric probe for mitochondrial MAOs imaging in vivo and in vitro

Cao Ting,Li Mengjin,Ma Hong,Fan Zhefeng

The liver is a vital metabolic and detoxification organ in the body, yet the diagnosis of drug-induced liver injury (DILI) remains challenging due to the limitations of traditional detection methods. Monoamine oxidases (MAOs), which are highly expressed on the mitochondrial membrane of hepatic tissues, are closely associated with DILI. In this study, a near-infrared ratiometric fluorescent probe Mito-1 was developed based on the intramolecular charge transfer (ICT) and excited-state intramolecular proton transfer (ESIPT) mechanisms. This probe could precisely target mitochondria, exhibiting high sensitivity (DL = 0.14 μg/mL), a wide linear detection range (10–150 μg/mL), excellent selectivity towards MAOs, and good biocompatibility. Cellular experiments confirmed its ability to distinguish MAO activity between normal and liver cancer cells. In an acetaminophen (APAP)-induced DILI zebrafish model, Mito-1 enabled in vivo dynamic visualization of MAO activity in hepatic tissues. Collectively, this work provides a novel visual tool for the early diagnosis of DILI and the mechanistic study of MAOs. Graphical The alternative text for this image may have been generated using AI.

✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF MOLECULAR STRUCTURE · 2025 · IF 4.7

A HBT-based multifunctional ratiometric fluorescence probe for naked-eye sensing pH and fluoride

Meili Yang,Liu Yang,Huixin Yu,Xin Zhang,Zhong Zhang,Mao-Sen Yuan

Based on the ESIPT effect, a fluorescence probe HBT-TBD was successfully synthesized, with HBT as the luminescent group and a Si-O bond as the F - recognition site. HBT-TBD is a typical ratiometric fluorescence probe, and can realize the naked-eye monitoring of F - quickly and sensitively. HBT-TBD exhibits different fluorescence colour at various pH, providing a promising approach for developing a new type of acid-base indicator.

研究领域: 分析化学 · 生物传感器 · 分子探针 · 荧光成像 · 环境监测 · 临床诊断
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2026 · IF 4.8

Communication of bifunctional G-quadruplex chaperone with aptamer for highly selective adenosine signaling by an ESIPT fluorogen

Qiyao Chen,Sihui Huang,Jiahuan Zhou,Jiahui Chen,Dandan Wang,Qingqing Zhang,Xiaoshun Zhou,Yong Shao

Adenosine (Ade) is an important bioactive molecule in energy metabolism, signaling, immune regulation, and cardiovascular protection, etc. Ade in serums during ischemic episode can abnormally reach to a few to tens of μM from the normal nM level. The currently developed aptamer methods for Ade and adenylate are widely used as the straightforward and cascade biosensing models. However, an ideal label-free method with high Ade-over-adenylate selectivity, turn-on fluorescence even at a few of μM level, and reference correction from sample matrix fluctuation has not yet been elucidated. Herein, we found that duplex can communicate with a G-quadruplex (G4) chaperone to light up the green tautomer fluorescence of 3-hydroxyflavone based on the excited state intramolecular proton transfer (ESIPT) process, while the normal blue reference emission at shorter wavelength is not affected. Accordingly, engineering the duplex with a newly screened aptamer also succeeded in favoring the ESIPT emission via responding to Ade, while the densely packed negative charge density in the G4 chaperone inhibited adenylate association with the aptamer. Therefore, the G4 chaperone is bifunctional. The aptamer-G4 ensemble was effectively applied to the serum analysis without any interference from the serum matrix. The specificity of aptamer-G4 ensemble towards Ade was also confirmed by adenosine deaminase (ADA), which was able to monitor the Ade dynamics and the ADA activity. It is expected that our method could be applied to other aptamers by chaperoning an appropriate G4 structure.

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