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ESIPT
Analytical Methods · 2015 ·Vol. 7 ·期 9 ·3883-3887 · IF 1.821

An ESIPT-based ratiometric fluorescent probe for the imaging of nitroxyl in living cells

Hao-Ming Lv,Yi Chen,Jian Lei,Chak-Tong Au,Shuang-Feng Yin

Nitroxyl is a highly reactive compound that irreversibly dimerizes and subsequently dehydrates to yield nitrous oxide and water, making its direct detection in cells or in vivo difficult. In this paper, a novel fluorescent probe 1 based on the excited state intramolecular proton transfer (ESIPT) mechanism for the detection of nitroxyl was developed for the first time. It consists of 2-(2′-hydroxyphenyl)-benzothiazole as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group. The probe exhibited high sensitivity and selectivity toward nitroxyl in the presence of biologically relevant species. Moreover, the potential for biological applications of the probe was confirmed by employing it for fluorescence imaging of nitroxyl in living cells.

研究领域: 生物化学 · 分析化学 · 细胞生物学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

A benzothiazole-rhodol based luminophor: ESIPT-induced AIE and an application for detecting Fe2+ ion

Jianping Guan,Qin Tu,Long Chen,Mao-Sen Yuan,Jinyi Wang

Herein, we designed and synthesized a luminophor, Rh-F , which is an intergrant of rhodol and 2-hydroxy benzothiazole by introducing a benzothiazole unit onto the ortho-position of the phenolic hydroxy of rhodol. Rh-F exhibited excellent fluorescence properties such as a large Stokes shift (>180 nm) and the synergistic effect of aggregation-induced emission (AIE) and an excited state intramolecular proton transfer (ESIPT) feature. The AIE/ESIPT mechanism was thoroughly explored using X-ray single-crystal structures and photophysical determinations. Furthermore, Rh-F showed a sensitive fluorescence response to Fe 2+ with low detection limits of 115.2 nM and high selectivity. Studies of its sensing mechanism indicated that the Fe 2+ -induced blue-green fluorescence-quenched at 525 nm originates from an irreversible Fe 2 + chelate with the oxygen atom of the hydroxyl group and the N atom of the benzothiazole moiety. This blocked the ESIPT process of Rh-F which resulted in the quenching of the fluorescence sensor for Rh-F .

研究领域: 化学 · 材料科学 · 分析化学
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ANALYTICAL CHEMISTRY · 2023 · IF 7.4

Precise Electron-Withdrawing Strength Modulation of ESIPT Probes for Ultrasensitive and Specific Fluorescence Sensing

Yanwen Guo,Zhenzhen Cai,Fei Yan,Da Lei,Yanan Guo,Shuhai Zhang,Xincun Dou

The precise regulation of the electron-withdrawing/electron-donating strength in a probe is of great significance for the design of reaction-based fluorescent probes with specific functionalities. Here, a family of excited-state intramolecular proton transfer (ESIPT)-based probes with fluorescence turn-on sensing properties toward KMnO4 was designed by precisely modulating the electron-withdrawing strength of the substituents located at the para-position of the recognition group. It is found that −F, −CHO, and −H as the electron-withdrawing groups bound at the probe can specifically recognize KMnO4, which ensures a blue emission displayed by the reaction products. Especially with −CHO as the electron-withdrawing group, the reaction product shows the most stable fluorescence. The probe 2-(benzo[d]oxazol-2-yl)-4-formylphenyl acrylate (BOPA-CHO) demonstrated a more superior sensing performance toward KMnO4, including a low limit of detection (LOD, 0.96 nM), a rapid response (<3 s), and a rather good selectivity even in the presence of 21 interferents. Moreover, the practicality of the probe was further verified by a test pen comprising a BOPA-CHO-embedded sponge, which is capable of detecting KMnO4 solid with a naked-eye LOD of 11.62 ng. The present probe design and modulation strategy would open up a new path for the design of high-performance fluorescent probes.

研究领域: 分析化学 · 荧光传感 · 材料科学
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RESEARCH ON CHEMICAL INTERMEDIATES · 2017 ·Vol. 44 ·期 1 ·491-502 · IF 1.369

A off–on pH fluorescence probe derived from phenanthro[9,10-d]imidazol-fluorescein based on ESIPT and ICT

Li Shaoxin,Zhao Bing,Kan Wei,Wang Liyan,Song Bo,Chen Shuwen

A novel pH fluorescence probe (PIF), derived from phenanthro[9,10- d ]imidazole bound to the fluorescein, is designed and synthesized based on the intramolecular hydrogen bond and then its spectra properties are investigated. Probe PIF exhibits negligible fluorescence intensity at acidic pH condition due to ESIPT quenching caused by the formation of the intramolecular hydrogen bonds, and a significant fluorescence enhancement in neutral and weak alkaline environments because of the strengthened ICT process arose from the fracture of the intramolecular hydrogen bonds. The studies of UV–Vis and fluorescence spectra mean that probe PIF is able to respond linearly and reversibly over pH from 6.5 to 9.0 with p K a of 7.0. Moreover, the pH responses of probe PIF are stable and not disturbed by the common cations and anions. The possible response mechanism has been proposed according to the analysis of 1 H NMR and DFT calculations.

研究领域: 分析化学 · 生物化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

ESIPT-based fluorescent enhanced probes prompted by methylated β-cyclodextrin for the detection of thiophenols

Hai-Yan Peng,Gang Zhang,Ru Sun,Yu-Jie Xu,Jian-Feng Ge

Thiophenol and its derivatives are compounds with high toxicity to organisms and environmental pollution, so it is necessary to detect the level of thiophenols in the environment and biological samples. The probes 1a-b were obtained by introducing the 2,4-dinitrophenyl ether group into diethylcoumarin–salicylaldehyde based compounds. And they can form host-guest compounds with methylated β-cyclodextrin (M-β-CD), the association constants of inclusion complexes are 49.2 M −1 , 125 M −1 respectively. The fluorescence intensities of probes 1a-b at 600 nm ( 1a ) and 670 nm ( 1b ) increased significantly in thiophenols detection. Meanwhile, with the addition of M-β-CD, the hydrophobic cavity of M-β-CD significantly increased the fluorescence intensity of probes 1a-b , thus the detection limits of probes 1a-b to thiophenols were reduced from 410 nM, 365 nM to 62 nM, 33 nM respectively. Whereas, the good selectivity and short response time of probes 1a-b towards thiophenols was not affected in the presence of M-β-CD. Moreover, probes 1a-b were used for further water sample detection and HeLa cell imaging experiments due to their good response to thiophenols and the results suggested that probes 1a-b had the potential to detect the content of thiophenols in water samples and living cells.

CAS / MDL: 67-64-1
研究领域: 分析化学 · 环境科学 · 生物医学
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POLYHEDRON · 2020 · IF 2.343

A bifunctional optical probe based on ESIPT-triggered disalicylaldehyde with ratiometric detection of iron and copper ions

Yin-Jing Shen,Kun Zhang

In this paper, we design and synthesize an N -linked disalicylaldehyde H 2 Q j1 based on the economical substrates, and it is composed of two identical salicylaldehyde moieties with the intramolecular ESIPT character. During the process of sensing heavy metal ions, it is found that the ESIPT state of H 2 Q j1 can be rapidly (60 s) destroyed by Fe(III) and Cu(II), resulting in the turn-off fluormetric and colorimetric responses. Serial fluorescence and absorption titration experiments reveal that the H 2 Q j1 -Fe(III) and H 2 Q j1 -Cu(II) sensing systems are ratiometric and their corresponding coordination modes are 1:1 and 2:1. Especially, their LOD values are as low as 0.40 μΜ and 0.21 μΜ which are comparable to reported examples. Moreover, we also develop a convenient technique to detect Fe(III) and Cu(II) using paper-based sensing devices together with smartphone-based RGB analysis method which will rapidly provide the precise determination results, even in the tap water sample. Therefore, this bifunctional disalicylaldehyde H 2 Q j1 is taken as a useable platform to monitor Fe(III) and Cu(II) and offers some valuable lights for further optical probes.

CAS / MDL: 67-64-1
研究领域: 分析化学 · 光学传感
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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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DYES AND PIGMENTS · 2017 · IF 3.473

Highly sensitive and selective ESIPT-based fluorescent probes for detection of Pd2+ with large Stocks shifts

Tiantian Chen,Tingwen Wei,Zhijie Zhang,Yahui Chen,Jian Qiang,Fang Wang,Xiaoqiang Chen

Highly sensitive and selective fluorescent probes 1 and 2 for detection of palladium ions (Pd 2+ ) were synthesized based on excited-state intramolecular proton transfer process (ESIPT) using 2-(2′-hydroxy-)benzothiazole moiety. Different metal ions were used to optimize their sensitivity and selectivity but best results were obtained with Pd 2+ . Probe 1 produced green fluorescence with Stokes shift of about 163 nm upon addition of Pd 2+ , whereas probe 2 displayed red fluorescence with a large Stokes shift of about 217 nm under similar conditions. The detection limits of 1 and 2 to Pd 2+ were found to be 285 nM and 14.6 nM, respectively. Mechanistic aspects of probes 1 and 2 were discussed to account for the optical changes leading to the strong ESIPT fluorescence in very short duration. Furthermore, the portable test strips were also prepared by direct deposition of the probe molecules onto the filter paper to detect the lowest possible ppm levels of Pd 2+ .

研究领域: 分析化学 · 材料科学
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JOURNAL OF MOLECULAR STRUCTURE · 2020 · IF 2.463

A fluorescent molecular sensor based on ESIPT process for rapid detection of arsenic species in hydrophobic system

Yuxiao Cheng,Shuxin Wang,Jidong Zhang,Jian Cao,Yi Qu

An excited-state intramolecular proton transfer (ESIPT)-based fluorescent sensor (M-HBT) was designed and synthesized and used to detect arsenic species in real naphtha sample. The pH-related emission movement from 610 nm (pH = 1) to 510 nm (pH = 13) evidenced the ESIPT process of M-HBT. The sensing property of M-HBT was investigated in ethanol, and the experimental results provided good linear response of As 3+ in the region of 0–32 μM. A skin contact experiment of M-HBT detecting As 3+ was designed by using the pork sample as a mimic. The naked-eye recognizing emission change of M-HBT was rapidly from yellow to green in 15 s. The fluorescent sensor M-HBT showed the better selectivity towards As 3+ than other cations. The sensing mechanism of M-HBT to As 3+ was verified by 1 H NMR titration spectra.

CAS / MDL: 137-07-5
研究领域: 分析化学 · 环境科学
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DYES AND PIGMENTS · 2016 · IF 4.055

An ESIPT-based fluorescent probe for highly selective detection of glutathione in aqueous solution and living cells

Xintong Ren,Fang Wang,Jing Lv,Tingwen Wei,Wei Zhang,Yong Wang,Xiaoqiang Chen

In this paper, highly sensitive and selective fluorescent probe 1 for GSH is designed and synthesized based on modulation of the excited-state intramolecular proton transfer (ESIPT) process of 2-(2′-hydroxy-3′-ethoxyphenyl)benzothiazole. Upon introducing GSH in neutral solution containing CTAB micelles , dinitrophenyl, the protecting group of the probe, is removed via the nucleophilic substitution , thereby retrieving the ESIPT process of 2-(2′-hydroxy-3′-ethoxyphenyl)benzothiazole, which results in a fluorescence enhancement at 485 nm. Additionally, the fluorescence intensity of the probe is linearly proportional to GSH concentration ranging from 0 to 100 μM and the obtained detection limit is as low as 0.81 μM. The enhanced selectivity toward GSH over Cys and Hcy is also attributed to one more carboxyl group in GSH. Importantly, the probe is successfully utilized for monitoring GSH in living HeLa cells .

CAS / MDL: 137-07-5
研究领域: 生物化学 · 分析化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2022 · IF 9.221

An ESIPT fluorescent probe based on Staudinger reaction for detection of triphenylphosphine and tetrakis(triphenyl-phosphine)palladium

Yuhuan Zhang,Hongjuan Li,Shiguo Sun,Yongqian Xu

Triphenylphosphine (PPh 3 ) and tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) are harmful at extremely low concentration, thus it is essential to explore selective and sensitive method to detect them. Based on Staudinger reaction mechanism, here we present a simple excited-state intramolecular proton transfer (ESIPT) fluorescent probe (HBTN) for detection of PPh 3 and Pd(PPh 3 ) 4 over other phosphine derivatives with differential channel fluorescence (enol and keto emission). The reaction-typed fluorescence probe with novel Staudinger reaction mechanism offers very low autofluorescence and a large signal-to-noise response signal, which is beneficial for the sensitive detection of PPh 3 and Pd(PPh 3 ) 4 . Moreover, HBTN can be used for efficiently detecting Pd(PPh 3 ) 4 residues in highly purified products and imaging PPh 3 in living cells.

研究领域: 分析化学 · 生物医学
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Analytical Methods · 2019 ·Vol. 11 ·期 29 ·3714-3720 · IF 2.378

Polymer nanoparticles integrated with ESIPT modules for sensing cysteine based on modulation of their tautomeric emission

Wu Zou,Qinge Wang,Fuchun Gong,Yinjie Kuang,Jiaoyun Xia,Zhong Cao

Excited-state intramolecular proton transfer (ESIPT)-exhibiting polymer nanoparticles (e-PNPs) were prepared using 2,6-diformyl-4-methylphenol and guanidine hydrochloride. The e-PNPs bear abundant aromatic o-OH, CN and NH2 groups which are responsible for ESIPT modules. By incorporating ESIPT units into nanostructures, the ESIPT moieties can achieve an appropriate hydrophobic environment for the ESIPT reaction, enabling e-PNPs to show strong ESIPT-fluorescence. Upon the addition of Cu(II), the tautomeric fluorescence (t-FL) of e-PNPs is significantly quenched because of the coordination of Cu(II) with e-PNPs. The presence of cysteine (Cys) can elicit the t-FL recovery of e-PNPs–Cu(II) complexes due to the chelation interaction between Cu2+ and the sulfhydryl and amino groups of Cys. Based on this signalling mechanism, the e-PNPs–Cu(II) sensing system was used to detect Cys, and the linear range and limit of detection of the nanosensing system were 0–6.3 μM and 1.8 nM, respectively. As expected, this method was successfully applied to the determination of Cys in rabbit serum and plasma samples with satisfactory recovery ranging from 97.4 to 105.6%. Moreover, e-PNPs–Cu(II) based nanoprobes were employed for imaging Cys in live cells, which demonstrated their potential values for bioanalytical applications.

研究领域: 生物化学 · 分析化学 · 材料科学
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