NEW JOURNAL OF CHEMISTRY
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2023
·Vol. 47
·期 14
·6916-6923
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IF 3.3
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
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环境科学
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生物医学
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DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2019
·
IF 4.561
Chaofan Sun,You Li,Bo Li,Jianhui Han,Qiao Zhou,Hang Yin,Ying Shi
The relationships between the excited state intramolecular proton transfer (ESIPT) behaviors and antioxidant activities of three hydroxyanthraquinone (HAQ) compounds containing 2,6-DHAQ, 1,5-DHAQ and 1,5-DAAQ were systematically explored via the experimental and theoretical methods. The measured femtosecond transient absorption indicates that 1,5-DAAQ exhibits the slower ESIPT reaction than 1,5-DHAQ due to its larger S 1 -state energy barrier in the scanned potential energy surfaces , which means that the transformation of 1,5-DAAQ from enol form to keto form is more difficult. Based on this, the antioxidant activities of the compounds in enol- and keto-form were studied. Concretely, the antioxidant activities of 1,5-DHAQ and 1,5-DAAQ in the keto form are stronger than that in the enol form, which is estimated from the calculated ionization potential (IP) values. In addition, compared with that at the S 0 state, the involved three compounds in the enol and keto forms have the lower IPs at the S 1 state, revealing that their antioxidant activities will be enhanced upon the photo-excitation. Derived from the difficulty of ESIPT reactions and antioxidant activities of the three compounds in the experiments and theory, it can be concluded that antioxidant activity of the compound can be regulated through the transformation of enol- and keto-form in the ESIPT reaction. This new discovery can help to design and synthesize more efficient ESIPT-based antioxidants in experiments.
研究领域:
化学
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生物学
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高影响因子
RSC Advances
·
2016
·Vol. 6
·期 68
·63874-63879
·
IF 3.289
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
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材料科学
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分析化学
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DOI
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2024
·
IF 4.3
Xingzhu Tang,Lingling Wang,Yajie Zhang,Chaofan Sun
Antioxidant activity, as a topic of current interest, is discussed together with the excited state intramolecular proton transfer (ESIPT) process for three flavonoid derivatives, based on density functional theory (DFT)and time-dependent DFT (TD-DFT) methods, as well as DPPH free radical scavenging assay. The potential energy curves and transition states demonstrate that the three molecules can undergo only single proton transfer in the excited state, and all of them are ultrafast ESIPT processes. The absorption spectra of all the molecules show effective protection against UV radiation with low fluorescence intensity, especially Baicalein (Bai), which demonstrates their great potential for sunscreen applications. The density of states, HOMO energy values, global and local indices reveal that the antioxidant activity of the molecules after ESIPT process is enhanced, with Bai having the highest antioxidant activity, which is significantly attributed to the number and position of phenolic hydroxyl groups. Moreover, by comparing the DPPH free radical scavenging activity under the dark and UV radiation conditions, the radical scavenging activity (RSA) value in the UV radiation is remarkably higher than that in the dark condition, in which Bai achieves RSA value of 93.4%. Overall, the antioxidant activity of all three ESIPT-based flavonoid derivatives, especially Bai, is significantly elevated in the keto* form, which reinforces the significant relationship between antioxidant activity and ESIPT process, and provides new application prospects for molecules with ESIPT properties.
研究领域:
化学
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生物学
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DOI
PubMed
高影响因子
ACS Applied Materials & Interfaces
·
2024
·
IF 8.3
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
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分析化学
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生物化学
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DOI
PubMed
高影响因子
DYES AND PIGMENTS
·
2019
·
IF 4.018
Xiaojun He,Wei Xiong,LileiZhang,Chuchu Xu,Jinyi Fan,Yuna Qian,Jinsheng Wen,Feng Ding,Jianliang Shen
Gallium , aluminum , and indium belong to Group IIIA of the periodic table with similar chemical properties, which were a double-edged sword for living organisms. Therefore, it's particularly important to detect the content of Group IIIA in organisms. Obviously, the fluorescent probe method has become a mainstream method for detecting metal ions with advantages of convenience and high efficiency. Unfortunately, fluorescent probes that can simultaneously detect these three metal ions are rarely reported. 3-hydroxyflavone ( 3-HF ) is a highly focused molecule with chemical and photochemical properties and have great potential for bioimaging applications as sensors with excited-state intramolecular proton transfer (ESIPT). Here, 3-HF as ratiometric fluorescence probes have been developed for responding to Group IIIA ions including Ga(III), Al(III) and In(III) ions with ESIPT-based mechanism. 3-HF displayed highly specific sensing for Group IIIA ions over other cations with a green fluorescence transformation into blue fluorescence by the formation of 2:1 complexes. However, rapid response toward Group IIIA ions was developed using ratiometric fluorescence with wide pH range and good reversibility , and the response mechanism of 3-HF toward Group IIIA ions was annotated by density functional theory (DFT). Furthermore, the biological applicability of 3-HF has shown that 3-HF were able to detect and image Group IIIA ions in cells. Additionally, using a zebrafish model, we exhibited the capability of this 3-HF probe for detecting and imaging Group IIIA ions in zebrafish. This work achieves the detection and imaging of Group IIIA simultaneously by 3-HF probe in living cells and zebrafish and provides another example for “ESIPT OFF”.
研究领域:
分析化学
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生物医学
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材料科学
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DOI
高影响因子
BIOORGANIC CHEMISTRY
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2021
·
IF 5.275
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.
研究领域:
分析化学
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生物医学工程
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环境科学
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DOI
PubMed
高影响因子
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
·
2024
·
IF 4.1
Yuxiang Jiao,Yifei Li,Huaijun Tang,Shanglan Xian,Yonghui He,Long Wang,Jinghao Zhang
Herein, a cationic iridium(III) complex [(ppy) 2 Ir(IPP)]PF 6 (ppy: 2-phenylpyridine; IPP: 2-(1 H -imidazo[4,5- f ][1,10]phenanthrolin-2-yl)phenol) was synthesized. Under the excitation of 328 nm (λ ex = 328 nm) UV light, this complex emitted bright yellow orange light (500 ∼ 700 nm, λ em,max = 582 nm), the Stokes shift was up to 254 nm, mainly due to excited-state intramolecular proton transfer (ESIPT) occurring in its ancillary ligand IPP. [(ppy) 2 Ir(IPP)]PF 6 was very sensitive to Ni 2+ , which was caused by the ESIPT being hindered by the coordination of [(ppy) 2 Ir(IPP)]PF 6 with Ni 2+ . Its bright yellow orange light disappeared within 1 min when Ni 2+ (1.0 equiv.) was added in its solution (in DMSO/H 2 O, v/v = 999/1), therefore, it can be used for “turn-off” chemiluminescent detection of Ni 2+ . The recognition of [(ppy) 2 Ir(IPP)]PF 6 to Ni 2+ was not interfered by many common metal ions (such as Na + , K + , Li + , Mg 2+ , Al 3+ , Ca 2+ , Fe 3+ , Ag + , Zn 2+ , Hg 2+ , Co 2+ , Pb 2+ , Mn 2+ , Ba 2+ or Cr 3+ ), however, Cu 2+ was an interfering metal ion, but its interference can be completely masked by thiourea. The detection limit was as low as 3.31 × 10 −7 mol∙L -1 (0.331 μM). The Job’s plot analysis revealed that the stoichiometry of [(ppy) 2 Ir(IPP)]PF 6 with Ni 2+ was 1:1, its detecting mechanism based on ESIPT effect was demonstrated by 1 H NMR spectra and density functional theory (DFT) calculation.
研究领域:
化学
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分析化学
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材料科学
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DOI
高影响因子
RSC Advances
·
2022
·Vol. 12
·期 48
·31186-31191
·
IF 4.036
Dandan Jiang,Minghao Zheng,Xiaoyang Yan,Bin Huang,Hui Huang,Tianhao Gong,Kunming Liu,Jinbiao Liu
Herein, we report a highly selective fluorescent probe for the detection of Cu(II). The detection mechanism relies on the Cu(II)-catalyzed oxidative hydroxylation of 2-(aminocarbonyl)phenylboronic acid into salicylamide, thus recovering the excited-state intramolecular proton transfer (ESIPT) effect and inducing more than 35-fold fluorescence enhancement. The simple structure and readily available fluorescent probe give a novel method for quantitatively detecting Cu(II) in the linear range of 0–22 μM, with a limit of detection down to 68 nM, and exhibiting high selectivity for Cu(II) over 16 other metal ions.
研究领域:
分析化学
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材料科学
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光谱学
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DOI
PubMed
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2019
·Vol. 43
·期 20
·7620-7627
·
IF 3.069
Peng Zhang,Yuzhe Xiao,Qian Zhang,Zixuan Zhang,Hongwei Yu,Caifeng Ding
Cysteine (Cys) is an important amino acid containing a sulfhydryl group, and it is involved in cellular growth and an abnormal level of Cys in vivo is suggestive of many diseases. Hence, development of fluorescent probes for intracellular Cys detection and imaging is of pivotal importance. So far, a number of fluorescent probes have been developed for Cys detection successfully. However, many of them could hardly discriminate Cys from Hcy, GSH or other reactive sulfur species (RSSs) and the emission wavelength of the probes is mainly located in the ultraviolet/short wavelength region with small Stokes shifts (<100 nm). Herein, based on the impressive fluorescence properties of the ESIPT process, a new fluorescent probe named ABT-MVK is synthesized and used to detect Cys. This probe utilizes a typical ESIPT dye (HBT) as the fluorophore and an acrylate group as the ESIPT blocking agent as well as a recognition unit. Cleavage of the acrylate moiety can be achieved by Cys rapidly and specifically in aqueous buffer, which restores the ESIPT process and endows the probe with a “Turn ON” fluorescence detection feature with a large Stokes shift (ca. 225 nm) for Cys with superior selectivity over various potential interferents, including Hcy, GSH, Na2S or NaHSO3. The detection limit for Cys was calculated to be as low as 19 nM and intracellular bio-imaging of Cys by this probe was successfully applied in living cells, indicative of great potential for biological applications.
研究领域:
分析化学
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生物化学
·
生物成像
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DOI
高影响因子
RSC Advances
·
2023
·Vol. 13
·期 34
·23812-23817
·
IF 3.9
Gao Liang,Zheng Minghao,Liu Haiyi,Xiao Jun,Gong Tianhao,Liu Kunming,Li Juanhua,Liu Jinbiao
A 2-(2′-hydroxyphenyl)benzimidazole (HBI)-based ratiometric fluorescent probe, known as BTEP, was synthesized using 5-bromosalicylaldehyde as the raw material via Sonogashira coupling and condensation reaction. This probe was designed for rapid detection of boron trifluoride solutions and gases. The N and O coordination atoms in the probe undergo a boron difluoride addition with BF3, which affects the process of excited state intramolecular proton transfer (ESIPT) leading to a blue shift of fluorescence emission. Obvious changes in the fluorescence signal can be observed within 60 seconds. The introduction of an acetylene trimethylsilane fragment increases the conjugate plane and is beneficial to improving the selectivity of the probe. The I408/I479 fluorescence ratio of the probe displays a linear relationship with the concentration of BF3 in the range of 5–50 μM, with a detection of limit as low as 69.5 nM. Furthermore, the probe demonstrates specific and selective recognition of BF3 among eight common interference substances. Test strips prepared using BTEP have the capability of real-time naked-eye detection of trace BF3 gas.
研究领域:
分析化学
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材料科学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF LUMINESCENCE
·
2012
·
IF 2.102
Shujuan Xu,Yong Shao,Fei Wu,Guiying Liu,Lingling Liu,Jian Peng,Yanwei Sun
Many efforts have been made for sequence-specific recognition of DNA by small molecules. In this study, abasic site (AP site) in a DNA duplex was found to be targeted by myricetin (Myr), one of the natural 3-hydroxyflavonols. Steady-state and transient-state fluorescence, FRET , and DNA melting experiments confirmed that the AP site binding of Myr favors an emission from its tautomer that is derived from excited-state intramolecular proton transfer (ESIPT) reaction between the 3-OH and 4-carbonyl moieties. The selective recognition of Myr is less dependent on the flanking bases of the AP site, although the ESIPT emission is more lighting up for the DNAs with cytosine and thymine opposite the AP site. Because Myr alone in aqueous solution is non-fluorescent, this selective lighting-up emission is advantageous for developing a practical sensor to target the DNA AP site with a weak fluorescence background. This selective recognition of the AP site by the lighting-up fluorescence response would find wide applications including efficiently evaluating DNA damage/repair and screening antitumor/antioxidation drugs.
研究领域:
化学
·
分子生物学
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生物化学
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）