Journal of Materials Chemistry C
·
2025
·
IF 5.1
Weiwei Zhang,Yongbo Wei,Fen Lin,Yinyin Yao,Xia Wang,Yongxiao Sun,Jingming Zhou,Tong Wu,Nannan Chen,Yusheng Lu,Xiaoping Wu,Lijun Xie
In this work, a new series of rofecoxib analogues were designed and synthesized by employing the migration of the donor (D) group and donor (D)–acceptor (A) switching principle to achieve ACQ–AIE conversion. Among them, when the D unit dimethylamino was anchored on the para-position of the benzene ring D, the corresponding compound L1, namely (Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one, was obtained exhibiting obvious aggregation-caused quenching (ACQ) behavior. Subsequently, after migrating the D group from ring D to ring B, the resulting L2 exhibits an aggregation-induced emission (AIE) effect. Meanwhile, by switching the position of the D and A units based on the structure of L1, the corresponding compound L3 also shows AIE behavior. These results demonstrate that migrating the position of the donor group and switching the positions of the donor and acceptor have significant effects on the fluorescent properties of the compounds. Moreover, single crystal X-ray analysis of L2 and L3 revealed that the stronger molecular C–H⋯π interactions contribute to greater structural rigidification, which in turn enhances their bright emission in the solid state. In addition, L2 and L3 exhibited solvatochromic, acidichromic, and trace water properties with reversible multi-stimulus behaviors. More importantly, L2 and L3 demonstrated highly specific fluorescent imaging ability (RL2 = 0.97, RL3 = 0.98) toward lipid droplets in living MCF-7 cells, with low cytotoxicity. In summary, the creative design concepts of adjusting the position of D and switching the positions of D and A units, as well as the ACQ to AIE conversion provide alternative ways for developing new multifunctional AIEgens, L2 and L3.
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NEW JOURNAL OF CHEMISTRY
·
2021
·Vol. 45
·期 18
·8155-8165
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IF 3.591
Xiaoye Wen,Li Yan,Zhefeng Fan
As the environmental residues of formaldehyde and hypochlorites are very harmful to human health, a new simple and efficient aggregation-induced emission probe based on diaminomaleonitrile was designed and applied in the independent detection of hypochlorites and formaldehyde. The probe shows high selectivity and anti-interference ability against other potential competitive substances. ClO− promotes the oxidized splitting of CN in the probe, and induces evident color changes visible to the naked eye together with quenched fluorescence. The detection of ClO− by this probe was fast, sensitive, and visible to the naked eye. The detection limit of the probe to ClO− in the range of 0.70–20 μM is 18 nM. Through the condensation mechanism and with amine as the binding site of formaldehyde, the exposed amino group in the probe structure responds sensitively and efficiently to formaldehyde. The probe can effectively monitor 0.50–25 μM formaldehyde in aqueous solutions, with a detection limit as low as 42 nM. A portable solid sensor – a formaldehyde detection plate was built by directly covering the probe on a thin-layer chromatography plate. Thereby, formaldehyde gas can be effectively and sensitively detected, which offers a clue for developing solid-state formaldehyde-detection plates. The high experimental recovery rates prove that this new probe is highly promising in hypochlorite detection in the real water environment.
研究领域:
分析化学
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环境科学
·
生物医学
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ACS Applied Materials & Interfaces
·
2023
·
IF 9.5
Ya-Lan Kou,Jin Tong,Cong Meng,Qing Yuan,Ji Wang,Shu-Yan Yu
Luminescent supramolecular metallacycles have attracted great interest as a new promising class of sensing substrates. In this work, two tetraphenylethene (TPE)-based diimidazole and dipyrazole ligands with the aggregation-induced emission (AIE) feature were designed for the construction of supramolecular tetragonal metallacycles 1–4 with two 90° mononuclear [(bpy)M]2+ or dinuclear [(bpy)2M2]4+ acceptors (bpy = 2,2′-dipyridine; M = Pd, Pt), in which the fluorescence can be quenched to an “off” state due to the ligand-to-metal charge transfer (LMCT). Metallacycle 1 was utilized as a fluorescence sensor for phosphate (PO43–) detection in aqueous solution by means of disassembly, leading to the release of the ligand. Additionally, the metallacycle can be regenerated through self-assembly via the introduction of Pd(II) acceptors. PO43– was detected using TPE-based metallacycles over a wide concentration range, with a detection limit as low as 2.1 × 10–8 M. Furthermore, sensor 1 also presented the semiquantitative visual detection ability for PO43– in the test paper mode via fluorescence changes. The aforementioned studies not only enhance the current research on fluorescent materials but also offer a strategy for the creation of stimuli-responsive supramolecular coordination complexes.
研究领域:
化学
·
生物医学
·
材料科学
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ANALYTICA CHIMICA ACTA
·
2019
·
IF 5.256
Fenghua Geng,Changpeng Zou,Jinhua Liu,Qianchen Zhang,Xueying Guo,Yunchang Fan,Haidong Yu,Sheng Yang,Zhipeng Liu,Lin Li
As an important biomarker, alkaline phosphatase (ALP) is one of the most commonly assayed enzymes in clinical practice. Here a novel turn-on fluorescent nanoswitch for ALP assay was suggested. The nanoswitch was easily constructed via two high-affinity ligands between GSH and Al 3+ and PPi and Al 3+ based on the difference in the affinity. The primary fluorescence of as-prepared GSH capped Cu nanoclusters (NCs) turned on first upon the Al 3+ addition due to the Al 3+ induced aggregation induced emission (AIE) enhancement based on the high affinity of GSH and Al 3+ . The presence of PPi then made Al 3+ desorb from the surface of GSH capped Cu NCs due to the higher affinity of PPi and Al 3+ . As a result, the fluorescence of the Cu NCs was quenched. ALP could hydrolyze PPi into phosphate , destroying the PPi-Al 3+ complex and releasing Al 3+ . Thus, the Al 3+ binds to GSH again and the fluorescence was restored. The nanoswitch was demonstrated to be sensitive and selective for ALP assay and was successfully used for the ALP assay in the human serum.
研究领域:
生物化学
·
医学检测
·
纳米技术
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DYES AND PIGMENTS
·
2021
·
IF 4.889
Zengfang Huang,Chaoyue Zhou,Weirun Chen,Jun Li,Mei Li,Xiaobo Liu,Liucheng Mao,Jinying Yuan,Lei Tao,Yen Wei
In recent years, Aggregation Induced Emission (AIE)-active fluorescent materials have been attracting considerable attention because they play an important role in clinical medicine, photoelectricity , environmental science, biological imaging, and sensors. In this contribution, a novel tetraphenylethylene (TPE) derivative of 2-(4-(1,2,2-triphenylvinyl)benzene) benzothiazole methacrylate (TPBMA) monomer was synthesized by a Suzuki coupling and an acylation reaction using TPE and benzothiazole as structural units, whose maximum emission wavelength respectively appeared at 506 nm in neutral medium and 579 nm in acidic medium with excellent pH sensitivity, and it could change repeatedly at 500 nm and 579 nm under HCl/NH 3 fuming, indicating the reversible fluorescence conversion property. As compared with the TPB dye, the emission wavelength of TPBMA spectra has an obvious red-shift, which is consistent with the transition energy level difference (△E) of highest occupied molecular orbital (HOMO) and lowest unoccupied orbital (LUMO) situation by quantum chemistry calculation. Subsequently, the copolymers PEG-TB were successfully prepared by RAFT polymerization of TPBMA and poly (ethylene glycol) monomethacrylate (PEGMA), and their molecular weight (Mw) was about 2.12 × 10 4 with a narrow polydispersity index (PDI). From the 1 H NMR analysis, the actual fraction of TPBMA in the PEG-TB copolymers increased to 22.6% from 17.4% when the feed ratio of TBMTA changed to 25.0% from 20.0%. The obtained PEG-TB could self-assemble into fluorescent organic nanoparticles (FONs) with 100–150 nm diameter in aqueous solution, and their fluorescence intensity increased gradually with the increase of water fraction in the THF solution, indicating the obvious AIE behavior. Moreover, the as-prepared PEG-TB FONs exhibited the prospective potential in the field of biological imaging due to their low cytotoxicity, excellent biocompatibility and easy cells absorption.
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CHEMICAL ENGINEERING JOURNAL
·
2026
·
IF 12.5
Zuyao Fu,Lingfeng Yang,Yuanyuan Zhang,Xuanjun Zhang,Jing Xie,Zhaoyang Ding
HRP was covalently immobilized on MAF to form a biocomposite with high activity and fluorescence. • HRP@MAF exhibited a remarkable fluorescence quantum yield of 97.77%. • HRP@MAF showed superior substrate affinity with a Km value 25-fold lower than HRP. • A dual-mode colorimetric/ratiometric fluorescent sensor was developed for histamine. Integrating strong fluorescence and efficient biocatalysis within a single metal-organic framework (MOF) is attractive for advanced optical sensing. Herein, a highly emissive metal-organic framework (denoted as MAF) was constructed using ligands with aggregation-induced emission (AIE) properties, followed by horseradish peroxidase (HRP) immobilization to yield HRP@MAF with high catalytic activity and strong fluorescence. The resulting HRP@MAF exhibited a fluorescence quantum yield of 97.77%. Benefiting from the high surface area and porous structure of MAF, HRP@MAF showed markedly improved stability and substrate affinity toward 3,3′,5,5′-tetramethylbenzidine (TMB), with a K m value 25-fold lower than that of free HRP. Based on its catalytic and optical properties, a colorimetric/ratiometric fluorescence sensor was developed for histamine detection with detection limits of 1.71 μM and 0.56 μM, respectively. In addition, smartphone-integrated on-site detection was achieved with linear ranges of 10–1000 μM for the colorimetric mode and 1–1000 μM for the ratiometric fluorescence mode. This work establishes an effective strategy for constructing multifunctional sensing platforms by coupling AIEgens derived highly emissive MOFs with immobilized enzymes. Download: Download high-res image (151KB) Download: Download full-size image
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Journal of Materials Chemistry B
·
2019
·Vol. 7
·期 24
·3846-3855
·
IF 5.047
Bin Wang,Cheng Li,Lijun Yang,Congrou Zhang,Li-Juan Liu,Sen Zhu,Yu Chen,Yong Wang
The development of “turn-on” fluorescence probes for biological thiol detection has received great attention in recent years because abnormal levels of these mercapto biomolecules are always related to some form of disease. In this work, a series of AIE-active polymer probes for biothiol detection were designed and synthesized, comprising disulfide-functionalized hyperbranched poly(amido amine) (ssHPA) as the hydrophilic matrix, tetraphenylethene (TPE) as the hydrophobic AIE-active fluorogen and a disulfide bond as the cleavable functional linkage, defined as TPE-ssHPAs. When these polymers were targeted as “turn on” fluorescence probes for the detection of biothiols, no organic solvents or heavy metal ions were needed as the quencher to eliminate background signals because of the relatively rigid dendritic structure. Upon introducing glutathione or cysteine to an aqueous solution of TPE-ssHPAs, bright fluorescence occurred because of the collapsing of the dendritic structure, leading to the aggregation of TPE units. Further in vitro experiments verified that TPE-ssHPAs is a qualified probe for biothiol detection in living cells. In addition, this strategy of embedding AIEgens inside a relatively rigid hyperbranched polymer offers an effective solution to “pre-quench” the fluorescence of “turn-on” type AIE-active sensors.
研究领域:
分析化学
·
生物化学
·
材料科学
·
生物医学工程
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DYES AND PIGMENTS
·
2022
·
IF 5.122
Chengjian Li,Lijie Ye,Jingwei Sun,Cheng Zhang,Qingbao Song,Kai Wang,Mi Ouyang
A close-bonded D-A-D′ luminophore BOTPA was designed via direct coupling of secondary arylamine derivatives (D, D′) with benzothiadiazole cyanostilbene group (A). Both near-infrared (NIR) aggregation-induced emission (AIE) and hybridized local and charge-transfer (HLCT) effects, which endow it with highly efficient NIR piezochromic performance, are observed owing to its especially short D-A distance and twisted conformation. The luminophore shows bright fluorescence at 740 nm with an absolute photoluminescence quantum yield (PLQY) as large as 13.2%. Remarkable piezochromism with high sensitivity (11.0 nm•Gpa −1 ) completely in the NIR region (700–840 nm) could be observed from BOTPA crystals, which is rarely found in piezochromic materials (PCMs). The effects of the shortened D-A distance towards the highly efficient NIR piezochromism are confirmed via single-crystal analysis, in-situ FTIR and theoretical calculations. This work provides a new strategy for the development of high-efficiency NIR PCMs which possess strong penetrating capacity.
研究领域:
材料科学
·
光学
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TALANTA
·
2019
·
IF 4.916
Lifen Cai,Xiangying Sun,Wei He,Ruolan Hu,Bin Liu,Jiangshan Shen
In this paper, a tetrahydro[5]helicene-based imide dye with thienyl group (THID) was studied on its solvatochromism and aggregation-induced emission (AIE) properties by dissolved in various organic solvents. The linear relationship between Stokes shift and aprotic solvent polarity parameter was well fitted with Lippert-Mataga model. Furthermore, Stokes shift also were positively correlated with the normalized molar electronic transition energy, suggested that THID exceptionally depends on solvent polarity for twisted intramolecular charge transfer. In addition, THID demonstrated typical AIE features when adding large amounts of water into good solvent. Meanwhile, it can function as intensity and wavelength-based fluorescence sensor for detecting low-level water content in water soluble solvents , even the low of detection was 0.014 vol% in ACN . Therefore, a simple and highly selective fluorescence analysis for glyceryl monostearate has been established on basis of its AIE property.
研究领域:
化学
·
材料科学
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Materials Today Bio
·
2022
·
IF 10.761
Shaoqing Chen,Ziyu Wang,Li Liu,Yuting Li,Xinye Ni,Hong Yuan,Cheng Wang
Drug-resistant cancers usually have multiple barriers to compromise the effect of therapies, of which multidrug-resistance (MDR) phenotype as the intracellular barrier and dense tumor matrix as the extracellular barrier, significantly contribute to the poor anticancer performance of current drug delivery systems (DDS). Here in this study, we fabricated a novel aggregation-induced emission (AIE)-active polymer capable of self-assembling into ultrasmall nanoparticles (∼20 nm) with D-alpha Tocopheryl Polyethylene Glycol Succinate (TPGS), for dual-encapsulating of doxorubicin (Dox) and sulforaphane (SFN) (AT/Dox/SFN). It revealed that redox homeostasis modulation of MDR cells (MCF-7/Adr) using AT/Dox/SFN can trigger mitochondria damage and ATP deficiency, which reverse the MDR phenotype of MCF-7/Adr cells to afford enhanced cellular uptake of both drug and DDS in a positive-feedback manner. The enhanced cellular drug accumulation further initiates the “neighboring effect” for improved drug penetration. Using this strategy, the growth of in vivo MCF-7/Adr tumors can be effectively inhibited at a low dosage (1/5) of doxorubicin (Dox) as compared to free Dox. In summary, we offer a new approach to overcome both the intracellular and extracellular barriers of drug-resistant cancers and elucidate the potential action mechanisms, which are beneficial for better cancer management.
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DYES AND PIGMENTS
·
2023
·
IF 4.5
Ensheng Zhang,Long Jiang,He Li,Shuping Wang,Guixue Zhang,Anzhang Li,Weiheng Kong,Yan Zhao,Meihao Xiang,Ping Ju,Fengli Qu
Smart molecules with adjustable and reversible ACQ-AIE transformation which could be used as luminescence sensors both in solvent and solid-state are rarely reported. Planar luminophores with strong inter-molecular hydrogen bonds and a rotor might exhibit reversible ACQ-AIE conversion by modulating the inter-molecular hydrogen bonds. As a proof of concept , herein, two smart hydrogen bond dimers ( Qufu-1 and Qufu-2 ) with reversible ACQ-AIE transformation were derived from the renewable bio-feedstock shikimic acid. Qufu-1 and Qufu-2 possessing a novel 4-oxo-3,4-dihydrobenzofuro[2,3- d ]pyrimidine key structure and both exhibit crystallization induced ACQ (CIACQ) and precipitation induced AIE (PIAIE) in solid-state. Single crystal analysis indicates that the large planar configuration formed in the dimers of Qufu-1 and Qufu-2 due to the inter-molecular hydrogen bonds, which would result in the strong π-π stacking and ACQ in crystal. The AIE state could be facile realized by breaking the inter-molecular hydrogen bonds and changing the aggregation state from crystal to precipitation. Moreover, ACQ to AIE transformation could also accomplish for Qufu-1 and Qufu-2 in solution by modulating the inter-molecular hydrogen bonds with acid. In addition, three-level structures latent fingerprint identification in real environment and fluorescent sensing of hazardous biogenic amines in food samples were performed with Qufu-1 .
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
·
2023
·
IF 4.4
Na-Na Li,Xing-Yu Xu,Ping Qiu,Yong-X Li,Xiong-Sheng Yu,Yong-E Gao,Hai-Xian Ren,Mohd. Muddassir,Wan-Ying Lin,Zi-Ao Zong
Erythromycin could be used to treat various bacterial infection, but it was harmful to the colonic microflora. Therefore, it is highly desirable to develop a fluorescence probe that could selectively and sensitively detect Erythromycin in pure water. In this work, a fluorescent probe named EHMC , which exhibited aggregation-induced emission (AIE) characteristic in solid state and water/EtOH binary solvent was developed for “turn on” sensing Erythromycin in pure water with high selectivity and sensitivity (detection limit: 1.78 × 10 −8 M). Also, there are fewer interference from other antibiotics in the detection process of probe EHMC for Erythromycin. Moreover, probe EHMC could as a portable test strips for highly selective detection of Erythromycin and identification of different concentrations of Erythromycin. In addition, living cells imaging experiments displayed that probe EHMC could detect Erythromycin in A549 cells and BEAS-2B cells successfully. Combined with the theoretical calculation results The sensing mechanisms that the C O in Erythromycin and OH in EHMC formed intermolecular hydrogen bond and further formed new aggregates were confirmed by job’ plot, 1 H NMR, FT-IR, ESI-MS, DLS and TEM and DFT calculation.
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