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AIE
ANALYST · 2022 ·Vol. 147 ·期 18 ·4132-4140 · IF 5.227

Triphenylamine indanedione as an AIE-based molecular sensor with one-step facile synthesis toward viscosity detection of liquids

Lingfeng Xu,Fangzhi Xiong,Minqing Kang,Yanrong Huang,Kui Wu

Viscosity is one of the most important physical parameters in a liquid, noninvasive, and effective viscosity inspection method toward liquid safety that needs to be developed urgently. In this study, two kinds of novel molecular sensors, namely, DPBID and DPTMID, were strategically constructed by the triphenylamine indanedione derivates; the rotatable conjugate structure was utilized as the recognition site and fluorescence quencher. This couple of molecular sensors was synthesized in a one-step facile manner. DPTMID displayed longer emission wavelength and larger Stokes shift (195 nm in water, 138 nm in glycerol) with a narrower energy band. Moreover, DPTMID exhibited high selectivity, sensitivity, and significant fluorescence signal enhancement toward a higher viscous microenvironment. The molecular sensor displayed good photostability, selectivity, and universality in various commercial liquids and featured with typical aggregation-induced emission (AIE). With the aid of DPTMID, the thickening effects of liquid thickeners can be captured. More importantly, DPTMID was explored to visualize the viscosity fluctuations during the metamorphic stages of liquids, and it was found that the microenvironment viscosity level is closely related to the spoilage degree of liquids. The method with rapid detection, high sensitivity, cheap equipment, and fast results output toward food quality and safety inspection can be achieved through this study.

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COLLOIDS AND SURFACES B-BIOINTERFACES · 2016 · IF 3.902

Rapid preparation of branched and degradable AIE-active fluorescent organic nanoparticles via formation of dynamic phenyl borate bond

Zi Long,Meiying Liu,Liucheng Mao,Guangjian Zeng,Qing Wan,Dazhuang Xu,Fengjie Deng,Hongye Huang,Xiaoyong Zhang,Yen Wei

The fluorescent organic nanoparticles (FNPs) with aggregation-induced emission (AIE) feature have received increasing attention for their advanced optical properties. Although many efforts have been devoted to the fabrication and biomedical applications of AIE-active FNPs, the preparation of branched AIE-active FNPs with degradability through formation of dynamic bonds have rarely been reported. In this work, branched AIE-active FNPs were fabricated via dynamic linkage of hydrophobic hyperbranched and degradable Boltorn H40 (H40) with phenylboronic acid terminated AIE dye (PhB(OH) 2 ) and mPEG (mPEG-B(OH) 2 ), which relied on a facile one-pot strategy between phenylboronic acid and diol group of H40. The branched H40-star-mPEG-PhB(OH) 2 FNPs were characterized using nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and fluorescence spectroscopy. Benefiting from their highly branched structure and amphiphilic properties, H40-star-mPEG-PhB(OH) 2 could self-assemble into micelles and emit strong orange-red fluorescence. More importantly, cell viability results demonstrated that H40-star-mPEG-PhB(OH) 2 FNPs showed good biocompatibility and promising candidates for bio-imaging. Taken together, we developed a one-pot strategy for preparation of branched AIE-active FNPs through the formation of dynamic phenyl borate. The resultant H40-star-mPEG-PhB(OH) 2 FNPs should be promising biomaterials for different applications for biodegradability of H40 and responsiveness of phenyl borate.

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MACROMOLECULES · 2023 · IF 5.5

Effects of Plasticizers on Structural Transitions and Heterogeneity of Poly(vinyl alcohol) Films as Studied via AIE Materials

Zhen-zhen Fu,Wei He,Yihang Yao,Ryan Tsz Kin Kwok,Jacky Wing Yip Lam,Ke Wang,Ben Zhong Tang,Qiang Fu

Solution casting is a common processing method in industrial production. The phase-structure transitions driven by solvent evaporation directly impact the quality of the final film. However, due to the presence of solvents and other additives in the solution, it is difficult to detect the condensed matter structure during the drying process. This work studies structural transitions and heterogeneity of a poly(vinyl alcohol) (PVA) film during water evaporation using glycerol as a plasticizer. Aggregation-induced emission (AIE) molecules are utilized to indicate the change in PVA chain dynamics during evaporation. The gelation, crystallization, and glass transition can be clearly detected via emission intensity change of the AIE molecules during water evaporation. It is found that the critical concentrations triggering structural transitions increase with the glycerol content, attributed to the release of PVA segmental mobility by the plasticizer. Furthermore, structural uniformity in the thickness direction is realized while the PVA film was loaded with 20% glycerol. It is revealed that glycerol diminishing the heterogeneity is due to the dual effect of hydrophilic glycerol reducing the evaporation rate and enhancing diffusion. Finally, the mechanism of the plasticizer in delaying structural transitions and ameliorating the heterogeneity in PVA films is discussed, which could provide theoretical guidance for preparation of polymer films via solution casting.

CAS / MDL: 56-81-5
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Surfaces and Interfaces · 2023 · IF 6.2

Monitoring and kinetic study of alkaline hydrolysis of polylactic acid fibrous membrane via aggregation-induced emission (AIE) technique

Chunping Ma,Qiankun Guo,Jinpeng Mo,Fengyuan Lin,Jiayi Chen,Dongdong Cao,Wenyang Xie,Keqi He,Xian Liu,Gaoyi Xie,Yancheng Wu,Yangfan Zhang,Jianrong Chen,Yen Wei

Hydrolysis mechanism of polylactic acid (PLA) materials has been the focus of PLA material research. Herein, we report a novel method for monitoring the hydrolysis of PLA. Tetraphenylene aldehyde (TPEA) with aggregation induced emission (AIE) property was synthesized as a fluorescence probe for being introduced into PLA-base fibrous membrane via electrospinning. Then, the obtained TPEA/PLA composite fibrous membrane was hydrolyzed in an aqueous environment with controllable temperature and pH. The detection of PLA hydrolysis was achieved by examining the fluorescence intensity changes caused by the release of TPEA during the hydrolysis. On the basis of the structure study of the prepared fibrous membranes, this study investigated the changes in fluorescence intensity of the degradation environment during the hydrolysis process. The correlation between fluorescence and PLA hydrolysis was investigated with the kinetic research to prove the feasibility of monitoring PLA hydrolysis via AIE technique.

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CARBOHYDRATE POLYMERS · 2021 · IF 9.381

AIE-active polymeric micelles based on modified chitosan for bioimaging-guided targeted delivery and controlled release of paclitaxel

Haohui Shi,Na Liang,Jiyang Liu,Siyi Li,Xianfeng Gong,Pengfei Yan,Shaoping Sun

In this study, a novel polymer based on aggregation-induced emission (AIE) fluorogen , biotin and disulfide bonds modified chitosan (TPE-bi(SS-CS-Bio)) was designed and synthesized. The polymer could self-assemble into micelles in aqueous media and encapsulate paclitaxel (PTX) into the core with high drug loading. Fluorescence study indicated that the micelles exhibited excellent AIE feature with intense blue fluorescence emitted. In vitro drug release study indicated that the micelles could disassemble rapidly in the presence of high level of glutathione . The modification by biotin could enhance the cellular uptake of the micelles. The drug-loaded micelles possessed remarkable cytotoxicity against MCF-7 cells, and their distribution in the cells could be traced due to the excellent AIE feature. In vivo antitumor efficacy study demonstrated the superior antitumor activity of the PTX-loaded TPE-bi(SS-CS-Bio) micelles. These results indicated that TPE-bi(SS-CS-Bio) has the ability of biological imaging and can be used as a potential carrier for PTX.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2020 · IF 3.232

A novel AIE active NIR fluorophore based triphenylamine for sensing of Hg2+ and CN− and its multiple application

Xiaoye Wen,Li Yan,Zhefeng Fan

New strategies still need to be proposed that can be used to sense and remove toxic environmental pollutants in a sensing system. In this research, a novel NIR fluorescence sensor 1 was designed and prepared with aggregation induced emission (AIE) property. The fluorescence intensity of the sensor 1 in DMSO/H 2 O mixed solvent was changed along with the proportion of water. The sensor 1 can be successfully used for real-time detection and removal of Hg 2+ in 20% DMSO aqueous solution with high selectivity, quick response and so on. Furthermore it can be efficiently reused and recycled without any loss through Na 2 S. In addition, the sensor 1 displayed high sensitivity and selectivity to cyanide ions in 1% DMSO aqueous solution with the presence of other interference anions. The sensing mechanism for Hg 2+ and cyanide ion was evaluated by 1 H NMR spectra, Mass spectrometry. The sensor 1 exhibited low cytotoxicity for biological applications, which was used as an outstanding fluorescent transducer for detection of cyanide ion in living cells. Based on the visible fluorescence change for the sensor 1 to cyanide ion, the measurement was performed for food materials containing cyanide, such as potato, cassava powder and almond. This research provides perspective potential in solving the problem of other pollution and stimulating new thinking for designing of the novel fluorescence materials.

CAS / MDL: 4181-05-9
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APPLIED SURFACE SCIENCE · 2019 · IF 5.155

Two birds one stone: Facile preparation of AIE-active fluorescent polymeric nanoparticles via self-catalyzed photo-mediated polymerization

Jiande Dong,Ruming Jiang,Weimin Wan,Haijun Ma,Hongye Huang,Yulin Feng,Yanfeng Dai,Hui Ouyang,Xiaoyong Zhang,Yen Wei

In this work, we report the first preparation of AIE-active FPNs via metal-free photo-mediated atom transfer radical polymerization (ATRP), employing 2-methacryloyloxyethyl phosphorylcholine (MPC) and benzyl methacrylate (BzMA) as the monomers. Herein, the AIE fluorogen, 10-phenylphenothiazine (PTH)-containing α-bromoester (named as PTH-Br), was simultaneously used as the initiator and photocatalyst. We found that the AIE-active PTH-P(BzMA-MPC)-20(40) FPNs in water can emit intense fluorescence, with high fluorescence quantum yields of 34.3% and 41.2%, respectively, and show excellent water dispersibility and a low critical micelle concentration (CMC). To explore their potential for biomedical applications, biocompatibility evaluation and the cell uptake behavior of these FPNs were further studied. The results demonstrated that these polymeric nanoparticles are biocompatible with L02 cells and are promising for bioimaging applications. Compared with the traditional strategies for preparing AIE-active FPNs, the method described in this work can occur at room temperature, does not require metal catalysts, and is highly efficient. This work lays the foundation for the fabrication of AIE-active functional materials and broadens the potential of AIE-active molecules.

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Analytical Methods · 2019 ·Vol. 11 ·期 27 ·3446-3451 · IF 2.378

Ultrasensitive detection of glutathione based on a switch-on fluorescent probe of AIE-type red-emitting copper nanoclusters

Qianqian Du,Xue Hu,Xiaodan Zhang,Haiyan Cao,Yuming Huang

Glutathione (GSH) plays key roles in biological systems. It is critically valuable to construct highly sensitive and accurate sensors for its quantification in studying the oxidative stress reaction and related diseases. Here, a rapid switch-on fluorescence assay for detecting trace GSH was developed by combining aggregation-induced emission copper nanoclusters (Cu NCs) with a large stokes shift (Δλ = 235 nm) and MnO2 nanosheets. The red-emitting Cu NCs act as a fluorometric reporter, and the MnO2 nanosheets serve as both a fluorescence quencher of Cu NCs and a signal recognizer of GSH. The fluorescence of Cu NCs is quenched by MnO2 nanosheets through the inner filter effect. Upon introduction of GSH, the MnO2 nanosheets were reduced to Mn2+ and the quenched fluorescence of Cu NCs was recovered. On this basis, an ultrasensitive nanosensor was developed for GSH with a detection limit of 1.2 nM, which is at least 5 times lower than that of previous FL sensors based on MnO2. The fluorescence sensing strategy was successfully applied for GSH detection in human serum samples with good accuracy and high reproducibility. The result was cross-verified by standard o-phthalaldehyde fluorescence assay, suggesting the potential applicability of this system for the analysis of GSH in practical biological samples, disease monitoring and clinical diagnosis.

CAS / MDL: 70-18-8 13446-34-9
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Materials Science & Engineering C-Materials for Biological Applications · 2018 · IF 5.08

AIE-active self-assemblies from a catalyst-free thiol-yne click reaction and their utilization for biological imaging

Ruming Jiang,Meng Cao,Meiying Liu,Liangji Liu,Qiang Huang,Hongye Huang,Yuanqing Wen,Qian-yong Cao,Xiaoyong Zhang,Yen Wei

Aggregation-induced emission (AIE) should be the most interest fluorescent phenomenon over the past few decades. The luminescence polymeric nanoparticles (LPNs) with AIE characteristic have attracted great research attention for biological imaging and many other biomedical applications owing to their good biocompatibility and negative toxicity. However, the preparation of LPNs with desirable optical properties using traditional organic dyes still remains a great challenge for the aggregation-caused quenching (ACQ) effect and aggregation of hydrophobic dyes in the core of LPNs. In this work, we reported a novel and simple method for fabrication of biodegradable AIE-active LPNs via the combination of condensation and click reactions. For preparation of these AIE-active LPNs, the thiol groups-containing hydrophilic copolymers (PEG-MA) were first synthesized through the condensation reaction between polyethylene glycol and mercaptosuccinic acid. The PEG-MA copolymers were further reacted with AIE dye PhE-OE through a catalyst-free thiol-yne click reaction. These obtained PEG-MA-PhE LPNs were fully characterized by a number of characterization techniques. All the results confirmed that PEG-MA-PhE LPNs possess excellent compatibility, intense red luminescence, great photostability and high water dispersibility. These features make PEG-MA-PhE LPNs promising candidates for various biomedical applications.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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ANALYST · 2018 ·Vol. 144 ·期 2 ·536-542 · IF 3.864

Two aggregation-induced emission (AIE)-active reaction-type probes: for real-time detecting and imaging of superoxide anions

Hengchang Ma,Manyi Yang,Shaoxiong Zhang,Pei Yin,Tao Wang,Yuan Yang,Ziqiang Lei,Yucheng Ma,Yanfang Qin,Zengming Yang

Fluorescent probes are powerful tools for investigating reactive oxygen species (ROS) in living organisms. The overproduced “primary” ROS of superoxide anions (O2˙−) cause a chain of oxidative damage. In order to monitor O2˙− level fluctuations in living cells, we synthesized two reaction-type probes of TPA-DHP-1,2,3 and TPA-PPA-1,2,3, which were composed of an electron-rich triphenylamine (TPA) and the very active functional groups of dihydropyridine (DHP) and pyridinium (PPA). Intriguingly, DHP and PPA were able to carry out easy proton abstractions and nucleophilic reactions in the presence of O2˙−, resulting in the corresponding products with sharp wavelength shifts, and elevated fluorescence intensities. Therefore, undesirable background fluorescence interference can be reduced during the monitoring and imaging process. Meanwhile, the developed dual-channel monitoring strategy not only provides observations of the O2˙− level fluctuations, but could also be employed to image the dynamic accumulation process of probes in the different cell organelles. Therefore, the design could provide a simple, accurate and universal platform for biological applications in future research work.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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Polymer Chemistry · 2017 ·Vol. 8 ·期 48 ·7486-7498 · IF 5.375

Self-assembled core–shell-corona multifunctional non-viral vector with AIE property for efficient hepatocyte-targeting gene delivery

Bing Wang,Ping Chen,Ji Zhang,Xiao-Chuan Chen,Yan-Hong Liu,Zheng Huang,Qing-Ying Yu,Ju-Hui Zhang,Wei Zhang,Xi Wei,Xiao-Qi Yu

With the aim to develop a novel multifunctional gene delivery system that may overcome the common barriers of gene transfection, two amphiphilic molecules with tetraphenyl ethylene (TPE) as a hydrophobic moiety and linear PEI-galactose as a hydrophilic part were elaborately designed and synthesized. The molecules could self-assemble to form micelles and exhibited aggregation-induced emission (AIE) property, which may be used for cell imaging. Several assays revealed that the disulfide bond in TSPG may facilitate vector decomposition and DNA release, resulting in higher transfection efficiency and lower cytotoxicity than TCPG and PEI 25 kDa. These vectors showed excellent serum tolerance, and even higher efficiency could be obtained in transfection with the presence of serum. Moreover, the transfection in different cell lines showed that TSPG complex could induce higher gene expression in asialoglycoprotein receptor-rich HepG2 cells than in HeLa cells, which lack such receptors. Galactose competition assay also demonstrated that the galactose moiety could afford the vector with targeting ability toward hepatoma cells. Cellular uptake inhibition assay indicated that the DNA complex entered the cell mainly via caveolae-mediated endocytosis. Results showed that TSPG may serve as a promising reagent for simultaneous gene transfection and imaging with good biocompatibility and cell targeting ability.

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Materials Science & Engineering C-Materials for Biological Applications · 2017 · IF 4.164

Preparation of AIE-active fluorescent polymeric nanoparticles through a catalyst-free thiol-yne click reaction for bioimaging applications

Qian-yong Cao,Ruming Jiang,Meiying Liu,Qing Wan,Dazhuang Xu,Jianwen Tian,Hongye Huang,Yuanqing Wen,Xiaoyong Zhang,Yen Wei

Fluorescent polymeric nanoparticles (FPNs) with aggregation-induced emission (AIE) characteristics have attracted much attention for biomedical applications due to their remarkable AIE feature, high water dispersity and desirable biocompatibility. The development of facile and effective strategies for fabrication of these AIE-active FPNs therefore should be of great importance for their biomedical applications. In this work, we reported that a catalyst-free thiol-yne click reaction can be utilized for fabrication of AIE-active FPNs in short reaction time and even without protection of inert gas. The results indicated that the obtained AIE-active amphiphilic copolymers (PEGMA-PhE) can readily self-assemble into luminescent nanoparticles (PEGMA-PhE FPNs) with high water dispersity, uniform size and morphology, red fluorescence. Cell viability examination and cell uptake behavior of PEGMA-PhE FPNs confirmed that these AIE-active FPNs possess low toxicity towards cells and can be easily internalized by cells through non-specific route. Therefore the remarkable properties of PEGMA-PhE FPNs such as high water dispersity, AIE-active fluorescence and nanoscale size as well as excellent biocompatibility make them promising for biomedical applications.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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