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AIE
RSC Advances · 2020 ·Vol. 10 ·期 68 ·41424-41429 · IF 3.119

Thermally responsive AIE-active polyurethanes based on a tetraaniline derivative

Beibei Liu,Kun Wang,Hao Lu,Mingming Huang,Zhigang Shen,Jiping Yang

Polyurethanes with different soft–hard segment ratios were successfully synthesized, with an aggregation-induced-emission (AIE)-active tetraaniline derivative (NH2–B3–Ani4–NH2) as the hard segment. The resulting polyurethanes exhibited typical AIE features. The fluorescence intensities of polyurethane films changed with heat treatments. The fluorescence intensities of the polyurethane films decreased sharply after quenching treatment, yet their fluorescence intensities exceeded the original intensities of the films after thermal annealing at 80 °C for 24 h. Differential Scanning Calorimetry (DSC) results implied that the melting peaks in polyurethane films disappeared after quenching treatment, but the melting peaks appeared again after thermal annealing. These results proved that the arrangement of the structure had an important effect on the AIE properties of the polyurethane films. Meanwhile, the fluorescence intensities of these polyurethanes decreased with the increase of temperature, indicating that all three polyurethanes exhibited temperature-dependent fluorescent characteristics. Based on the above investigations, the AIE-active polyurethanes may provide a platform for the development of stimuli-responsive fluorescent materials.

CAS / MDL: 101-68-8 25190-06-1
研究领域: 材料科学 · 化学
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CHEMICAL ENGINEERING JOURNAL · 2021 · IF 13.273

A triple pH-responsive AIEgen: Synthesis, optical properties and applications

Weihua Luo,Bo Wu,Xingtang Xu,Xiaolin Han,Jichao Hu,Guojie Wang

Stimuli-responsive luminogens with aggregation-induced emission (AIE) properties have attracted more and more attention for their intense emission in the aggregated state and tunable physicochemical performances. Nevertheless, it still remains challenging to design multifunctional AIE luminogens (AIEgens) with multi-responsive moieties and tunable fluorescence and morphologies. Here, a novel multifunctional AIEgen (DAS-BA) is elaborately designed based on the synergistic effect of twisted intramolecular charge-transfer (TICT), restriction of intramolecular motions (RIM), and excited-state intramolecular proton transfer (ESIPT). DAS-BA not only possesses triple pH-responsivenesses and long-wavelength emission, but also shows corresponding transition in its fluorescence and self-assembled morphologies. Under strong alkaline conditions, owing to the deprotonation of phenolic hydroxyl group, the red emission of DAS-BA is quenched and the molecular assemblies change from micro-rods to nano-rods. However, under weak acidic conditions, the red fluorescence dramatically shifts to yellow-green and the assemblies strikingly transform from micro-rods to nano-spheres due to the protonation of diethylamino moieties. Further acidification can hydrolyze the Schiff base, resulting in fluorescence quenching and destruction of the nano-spheres. Based on the reversible protonation process of diethylamino moiety, DAS-BA exhibits CO 2 -activated reversible fluorescence switching. Furthermore, DAS-BA has been successfully applied in anti-counterfeit and dual encryption, photo-patterning and molecular logic gates.

CAS / MDL: 767-64-6
研究领域: 材料科学 · 光学 · 化学
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Preparation and application of wormlike micelles generated from a rosin-based aggregation-induced emission surfactant through coordinating aggregation

Wenjing Zhang,Shengfeng Ye,Zhaolan Zhai,Dan Wang,Shibin Shang,Zhanqian Song

Fluorescent nanomaterials have drawn considerable attentions due to their high fluorescence sensitivity, excellent signal stability and tunable luminescent properties. A bio-based aggregation-induced emission (AIE) surfactant (Sodium 4-(tetraphenylstyrene)maleate, MPA-TPE-Na) was prepared from rosin, which showed typical AIE characteristic, obvious solvatochromism and a large Stokes shift (>100 nm). AIE viscoelastic solutions were further prepared by complexing MPA-TPE-Na and cetyltrimethylammonium bromide (CTAB) through coordinating aggregation and their microstructure, fluorescence properties and viscoelasticities were investigated. The aggregates in the viscoelastic solutions were wormlike micelles. As the concentration of MPA-TPE-Na increased, the fluorescence intensity of the viscoelastic solutions increased, and their viscosity increased at first and then decreased. The fluorescence emission intensity of the viscoelastic solutions was barely affected by the change in pH. But reducing the pH could increase its viscosity. This system can specifically recognize Fe 3+ without any organic solvent and has anti-interference ability. The present work provided a bio-based fluorescent nanomaterial and verified the feasibility of preparing aqueous AIE nanomaterials by modifying AIE groups with rosin skeleton.

研究领域: 材料科学 · 化学 · 生物技术
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2021 · IF 4.291

Crown-ether-bridging bis-diphenylacrylonitrile macrocycle: The effective fluorescence sensor for oxytetracycline

Yunmei Wu,Sining Zheng,Yanying Ye,Hongyu Guo,Fafu Yang

This work reported the novel organic fluorescence sensor for oxytetracyline based on a novel AIE-macrocycle. By “1 + 1” condensation of diphenylacrylonitrile bearing OH groups and its derivative with terminal Cl groups, the crown-ether-bridging bis-diphenylacrylonitrile macrocycle ( CBP ) was prepared in quantitative yield of 38 %. CBP exhibited strong AIE fluorescence at 430−550 nm in aqueous media. It presented good selective sensing ability for oxytetracyline with dramatically fluorescence quenching among all kinds of ions and biomolecules. The detection limit was as low as 1.33 × 10 −7 M. The sensing mechanism was confirmed as 1:1 stoichiometric ratio. This detection ability was successfully applied on sensing oxytetracycline in test strip and biological samples. Moreover, CBP displayed good sensing ability for oxytetracycline in living cells based on its good living-cell fluorescence imaging property. This paper not only provided the novel organic fluorescence sensor for oxytetracyline, but also opened a new strategy based on AIE-macrocycle to construct the novel sensor for complex biomolecules.

研究领域: 化学 · 生物学 · 医学
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DYES AND PIGMENTS · 2024 · IF 4.1

Protonation regulates intermolecular interaction force to achieve reversible ACQ-AIE conversion

Junliang Zhou,Zhiwei Ma,Haiyang Wang,Wen Wang,Kaijin Chen,Hongxing Gui,Zhenguo Chi,Siwei Liu

In recent years, there has been a lot of focus on aggregation-induced emission materials, and most of the research has focused on the unidirectional conversion from ACQ (aggregation-causing quenching) to AIE (aggregation-induced emission), which inevitably requires complex chemical synthesis and cumbersome processes, and molecules with reversible ACQ and AIE conversion characteristics are rarely reported. In order to achieve a reversible conversion based on a single material between ACQ and AIE properties, we have developed a new functional material , DBPZ-2 (1,4-bis((4-(benzo[c] (Li et al., 2020; Hu et al., 2014; Song et al., 2024) [1,2,5]thiadiazol-4-yl)piperazin-1-yl)methyl)benzene). This compound exhibits AIE properties under neutral conditions, and interestingly, it exhibits significant ACQ properties when protonated, and then restores AIE properties after simple deprotonation . Furthermore, the sensitive response of DBPZ-2 to pH can be used as a fluorescent probe to monitor the changes in the pH value of cellular lysosomes , which brings hopes for future research on lysosomal biology and related diseases.

研究领域: 化学 · 材料科学 · 生物学 · 医学
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Soft Matter · 2020 ·Vol. 16 ·期 45 ·10368-10376 · IF 3.14

Room-temperature AIE ionic liquid crystals based on diphenylacrylonitrile-imidazole salts

Hongyu Guo,Qi Yu,Yuzhi Xiong,Fafu Yang

Although various AIE liquid crystals have been studied, AIE ionic liquid crystals (ILCs) are almost unknown to date. In this work, a series of novel AIE ILCs based on diphenylacrylonitrile-imidazole salts bridged by soft spacers with different anions were prepared in yields of 63–80%. The mesomorphic, photophysical and electrochemical properties were investigated systematically to elucidate the relationship between structures and properties. The results implied that they were the first room-temperature AIE ILCs with wide ranges of mesomorphic temperature, good fluorescence emission in both the solid state and mesophase, and stable electrochemical behaviour. The samples with one alkyl chain possessed the SmA2 mesophase while the samples with two alkyl chains prefered the Colh mesophase. The larger anions resulted in the bigger layer spacing length for the SmA2 mesophase and smaller values of ncell in each slice of Colh mesophase. The fluorescence quantum yields in the mesophase maintained reasonable values (0.15–0.22), which decreased a little in comparison with that in solid films (0.18–0.26) due to the orderly molecular stacking in the mesophase. The cyclic voltammetry experiments confirmed that all of them possessed similar and stable electrochemical behaviour. This research not only presented the first room-temperature AIE ILCs with excellent mesomorphic, photophysical and electrochemical properties, but also elucidated the relationship between structures and properties to a certain degree, contributing to the further construction of novel AIE ILCs with excellent mesomorphic, photophysical and electrochemical properties.

研究领域: 材料科学 · 化学
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ACS Applied Materials & Interfaces · 2018 · IF 8.097

AIE-Active Polyamide Containing Diphenylamine-TPE Moiety with Superior Electrofluorochromic Performance

Ningwei Sun,Kaixin Su,Ziwei Zhou,Ye Yu,Xuzhou Tian,Daming Wang,Xiaogang Zhao,Hongwei Zhou,Chunhai Chen

Electrofluorochromism has attracted great attention due to the intelligence optoelectronic and sensing applications. The intrinsically switchable fluorophores with high solid-state fluorescence are regarded as key for ideal electrofluorochromic materials. Here, we reported an AIE-active polyamide with diphenylamine and tetraphenylethylene units, showing high fluorescence quantum yield up to 69.1% for the solid polymer film and stable electrochemical cycling stability. The polyamide exhibited reversible color and emission switching even in hundreds of cycles, and the fluorescence on/off contrast ratio was determined up to 417, which is the highest value to our knowledge. Furthermore, as the response time is vital for the real-life applications, to speed up the response of electrofluorochromism, a porous polymer film was readily prepared through a facile method, notably exhibiting high fluorescence contrast, long-term stability and obviously improved response, due to the sharply increased surface area. Therefore, the AIE-functionalization combining the porous structure strategy will synergistically and dramatically improve the electrofluorochromic performance, which will also promote their practical applications in the near future.

研究领域: 材料科学 · 光学
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CHEMICAL ENGINEERING SCIENCE · 2024 · IF 4.1

Robust, self-healing AIE fluorescent supramolecular elastomers for smart anti-counterfeiting

Jun Huang,Weijing Yao,Xijin Cui,Libo Si,Dai Yang,Xuying Liu,Wentao Liu

Providing aggregation-induced emission (AIE) polyurethane with self-healing capability can increase the lifetime of the material and adapt it to multiple application scenarios, which is a huge challenge in the development of luminescent smart materials. Herein, a range of transparent fluorescence polyurethanes (FPUs) with prominent strength were designed and synthesized. The optimization of robust FPUs exhibits outstanding mechanical performance (33.5 MPa tensile strength, 120.2 MJ m −3 toughness) and self-healing ability (88.9 %, at 80 °C for 2 h). Furthermore, the aggregation of tetraphenylethylene structure in the hard segment causes the system to emit bright blue fluoresence. We successfully screen-printed designable patterns on the self-healing polyurethane substrates. The concealed patterns self-repair after damage, and can be clearly and robustly displayed under 365 nm light irradiation. The as-prepared multifunctional self-healing material, exhibiting stable AIE fluorescence, is anticipated to possess significant value in the domains of smart anti-counterfeiting materials, flexible display screens and intelligent optoelectronics.

CAS / MDL: 1892-29-1
研究领域: 材料科学 · 光学 · 智能材料
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LUMINESCENCE · 2026 ·Vol. 41 ·期 4 ·e70468 · IF 2.8

AIE Fluorescent Probes Constructed by Introducing Acceptor-Derived Microbial Metabolite Staurosporine

Jingming Zhou,Xia Wang,Shijie Liu,Yuqiu Ye,Xuejing Su,Tong Wu,Yusheng Lu,Xiaoping Wu,Lijun Xie

The aggregation-caused quenching (ACQ) phenomenon limits the bioimaging application of traditional fluorescent probes. To address this, we developed a novel strategy to convert ACQ-type bioactive Staurosporine analogues into aggregation-induced emission (AIE) luminogens by constructing a donor–acceptor system via the introduction of cyano units as strong electron-withdrawing groups. First, we successfully developed a novel fluorescent scaffold based on the skeleton of Staurosporine, which is a kind of microbial secondary metabolite. Next, we synthesized three derivatives ( STY1 – 3 ) by introducing a new rotor via one-step structural modification. These three compounds exhibited tunable AIE fluorescence and retained significant bioactivity. Cellular imaging demonstrated their capacity to outline cell contours with low background interference, while cytotoxicity assays revealed potent antitumor activity against NCI-N87 and MCF-7 cell lines. This work provides a design method for developing bioactive AIE probes from natural ACQ scaffolds.

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DYES AND PIGMENTS · 2016 · IF 4.055

Reversible multicolor switching via simple reactions of the AIE-characteristic molecules

Yahui Zhang,Lingwei Kong,Xiaoling Pan,Huiling Mao,Xiangkai Zeng,Jianbing Shi,Bin Tong,Yuping Dong

A multicolor switching was achieved via simple reversible coordinationand acetalation reaction between aldehydes, tri(pentafluorophenyl)borane (BCF) and methanol. The coordination [HPB → BCF] of 4,4′-[(1E,3E)-1,2,3,4-tetraphenylbuta-1,3-diene-1,4-diyl]- dibenzaldehyde ( E,E- HPB) to tri(pentafluorophenyl)borane can change the emissive wavelength from 550 to 630 nm, while transformation of the aldehyde into acetal can change the emissive wavelength from 550 to 530 nm in the presence of methanol. More important, these reactions can access reversibility easily and tune the emission color repeatedly between cyan, yellow and red. All of these dyes show typical aggregation-induced emission (AIE) or aggregation-enhanced emission (AEE) characteristics. In addition, a tunable photoluminescence mechanism is proposed based on the characterization data including NMR , XRD , MS and IR. The result may provide a new design strategy for the multicolor switches and their related applications.

研究领域: 化学 · 材料科学
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GREEN CHEMISTRY · 2026 · IF 9.2

The AIE-Active Flavonoids in Orange Peel for Photocatalytic Oxidation Reactions

Zhuxin Li,Junfei Zhang,Chong Li,Jinzhe Cao,Shengyang Tao

Photochemical organic synthesis has emerged as a prominent and important synthetic methodology in recent years. However, conventional photosensitizers are often expensive and require multi-step synthesis for their preparation. This study utilizes natural flavonoids extracted from citrus peel (Tangeretin, Nobiletin, and Sinensetin) as photocatalysts to achieve the photooxidation of alkenes. Conversion rates of 53.7% for styrene and 66.1% for cyclohexene were attained. Reaction Mechanism Generator (RMG) simulations revealed that alkenes undergo reaction pathways mediated by singlet oxygen or oxygen-free radicals to form the corresponding products, a finding corroborated by a series of control experiments and EPR. These flavonoid compounds exhibit Aggregation-Induced Emission (AIE) characteristics. Upon encapsulation with saponins to form nanoparticles, the conversion rate for cyclohexene was further enhanced to 86.0%. Furthermore, this system successfully achieved the efficient oxidation of benzyl alcohol in an aqueous solvent (52.4% conversion, >99% selectivity). This work establishes a comprehensive green chemistry system encompassing the light source, catalyst, and solvent. The proposed strategy offers a novel approach to the development of natural photocatalysts and sustainable organic synthesis.

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MACROMOLECULAR RAPID COMMUNICATIONS · 2021 ·Vol. 42 ·期 14 ·2100174 · IF 5.734

Significantly Red-Shifted Emissions of Nonconventional AIE Polymers Containing Zwitterionic Components

Qing Huang,Jiaqi Cheng,Yuran Tang,Yongqiong Wu,Dan Xia,Yuchen Zheng,Mingming Guo

Nonconventional luminescence polymers without any aromatic structures have attracted great interest from researchers due to their special structure and excellent biocompatibility. However, these materials mostly emit in the blue or green region, in which preparation of materials with long-wavelength (especially near-infrared) emission is still a great challenge. In this work, it is found that 2-(dimethyl amino) ethyl methacrylate (DMA) and itaconic anhydride (ITA) undergo a ring-opening reaction at room temperature, and subsequently generate zwitterionic compound (IDMA). Based on the clustering-triggered emission (CTE) mechanism, ionic bond can effectively promote the isolated electron-rich chromophores to form new emissive clusters with extended electron delocalization. Herein, two oligomers (P1 and P2) with different fluorescence emissions by controlling the concentration of zwitterionic monomers before polymerization are synthesized. It is worth noting that the maximum emission wavelength of P2 at high concentration is up to 712 nm, which is very rare in previous reports. In addition, the resulting oligomer (P2) shows typical aggregation-enhanced emission (AEE), excitation-dependent fluorescence, temperature-sensitive emission, and solvatochromism. The cytotoxicity assay demonstrates that P2 was low toxic to Huh7 and LM3 cells, and suitable for cell imaging. This research provides the possibility for rational molecular design and the feasibility of luminescence regulation.

研究领域: 材料科学 · 生物医学工程 · 高分子化学
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