JOURNAL OF MOLECULAR STRUCTURE
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2025
·
IF 4.7
Lina Guo,Ligang Yan,Ruijun Xie,Limin Han,Ning Zhu
In this work, we investigate a palladium complex exhibiting aggregation-induced emission enhancement (AIEE) properties and remarkable solvatochromism behavior driven by structural changes arising from solvent-solute interactions. Specifically, in polar aprotic solvents, the color of the Pd complex changes from blue to purple as solvent polarity increases, accompanied by a blue shift in the UV–Vis spectrum. Notably, this blue shift is even more pronounced in polar protic solvents, which also show a significant increase in fluorescence emission. These effects are likely driven by hydrogen-bond interaction between the protic solvents and the Pd complex. Density Functional Theory (DFT) calculations show that increased solvent polarity significantly alters the electronic distribution of the Pd complex. Higher solvent polarity leads to a higher orbital transition energy, resulting in a blue shift in the UV–Vis absorption spectrum. X-ray single-crystal structure analysis further reveals that hydrogen-bonding interactions between the Pd complex and methanol stabilize its planar structure. When water is introduced, the Pd complex undergoes aggregation through non-covalent interactions, which modify the stacking arrangement. This change weakens the π-π interactions between adjacent molecules, thereby minimizing energy loss in the system. Consequently, the Pd complex effectively utilizes the AIEE mechanism to detect water content in methanol.
研究领域:
化学
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材料科学
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DOI
高影响因子
RSC Advances
·
2017
·Vol. 7
·期 48
·30229-30241
·
IF 3.108
Kai Li,Yang Zhang,Bing Qiao,Furong Tao,Tianduo Li,Yunqiao Ding,Françisco M. Raymo,Yuezhi Cui
Four barbituric derivatives (1–4), were synthesized with obvious aggregation induced emission (AIE) or aggregation induced emission enhancement (AIEE) behaviors. The optical properties in different states and the mechanisms of the enhanced emission of 1–4 were investigated. We found that there were a large number of globular or blocky nanoparticles with average diameters from 229 to 394 nm in tetrahydrofuran (THF)/water solutions when the water fraction (fw) was 90%. The single crystal data of 2 and 4 reveal that multiple intermolecular interactions restrict the intramolecular motions, and promote the formation of a herringbone arrangement (4), thus permitting intense emission in the aggregate state. In addition, the frontier molecular orbital energy and band gap calculated by density functional theory (DFT) are consistent with the experimental results. Compound 4 is cell-permeable: upon entering the live cells, the dye molecules can accumulate in the lysosomes and turn on the fluorescence.
研究领域:
材料科学
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纳米技术
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生物医学工程
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化学
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DOI
高影响因子
MOLECULES
·
2018
·Vol. 23
·期 9
·2290
·
IF 3.098
Liyan Liu,Yaohui Lei,Jianhui Zhang,Na Li,Fan Zhang,Huaqiao Wang,Feng He
Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (ФF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.Keywords:AIEE;multicolor;flavone;fluorophores;mitochondria
研究领域:
化学
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材料科学
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生物医学工程
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细胞生物学
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DOI
PubMed
高影响因子
MOLECULES
·
2020
·Vol. 25
·期 14
·3298
·
IF 3.267
Na Li,Liyan Liu,Huiqing Luo,Huaqiao Wang,Depo Yang,Feng He
Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction ofo-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (φF), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.Keywords:AIEE;flavanone;mitochondria;zebrafish
研究领域:
化学
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材料科学
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生物技术
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生物学
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DOI
PubMed
高影响因子
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
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2023
·
IF 4.3
Ping Yang,Pingping Xi,Xiaoqian Lu,Wenfei Zou,Chunhong Zheng,Shouzhi Pu
An aldehyde-containing diarylethene parent react with the benzothiazole acetonitrile which results in a photochromic aggregation-induced emission enhancement (AIEE) molecule. The title compound emits bright yellow fluorescence (λ em = 578 nm) in the solid state, which is contrast to many diarylethene derivatives having serious aggregation-caused quenching (ACQ). Further studies showed the title compound as colorimetric and fluorescent sensing cyanide sensor based on nucleophilic addition reaction with rapid response, excellent selectivity, and high sensitivity. Moreover, practical applications studied showed the title compound is convenient to detect for cyanide ion in food and actual water samples.
研究领域:
有机化学
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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
·
2013
·Vol. 3
·期 21
·7996-8002
·
IF 2.562
Qingkai Qi,Yifei Liu,Xiaofeng Fang,Yumo Zhang,Peng Chen,Yi Wang,Bing Yang,Bin Xu,Wenjing Tian,Sean Xiao-An Zhang
Two methoxy-substituted tetraphenylethylene (TPE) derivatives, tetra(4-methoxyphenyl)ethylene (TMOE) and tetra(3,4-dimethoxyphenyl)ethylene (TDMOE), were synthesized by McMurry reaction in high yields. The nearly centrosymmetric and natural propeller shape of TMOE and TDMOE excluded intermolecular effects, such as H or J-aggregation and π–π stacking, on their AIE (AIEE) and mechanofluorochromic performance. The crystal structures of TMOE and TDMOE, and theoretical calculations proved that their emission colours are determined by single molecular conjugation. These molecules were used to investigate pure conformational effects on molecular emissions. The spectral properties of these molecules in five environments of crystal(s), THF solution, THF–water binary solution, solidified THF and amorphous states, were investigated. The crystalline to amorphous phase transition by grinding resulted in good mechanofluorochromic performances with high quantum yields and distinguishable emission change, which was further explored as anti-counterfeiting inks on banknotes.
研究领域:
有机化学
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材料科学
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DOI
高影响因子
TETRAHEDRON
·
2018
·
IF 2.377
Yuqing Ma,Yuyang Zhang,Lin Kong,Jiaxiang Yang
Five quinoline derivatives containing different alkyl chains ( QLACn , n = 2, 4, 6, 8, 12) were synthesized to investigate the effect of alkyl chains on their photophysical properties. The fluorescent properties of the QLACn were affected by the alkyl chains, which indicated obvious blue-shifting trend and fluorescence emission are alkyl chains length-dependent by grinding-induced spectral shifts (Δλ MFC ). Longer alkyl-length revealed larger Δλ MFC . Powder X-ray diffraction (PXRD), scanning electron microscopy (SEM) and differential scanning calorimetry (DSC) measurements indicated that the transformation between microcrystalline and amorphous states upon external stimuli should be responsible for the observed reversible MFC behavior.
研究领域:
材料科学
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光物理学
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DOI
高影响因子
MOLECULES
·
2023
·Vol. 28
·期 12
·4592
·
IF 4.6
Tingting Jin,Na Li,Yi Wu,Ying He,Depo Yang,Feng He
Nobiletin is a natural product with multiple physiological activities and is the main ingredient ofPericarpium Citri Reticulatae. We successfully discovered that nobiletin exhibits aggregation induced emission enhancement (AIEE) properties and it has significant advantages such as a large Stokes shift, good stability and excellent biocompatibility. The increase in methoxy groups endows nobiletin a greater fat-solubility, bioavailability and transport rate than the corresponding unmethoxylated flavones. Ulteriorly, cells and zebrafish were used to explore the application of nobiletin in biological imaging. It emits fluorescence in cells and is specifically targeted at mitochondria. Moreover, it has a noteworthy affinity for the digestive system and liver of zebrafish. Due to the unique AIEE phenomenon and stable optical properties of nobiletin, it paves the way for discovering, modifying and synthesizing more molecules with AIEE characteristics. Furthermore, it has a great prospect with regard to imaging cells and cellular substructures, such as mitochondria, which play crucial roles in cell metabolism and death. Indeed, three-dimensional real-time imaging in zebrafish provides a dynamic and visual tool for studying the absorption, distribution, metabolism and excretion of drugs. In this article, more directions and inspiration can be presented for the exploration of non-invasive pharmacokinetic research and intuitive drug pathways or mechanisms.Keywords:nobiletin;AIEE;zebrafish;visual pharmacokinetics
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PubMed
高影响因子
Methods and Applications in Fluorescence
·
2022
·Vol. 10
·期 3
·035004
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IF 3.849
Linli Xiong,Yong Zheng,Haibo Wang,Jiangyang Yan,Xuguang Huang,Hongyun Meng,Chunhua Tan
A novel fluorescence sensor for successive detection of Cu2+ and Fe3+ based on anti-B18H22 derivative which possesses 5-hydroxyisoquinoline as an ionophore was synthesized via a one-pot and its structure and photophysical properties were characterized by NMR, HRMS, FTIR, UV–vis, PL and theoretical calculation. The fluorophore displays two emission peaks at 460 nm and 670 nm in THF solution coming from the emission of the locally excited state and intramolecular charge transfer fluorescence, respectively. The complex exhibited obvious aggregation-induced emission enhancement (AIEE) characteristics in THF/H2O solution by increasing the aqueous concentration from 70% to 95%. The AIEE molecules showed a high selectivity towards Cu2+ over other metal ions by forming a 2:1 metal-to-ligand complex in THF/H2O (fw = 20%) solution, the fluorescence intensity increased as a linear function of the Cu2+ concentration at 460 nm due to the inhibition of PET effect. The fluorescent emission was quenched linearly by the addition of Fe3+, which provides a method for successive determination of Cu2+ and Fe3+ based on 'off-on-off' fluorescence of the fluorescent. The detection limit of Cu2+ and Fe3+ was 5.7 × 10−6 M and 7.2 × 10−5 M respectively. Morever, a rapid identification of Cu2+ in the aqueous solution by naked eyes can be realized. In addition, the molecules were pH-sensitive, the fluorescence quenching can be observed in strongly alkaline environment. The method has been applied to the determination of copper ions in water samples with satisfactory results.
研究领域:
化学
·
材料科学
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DOI
高影响因子
JOURNAL OF FLUORESCENCE
·
2024
·
IF 2.6
Li Maomao,Zhu Wenjie,Song Dongdong,Liang Zuoqin,Ye Changqing
Latent fingerprints (LFPs) is one of the most important physical evidence in the criminal scene, playing an important role in forensic investigations. Therefore, developing highly sensitive and convenient materials for the visualization of LFPs is of great significance. We designed and synthesized an organic fluorescent molecule TP-PH with aggregation-induced enhanced emission (AIEE) activity. By simply soaking, blue fluorescent images with high contrast and resolution are readily developed on various surfaces including tinfoil, steel, glass and plastic. Remarkably, LFPs can be visualized within 5 min including the first-, second- and tertiary-level details. In addition, TP-PH exhibits interesting photoactivated fluorescence enhancement properties. Under irradiation of 365 nm UV light with a power density of 382 mW/cm 2 , the fluorescence quantum yield displays approximately 21.5-fold enhancement. Mechanism studies reveals that the photoactivated fluorescence is attributed to the irreversible cyclodehydrogenation reactions under UV irradiation. This work provides a guideline for the design of multifunctional AIEE fluorescent materials.
研究领域:
材料科学
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法医学
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有机化学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2021
·Vol. 22
·期 16
·8949
·
IF 5.924
Huiqing Luo,Na Li,Liyan Liu,Huaqiao Wang,Feng He
Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted increasing interest in recent years. On the basis of our previous research, we successfully designed and synthesized eleven chalcones. Through an optical performance experiment, we confirmed that compounds1–6had obvious AIEE properties. As these AIEE molecules had excellent fluorescence properties and a large Stokes shift, we studied their application in living cell imaging, and the results showed that these compounds had low cytotoxicity and good biocompatibility at the experimental concentrations. More importantly, they could specifically label mitochondria. Subsequently, we selected zebrafish as experimental animals to explore the possibilities of these compounds in animal imaging. The fluorescence imaging of zebrafish showed that these AIEE molecules can enter the embryo and can be targeted to aggregate in the digestive tract, which provides a strong foundation for their practical application in the field of biological imaging. Compared with traditional fluorophores, these AIEE molecules have the advantages of possessing a small molecular weight and high flexibility. Therefore, they have excellent application prospects in the field of biological imaging. In addition, the findings of this study have very positive practical significance for the discovery of more AIEE molecules.Keywords:AIEE;chalcone;mitochondria;zebrafish
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PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2023
·Vol. 24
·期 12
·10183
·
IF 5.6
Yi Wu,Ying He,Huiqing Luo,Tingting Jin,Feng He
In recent years, aggregation-induced emission enhancement (AIEE) molecules have shown great potential for applications in the fields of bio-detection, imaging, optoelectronic devices, and chemical sensing. Based on our previous studies, we investigated the fluorescence properties of six flavonoids and confirmed that compounds1–3have good aggregation-induced emission enhancement (AIEE) properties through a series of spectroscopic experiments. Compounds with AIEE properties have addressed the limitation imposed by the aggregation-caused quenching (ACQ) of classic organic dyes owing to their strong fluorescence emission and high quantum yield. Based on their excellent fluorescence properties, we evaluated their performance in the cell and we found that they could label mitochondria specifically by comparing their Pearson correlation coefficients (R) with Mito Tracker Red and Lyso-Tracker Red. This suggests their future application in mitochondrial imaging. Furthermore, studies of uptake and distribution characterization in 48 hpf zebrafish larvae revealed their potential for monitoring real-time drug behavior. The uptake of compounds by larvae varies significantly across different time cycles (between uptake and utilization in the tissue). This observation has important implications for the development of visualization techniques for pharmacokinetic processes and can enable real-time feedback. More interestingly, according to the data presented, tested compounds aggregated in the liver and intestine of 168 hpf larvae. This finding suggests that they could potentially be used for monitoring and diagnosing liver and intestinal diseases.Keywords:AIEE;flavones;mitochondria;zebrafish;uptake;distribution
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PubMed
高影响因子
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