Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging

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.

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Nopinone-based aggregation-induced emission (AIE)-active difluoroboron β-diketonate complex: photophysical, electrochemical and electroluminescence properties

RSC Advances ◽

10.1039/c8ra05031g ◽

2018 ◽

Vol 8 (52) ◽

pp. 30055-30060 ◽

Cited By ~ 2

Author(s):

Qian Jiang ◽

Mingguang Zhang ◽

Zhonglong Wang ◽

Jie Song ◽

Yiqin Yang ◽

...

Keyword(s):

Green Light ◽

Quantum Yields ◽

Aggregation Induced Emission ◽

Fluorescence Quantum Yields ◽

Absolute Fluorescence

Four difluoroboron (BF2) β-diketonate nopinone complexes 3a–3d which exhibited typical AIE property were synthesized. Owing to high absolute fluorescence quantum yields of 3b, EL device based on 3b was fabricated, which exhibits a blue-green light.

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Efficient and thermally stable non-doped red OLEDs based on a “bird-like” donor–acceptor fluorophore with aggregation induced emission enhancement and intramolecular charge transfer

Journal of Materials Chemistry C ◽

10.1039/c7tc02253k ◽

2017 ◽

Vol 5 (30) ◽

pp. 7436-7440 ◽

Cited By ~ 12

Author(s):

Ezhakudiyan Ravindran ◽

Narayanasastri Somanathan

Keyword(s):

Charge Transfer ◽

Rational Design ◽

Intramolecular Charge Transfer ◽

Thermally Stable ◽

Aggregation Induced Emission ◽

Emission Enhancement ◽

Donor Acceptor ◽

Red Oleds

The rational design of an efficient and thermally stable non-doped red fluorophore material with tunable AIEE and ICT characteristics triggers enhanced OLED performances.

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Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

International Journal of Molecular Sciences ◽

10.3390/ijms22168949 ◽

2021 ◽

Vol 22 (16) ◽

pp. 8949

Author(s):

Huiqing Luo ◽

Na Li ◽

Liyan Liu ◽

Huaqiao Wang ◽

Feng He

Keyword(s):

Stokes Shift ◽

Biological Imaging ◽

Practical Significance ◽

Small Molecular Weight ◽

Emission Enhancement ◽

Animal Imaging ◽

Low Cytotoxicity ◽

High Flexibility ◽

Living Cell Imaging

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 compounds 1–6 had 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.

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Chiral Pentaphenylpyrrole Derivatives with Aggregation-Induced Emission Enhancement and Aggregation Induced Circular Dichroism and Their Helical Self-assembly

E3S Web of Conferences ◽

10.1051/e3sconf/202126702012 ◽

2021 ◽

Vol 267 ◽

pp. 02012

Author(s):

Yuanyuan Wang ◽

Longlong Zhang ◽

Junge Zhi

Keyword(s):

Circular Dichroism ◽

Self Assembly ◽

Nano Particles ◽

Mixed Solution ◽

Induced Circular Dichroism ◽

Aggregation Induced Emission ◽

Water Fraction ◽

Chiral Compounds ◽

Emission Enhancement ◽

Circular Dichroïsm

A pair of enantiomers (S)-P5PdiAM and (R)-P5PdiAM containing two chiral substituents, and their raceme rac-P5PdiAM were synthesized by introducing (R)-/(S)- or racemic 1-phenylethylamine into 1-biphenyl-2,3,4,5-tetraphenylpyrrole. The target compounds all show weak aggregation-induced emission enhancement (AIEE) characteristics in the DMSO/H2O mixed system, indicating that the introduction of chirality hardly affect the photophysical properties of the compound. In addition, the chiral compounds (S)-P5PdiAM and (R)-P5PdiAM show strong circular dichroism (CD) signals in THF/H2O mixed solution with a water fraction of 70%, that is, they exhibit aggregation-induced circular dichroism characteristics (AICD). Because the aggregates of (S)-P5PdiAM and (R)-P5PdiAM emit weakly, there is no circularly polarized luminescence (CPL) signals upon aggregation. The chiral compounds (S)-P5PdiAM and (R)-P5PdiAM can self-assemble to form helical nanofibers in a THF/H2O mixture with a water fraction of 70%, while the racemic rac-P5PdiAM assembled to form nano-particles, indicating that chiral substituents have a great influence on the self-assembly and the morphologies of the nano-aggregates.

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Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.262 ◽

2019 ◽

Vol 15 ◽

pp. 2684-2703 ◽

Cited By ~ 1

Author(s):

Natascha Breuer ◽

Irina Gruber ◽

Christoph Janiak ◽

Thomas J J Müller

Keyword(s):

Solid State ◽

Michael Addition ◽

Photophysical Properties ◽

Ethyl Cyanoacetate ◽

Product Formation ◽

Quantum Yields ◽

Substitution Pattern ◽

Fluorescence Quantum Yields ◽

Emission Enhancement ◽

Donor Acceptor

Starting from substituted alkynones, α-pyrones and/or 1H-pyridines were generated in a Michael addition–cyclocondensation with ethyl cyanoacetate. The peculiar product formation depends on the reaction conditions as well as on the electronic substitution pattern of the alkynone. While electron-donating groups furnish α-pyrones as main products, electron-withdrawing groups predominantly give the corresponding 1H-pyridines. Both heterocycle classes fluoresce in solution and in the solid state. In particular, dimethylamino-substituted α-pyrones, as donor–acceptor systems, display remarkable photophysical properties, such as strongly red-shifted absorption and emission maxima with daylight fluorescence and fluorescence quantum yields up to 99% in solution and around 11% in the solid state, as well as pronounced emission solvatochromism. Also a donor-substituted α-pyrone shows pronounced aggregation-induced emission enhancement.

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Influence of molecular weight on the aggregation-induced emission enhancement and spectral stability of vinyl polymers containing the fluorescent 2,4,6-triphenylpyridine pendant groups

Journal of Materials Chemistry ◽

10.1039/c2jm30455d ◽

2012 ◽

Vol 22 (19) ◽

pp. 9546 ◽

Cited By ~ 17

Author(s):

Chung Tin Lai ◽

Jin Long Hong

Keyword(s):

Molecular Weight ◽

Spectral Stability ◽

Aggregation Induced Emission ◽

Vinyl Polymers ◽

Emission Enhancement

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Abnormally aggregation-induced emissions observed from hydrogen- and silyl-substituted siloles

Main Group Metal Chemistry ◽

10.1515/mgmc-2020-0015 ◽

2020 ◽

Vol 43 (1) ◽

pp. 125-131

Author(s):

Zhengang Han ◽

Kefeng Xie

Keyword(s):

Hydrogen Atom ◽

Theoretical Calculations ◽

Quantum Yields ◽

Aggregation Induced Emission ◽

Fluorescence Quantum Yields ◽

High Fluorescence ◽

First Time

AbstractSilacyclopentadienes (siloles) are currently of great interest because of their intriguing aggregation-induced emission (AIE) characteristics. In this work, abnormally AIE phenomena were observed from silyl- and hydrogen-substituted siloles respectively. We propose silyl-substituent and hydrogen atom effects to explain this via both experiments and theoretical calculations. It was discovered that trimethylsilyl substituents destroyed the p-interactions with the silole core and resulted in the non-fluorescence. Additionally, 1-chloro-1-H-2,3,4,5-tetraphenylsilole featuring strong fluorescences in both solid and solution states with high fluorescence quantum yields represents a new potential photoelectric material. This work not only reports the silole with strong fluorescences in both solid and solution states for the first time but also contributs to enrich the AIE research of siloles.

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Heavy Atom Effect on Metallole Nanoaggregates and Their Explosive Sensing Applications

Journal of Nanoscience and Nanotechnology ◽

10.1166/jnn.2020.17638 ◽

2020 ◽

Vol 20 (9) ◽

pp. 5599-5603

Author(s):

Bomina Shin ◽

Honglae Sohn

Keyword(s):

Optical Properties ◽

Central Atom ◽

Heavy Atom ◽

Quantum Yields ◽

Aggregation Induced Emission ◽

Sensing Applications ◽

Emission Enhancement ◽

Atom Effect ◽

Absolute Quantum ◽

Explosive Sensing

Electronic and optical properties of metallole nanoaggregates (M = Ge and Sn) were investigated. Amplified photoluminescence (PL) properties, absolute quantum yields (QY), and critical aggregation concentrations for the metallole nanoaggregates were measured. The an aggregation-induced emission enhancement (AIEE) property decreases as the central atom becomes heavier in the metallole ring. Detection of TNT was achieved by the quenching PL of the metallole nanoaggregates. A linear Stern–Volmer relationship was observed for the detection of TNT.

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Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.164 ◽

2019 ◽

Vol 15 ◽

pp. 1601-1611 ◽

Cited By ~ 4

Author(s):

Guojuan Li ◽

Chunying Fan ◽

Guo Cheng ◽

Wanhua Wu ◽

Cheng Yang

Keyword(s):

Quantum Yield ◽

Click Reaction ◽

Photophysical Properties ◽

High Yield ◽

Mixed Solution ◽

Aggregation Induced Emission ◽

Emission Enhancement ◽

Emission Quenching ◽

High Fluorescence ◽

Induced Aggregation

Planar chiral pillar[5]arene derivatives (P5A-DPA and P5A-Py) bearing bulky fluorophores were obtained in high yield by click reaction. The photophysical properties of both compounds were investigated in detail. P5A-DPA with two 9,10-diphenylanthracene (DPA) pigments grafted on the pillar[5]arene showed a high fluorescence quantum yield of 89.5%. This is comparable to the monomer DPA-6, while P5A-Py with two perylene (Py) pigments grafted on the pillar[5]arene showed a significantly reduced quantum yield of 46.4% vs 78.2% for the monomer Py-6. The oxygen-through-annulus rotation of the phenolic units was inhibited for both compounds due to the bulky chromophore introduced, and the resolution of the enantiomers was achieved due to the bulky size of the fluorophores. The absolute configuration of the enantiomers was determined by circular dichroism (CD) spectra. The solvent-induced aggregation behavior was investigated with the enantiopure P5A-DPA and P5A-Py. It was found that the CD signals were enhanced by aggregation. P5A-DPA showed aggregation-induced emission enhancement, while P5A-Py showed aggregation-induced emission quenching, accompanied by excimer emission when aggregating in water and THF mixed solution.

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