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

2019 ◽  
Vol 15 ◽  
pp. 1601-1611 ◽  
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.

scholarly journals Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3298
Author(s):  
Na Li ◽  
Liyan Liu ◽  
Huiqing Luo ◽  
Huaqiao Wang ◽  
Depo Yang ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Fluorescence Quantum Yield ◽  
Fluorescent Dyes ◽  
Fluorescence Emission ◽  
In Vivo Studies ◽  
Aggregation Induced Emission ◽  
Emission Enhancement ◽  
High Fluorescence ◽  
Potential Use

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 of o-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.

scholarly journals Achieving remarkable and reversible mechanochromism from a bright ionic AIEgen with high specificity for mitochondrial imaging and secondary aggregation emission enhancement for long-term tracking of tumors

2020 ◽  
Vol 4 (3) ◽  
pp. 941-949 ◽  
Author(s):  
Xinzhe Yang ◽  
Qian Wang ◽  
Peiyu Hu ◽  
Chao Xu ◽  
Wenjing Guo ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Cancer Cells ◽  
Fluorescence Quantum Yield ◽  
High Specificity ◽  
Emission Enhancement ◽  
High Fluorescence ◽  
High Fluorescence Quantum Yield

An ionic AIEgen with high fluorescence quantum yield shows remarkable and reversible mechanochromism as well as excellent mitochondrial imaging of cancer cells and long-term tracking of tumors.

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

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.

scholarly journals Photophysical Challenges and Antenna Effect Between Click Reaction-based Bodipy Derivatives Manufactured From Knorr Pyrrole

2021 ◽  
Author(s):  
ahmed nuri kursunlu ◽  
Akif Kagan Yilmaz ◽  
Elif Bastug ◽  
Ersin Guler
Keyword(s):  
Energy Transfer ◽  
Quantum Yield ◽  
Absorption Coefficient ◽  
Organic Solvents ◽  
Click Reaction ◽  
Photophysical Properties ◽  
Molar Absorption Coefficient ◽  
Antenna Effect ◽  
Preliminary Study

Abstract In this paper, a series of click reaction-based Bodipy derivatives have been synthesized as part of a preliminary study. Following the characterization of the four challenger molecules, the photophysical properties (absorption, emission, excitation, molar absorption coefficient, quantum yield, etc.) were examined in various organic solvents. The results showed that the energy transfer from the Bodipy cores to other moieties was calculated between 71% and 93% depending on different π-electron configurations and chromophore groups.

Aggregation-induced emission enhancement (AIEE) of N,N′-Bis(Salicylidene)-p-Phenylenediamine Schiff base: Synthesis, photophysical properties and its DFT studies

2019 ◽  
Vol 210 ◽  
pp. 493-500 ◽  
Author(s):  
Nichakan Miengmern ◽  
Amonchat Koonwong ◽  
Suwannee Sriyab ◽  
Anwaraporn Suramitr ◽  
Rungtiva P. Poo-arporn ◽  
...  
Keyword(s):  
Schiff Base ◽  
Photophysical Properties ◽  
Dft Studies ◽  
Aggregation Induced Emission ◽  
Emission Enhancement

scholarly journals Chiroptical property enhancement of chiral Eu(III) complex upon association with DNA-CTMA

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Haruki Minami ◽  
Natsumi Itamoto ◽  
Wataru Watanabe ◽  
Ziying Li ◽  
Kazuki Nakamura ◽  
...  
Keyword(s):  
Structural Change ◽  
Quantum Yield ◽  
Functional Properties ◽  
Photophysical Properties ◽  
Luminescent Properties ◽  
Dna Molecule ◽  
Emission Enhancement ◽  
Chiroptical Property ◽  
Potential Applications ◽  
Sensitization Efficiency

Abstract DNA-based materials have attracted much attention due to their unique photo-functional properties and potential applications in various fields such as luminescent and biological systems, nanodevices, etc. In this study, the photophysical properties of a chiral Eu(III) complex, namely (Eu(D-facam)3), within DNA films were extensively investigated. The enhancement of photoluminescence (more than 25-folds increase of luminescence quantum yield) and degree of circularly polarization in luminescence (glum = − 0.6) was observed upon interaction with DNA. Various photophysical analyses suggested that the emission enhancement was mainly due to an increase of the sensitization efficiency (high ηsens) from the ligands to Eu(III) and suppression of the vibrational deactivation upon immobilization onto the DNA molecule. From CD and VCD measurements, it was suggested that the coordination structure of Eu(D-facam)3 was affected by the interaction with DNA, suggesting that the structural change of Eu(D-facam)3 contributed to the improvement of its luminescent properties.

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

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2290
Author(s):  
Liyan Liu ◽  
Yaohui Lei ◽  
Jianhui Zhang ◽  
Na Li ◽  
Fan Zhang ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Rational Design ◽  
Quantum Yields ◽  
Mixed Solution ◽  
Small Molecular Weight ◽  
Aggregation Induced Emission ◽  
Fluorescence Quantum Yields ◽  
Emission Enhancement ◽  
Low Cytotoxicity ◽  
Further Development

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.

Glutathione modified carbon-dots: from aggregation-induced emission enhancement properties to a “turn-on” sensing of temperature/Fe3+ ions in cells

2016 ◽  
Vol 3 (4) ◽  
pp. 514-522 ◽  
Author(s):  
Chuanxi Wang ◽  
Kaili Jiang ◽  
Zhenzhu Xu ◽  
Huihui Lin ◽  
Chi Zhang
Keyword(s):  
Aqueous Solution ◽  
Carbon Dots ◽  
Aggregation Induced Emission ◽  
Turn On ◽  
Good Dispersion ◽  
Emission Enhancement ◽  
High Fluorescence ◽  
In Cells

Glutathione stabilized carbon dots show good dispersion, high fluorescence and aggregation-induced emission enhancement properties which could be used as a “turn-on” chemosensor for detecting temperature and Fe3+ in aqueous solution and cells.

scholarly journals Multicomponent Synthesis of Luminescent Iminoboronates

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 6039
Author(s):  
Samuel Guieu ◽  
Cátia I. C. Esteves ◽  
João Rocha ◽  
Artur M. S. Silva
Keyword(s):  
Crystal Structures ◽  
Multicomponent Reaction ◽  
Anthranilic Acid ◽  
Boronic Acid ◽  
Photophysical Properties ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Aggregation Induced Emission ◽  
Emission Enhancement ◽  
Diluted Solution

A family of iminoboronates was prepared through a one-pot multicomponent reaction, starting from boronic acid, anthranilic acid, and different salicylaldehydes. Their synthesis was straightforward and the complexes were obtained in good to excellent yields. Their photophysical properties were assessed in a diluted solution, and the complexes proved to be faintly luminescent. These chelates demonstrated remarkable Aggregation-Induced Emission Enhancement, which was rationalized using crystal structures.

Synthesis, properties and photo-responsive behavior of luminescent side chain polymers containing D–π-A α-cyanostilbene units

2019 ◽  
Vol 10 (21) ◽  
pp. 2706-2715 ◽  
Author(s):  
Yongjie Yuan ◽  
Lifang He ◽  
Jindi Li ◽  
Hailiang Zhang
Keyword(s):  
Quantum Yield ◽  
Fluorescence Quantum Yield ◽  
Side Chain ◽  
Aggregation Induced Emission ◽  
High Solid ◽  
Emission Enhancement ◽  
Synthesis Properties ◽  
Responsive Behavior ◽  
Solid Fluorescence

A series of luminescent side chain polymers with aggregation-induced emission enhancement characteristics, high solid fluorescence quantum yield, and reversible fluorescence photo-responsive properties were prepared.

Sign in / Sign up

Export Citation Format

Share Document