Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Assembly of 1H-isoindole derivatives by selective carbon-nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging.

ABSTRACT: A novel strategy has been established to assemble a series of single (Z)- or (E)-1H-isoindole derivatives through selectively and sequentially activating carbon-nitrogen triple bonds in a multicomponent system containing various nucleophilic and electrophilic sites. The reaction provides efficient access to structurally unique fluorophores with aggregation-induced emission characteristics. These new fluorophores show fluorescence wavelengths and efficiencies that can be modulated and have excellent potential to specifically light up lipid droplets (LDs) in living cells with bright fluorescence, low cytotoxicity and better photostability than commercially available LD-specific dyes.

SUBMITTER: He D

PROVIDER: S-EPMC6677114 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Assembly of 1H-isoindole derivatives by selective carbon-nitrogen triple bond activation: access to aggregation-induced emission fluorophores for lipid droplet imaging.

He Dandan D Zhuang Zeyan Z Wang Xu X Li Jiawei J Li Jianxiao J Wu Wanqing W Zhao Zujin Z Jiang Huanfeng H Tang Ben Zhong BZ

Chemical science 20190612 29

A novel strategy has been established to assemble a series of single (Z)- or (E)-1H-isoindole derivatives through selectively and sequentially activating carbon-nitrogen triple bonds in a multicomponent system containing various nucleophilic and electrophilic sites. The reaction provides efficient access to structurally unique fluorophores with aggregation-induced emission characteristics. These new fluorophores show fluorescence wavelengths and efficiencies that can be modu ...[more]

PMID: 31588275

Similar Datasets

Organic solid fluorophores regulated by subtle structure modification: color-tunable and aggregation-induced emission.

Project description:Organic solid fluorophores with a tunable emission color have been widely applied in multiple areas. However, rational design and efficient crafting of these fluorophores from a simple core skeleton is still a formidable challenge because of the undesirable concentration quenching emission effect. Herein, we present the development of two series of organic solid fluorophores based on a backbone of p-bis(2,2-dicyanovinyl)benzene. Notably, the introduction of either non-aromatic or aromatic substituents provides fluorophores with a tunable emission color. Moreover, the fluorophores with aromatic substituents exhibit additional unique optical phenomena, such as aggregation-induced emission, polymorphism-dependent emission, and reversible mechanochromic luminescence.

| S-EPMC5351801 | biostudies-literature

NIR-II and visible fluorescence hybrid imaging-guided surgery via aggregation-induced emission fluorophores cocktails.

Project description:Fluorescence imaging-guided surgery is one of important techniques to realize precision surgery. Although second near-infrared window (NIR-II) fluorescence imaging has the advantages of high resolution and large penetration depth in surgical navigation, its major drawback is that NIR-II images cannot be detected by our naked eyes, which demands a high hand-eye coordination for surgeons and increases the surgical difficulty. On the contrary, visible fluorescence can be observed by our naked eyes but has poor penetration. Here, we firstly propose a kind of NIR-II and visible fluorescence hybrid navigation surgery assisted via a cocktail of aggregation-induced emission nanoparticles (AIE NPs). NIR-II imaging helps to locate deep targeted tissues and judge the residual, and visible fluorescence offers an easily surgical navigation. We apply this hybrid navigation mode in different animals and systems, and verify that it can accelerate surgical process and compatible with a visible fluorescence endoscopy. To deepen the understanding of lymph node (LN) labelling, the distribution of NPs in LNs after local administration is initially analyzed by NIR-II fluorescence wide-filed microscopy, and two fates of the NPs are summarized. An alternative strategy which combines indocyanine green and berberine is also reported as a compromise for rapidly clinical translation.

| S-EPMC9424606 | biostudies-literature

Solvent polarity driven helicity inversion and circularly polarized luminescence in chiral aggregation induced emission fluorophores.

Project description:Development of functional materials capable of exhibiting chirality tunable circularly polarized luminescence (CPL) is currently in high demand for potential technological applications. Herein we demonstrate the formation of both left- and right-handed fluorescent helical superstructures from each enantiomer of a chiral tetraphenylethylene derivative through judicious choice of the solution processing conditions. Interestingly, both the aggregation induced emission active enantiomers exhibit handedness inversion of their supramolecular helical assemblies just by varying the solution polarity without any change in their molecular chirality. The resulting helical supramolecular aggregates from each enantiomer are capable of emitting circularly polarized light, thus enabling both right- and left-handed CPL from a single chiral material. The left- and right-handed supramolecular helical aggregates in the dried films have been characterized using spectroscopy, scanning electron microscopy, and transmission electron microscopy techniques. These new chiral aggregation induced emission compounds could find applications in devices where CPL of opposite handedness is required from the same material and would facilitate our understanding of the formation of helical assemblies with switchable supramolecular chirality.

| S-EPMC8162095 | biostudies-literature

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

Project description: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.

| S-EPMC7397278 | biostudies-literature

2-Hydroxybenzophenone Derivatives: ESIPT Fluorophores Based on Switchable Intramolecular Hydrogen Bonds and Excitation Energy-Dependent Emission.

Project description:In this work, a new series of 2-hydroxybenzophenone (BPOH) derivatives, BPOH-TPA, BPOH-PhCz, and BPOH-SF substituting with different electron-donating groups are designed and synthesized. Dual-emission spectra are observed in solutions indicating their excited-state intramolecular proton transfer (ESIPT) character. In solid states, all compounds exhibit a broad emission spectrum when excited at low excitation energy, deriving from the enol-type form stabilized by intramolecular hydrogen bonds. Compound BPOH-TPA shows a clear excitation wavelength dependence. However, such behavior is absent in BPOH-PhCz and BPOH-SF, as the rigid and weaker donor moieties may restrict this process. Furthermore, by increasing the excitation energy, dual emission with a high-energy band ranging from 550 to 582 nm and a low-energy band ranging from 625 to 638 nm is obtained in all three molecules. The photophysical studies and single-crystal analyses are performed to further illustrate the excitation-dependent emission. Higher excitation energies can promote more excitons to keto forms via ESIPT, giving a stronger redshifted emission. BPOH-TPA with a stronger donor strength exhibits an obvious color change gradually from yellow to orange-red with the increasing excitation power from 1 to 15 mW/cm2. This study provides a novel example of ESIPT materials with tunable emission colors.

| S-EPMC8560898 | biostudies-literature

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

Project description: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.

| S-EPMC6225312 | biostudies-literature

Facile scission of isonitrile carbon-nitrogen triple bond using a diborane(4) reagent.

Project description:Transition metal reagents and catalysts are generally effective to cleave all three bonds (one σ and two π) in a triple bond despite its high bonding energy. Recently, chemistry of single-bond cleavage by using main-group element compounds is rapidly being developed in the absence of transition metals. However, the cleavage of a triple bond using non-transition-metal compounds is less explored. Here we report that an unsymmetrical diborane(4) compound could react with carbon monoxide and tert-butyl isonitrile at room temperature. In the latter case, the carbon-nitrogen triple bond was completely cleaved in the absence of transition metal as confirmed by X-ray crystallographic analysis, (13)C NMR spectroscopy with (13)C labelling and DFT calculations. The DFT calculations also revealed the detailed reaction mechanism and indicated that the key for the carbon-nitrogen triple-bond cleavage could be attributed to the presence of nucleophilic nitrogen atom in one of the intermediates.

| S-EPMC4083417 | biostudies-literature

Thiophene-containing tetraphenylethene derivatives with different aggregation-induced emission (AIE) and mechanofluorochromic characteristics.

Project description:Four thiophene-containing tetraphenylethene derivatives were successfully synthesized and characterized. All these highly fluorescent compounds showed typical aggregation-induced emission (AIE) characteristics and emitted different fluorescence colors including blue-green, green, yellow and orange in the aggregation state. In addition, these luminogens also exhibited various mechanofluorochromic phenomena.

| S-EPMC9069574 | biostudies-literature

Practical Design of 3,6-Di-tert-butyldiphenyldibenzofulvene Derivatives with Enhanced Aggregation-Induced Emission

Project description:Diphenyldibenzofulvene derivatives consisting of an aromatic tert-butyl-substituted fluorene stator and different rotors

| S-EPMC9903363 | biostudies-literature

Probing the Aggregation and Signaling Behavior of Some Twisted 9,9'-Bianthryl Derivatives: Observation of Aggregation-Induced Blue-Shifted Emission.

Project description:With an aim to understand the photophysical behavior of twisted organic fluorescent molecules in their aggregated state, two twisted biaryl molecules, namely, 9,9'-bianthryl and 10,10'-dicyano-9,9'-bianthryl, have been synthesized and characterized by conventional spectroscopic methods. To understand the role of C-C bond twisting on the photophysical response of biaryl aggregates, monoaryl counterparts (anthracene and 9-anthracenecarbonitrile) of the biaryl systems are also investigated. Photophysical behaviors of these systems along with their monoaryl counterpart are investigated in both solution and aggregated state. Investigations reveal that fluorescence spectra of the biaryl compounds show blue-shifted emission upon aggregation. Interestingly, no blue shift of the emission has been observed for monoaryl aggregates. Photophysical data of biaryl systems compared to monoaryl unit reveal that change in geometry, during self-assembly process, disfavors the formation of charge-transfer state, which eventually causes blue shift in the emission upon aggregation. In addition to this, potential of these systems toward signaling of nitroaromatic explosive has also been explored. Among all of the nitroaromatics, the highest fluorescence quenching is observed for nitrophenols (say picric acid (PA)). The investigation also reveals that compared to monoaryl systems, biaryl systems are more responsive to fluorescence quenching by nitroaromatics. Perrin's model of quenching sphere action has been attributed to nitrophenol (PA) selective signaling behavior of biaryl systems.

| S-EPMC6644316 | biostudies-literature