Browse
Submit Data
Databases
API
Help

Dataset Information

34 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Achieving Molecular Fluorescent Conversion from Aggregation-Caused Quenching to Aggregation-Induced Emission by Positional Isomerization.

ABSTRACT: In this work, we synthesized a pair of positional isomers by attaching a small electron-donating pyrrolidinyl group at ortho- and para-positions of a conjugated core. These isomers exhibited totally different fluorescent properties. PDB2 exhibited obvious aggregation-induced emission properties. In contrast, PDB4 showed the traditional aggregation-caused quenching effect. Their different fluorescent properties were investigated by absorption spectroscopy, fluorescence spectroscopy, density functional theory calculations and single-crystal structural analysis. These results indicated that the substituent position of the pyrrolidinyl groups affects the twisted degree of the isomers, which further induces different molecular packing modes, thus resulting in different fluorescent properties of these two isomers. This molecular design concept provided a new accurate strategy for designing new aggregation-induced emission luminogens.

SUBMITTER: Wang X

PROVIDER: S-EPMC8747061 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Molecular design of near-infrared fluorescent Pdots for tumor targeting: aggregation-induced emission versus anti-aggregation-caused quenching.

Project description:Semiconducting polymer dots (Pdots) have recently emerged as a new type of ultrabright fluorescent probe that has been proved to be very useful for biomedical imaging. However, Pdots often suffer from serious fluorescence aggregation-caused quenching (ACQ) especially for near-infrared (NIR) fluorescent Pdots. This article compared two strategies to overcome the ACQ effect in near-infrared emissive Pdot systems: aggregation-induced emission (AIE) and anti-aggregation-caused quenching (anti-ACQ). The results show that the anti-ACQ platform outperforms the AIE system. The fluorescence quantum yield of anti-ACQ-based Pdots can be over 50% and the average per-particle brightness of the Pdots is about 5 times higher than that of the commercially available quantum dots. To help understand why the monomer conformations could greatly affect the optical properties of Pdots, molecular dynamics simulations were performed for the first time in such complicated Pdot systems. To demonstrate applications for in vivo fluorescence imaging, both microangiography imaging on living zebrafish embryos and specific tumor targeting on mice were performed. We anticipate that these studies will pave the way for the design of new highly fluorescent Pdot systems.

| S-EPMC6333168 | biostudies-literature

An arch-bridge-type fluorophore for bridging the gap between aggregation-caused quenching (ACQ) and aggregation-induced emission (AIE).

Project description:Solution and solid dual photoluminescence (PL) molecules fill the substantial gap between ACQ and AIE molecules to explore the mechanism of molecular luminescence in greater detail and to facilitate practical applications. A unique arch-bridge-like thiazolo[5,4-b]thieno[3,2-e]pyridine moiety is obtained as a stator after the rigidification of rotor 1 by intramolecular H-bonding of ortho -OH or -NH2 to afford two classes of solid and solution dual PL molecules. As a typical example, DF5 is dual PL active. Moreover, the large Stokes shift with high dual PL efficiency (?F up to 51% in the solid state, 80% in DMF, 74% in DMSO, and 100% in water), together with the good thermal stability (Tm > 200 °C and T05 > 200 °C), make it more practical for promising optoelectronic and biological applications.

| S-EPMC6016330 | biostudies-other

Reducing aggregation caused quenching effect through co-assembly of PAH chromophores and molecular barriers.

Project description:The features of well-conjugated and planar aromatic structures make ?-conjugated luminescent materials suffer from aggregation caused quenching (ACQ) effect when used in solid or aggregated states, which greatly impedes their applications in optoelectronic devices and biological applications. Herein, we reduce the ACQ effect by demonstrating a facile and low cost method to co-assemble polycyclic aromatic hydrocarbon (PAH) chromophores and octafluoronaphthalene together. Significantly, the solid photoluminescence quantum yield (PLQYs) for the as-resulted four micro/nanococrystals are enhanced by 254%, 235%, 474 and 582%, respectively. Protection from hydrophilic polymer chains (P123 (PEO20-PPO70-PEO20)) endows the cocrystals with superb dispersibility in water. More importantly, profiting from the above-mentioned highly improved properties, nano-cocrystals present good biocompatibility and considerable cell imaging performance. This research provides a simple method to enhance the emission, biocompatibility and cellular permeability of common chromophores, which may open more avenues for the applications of originally non- or poor fluorescent PAHs.

| S-EPMC6329816 | biostudies-other

Fluorescent polymer cubosomes and hexosomes with aggregation-induced emission.

Project description:Fluorescent polymer cubosomes and hexosomes with aggregation-induced emission (AIE) were prepared from amphiphilic block copolymers PEG-b-PTPEMA where the hydrophobic block PTPEMA was a polymethacrylate with tetraphenylethene (TPE) as the AIE side group. Four highly asymmetric block copolymers with hydrophilic block weight ratio f PEG ≤ 20% were synthesized. Cubosomes and hexosomes with strong fluorescence emission were obtained by nanoprecipitation of polymers with f PEG < 9% in dioxane/water and THF/water systems. Their ordered internal structures were studied by electron microscopy (cryo-EM, SEM and TEM) and the X-ray scattering technique (SAXS). To elucidate the formation mechanisms of these inverted colloids, other parameters influencing the morphologies, like the water content during self-assembly and the organic solvent composition, were also investigated. This study not only inspires people to design novel building blocks for the preparation of functional cubosomes and hexosomes, but also presents the first AIE fluorescent polymer cubosome and hexosome with potential applications in bio-related fields.

| S-EPMC8179552 | biostudies-literature

A highly sensitive and selective fluorescent probe without quencher for detection of Pb<sup>2+</sup> ions based on aggregation-caused quenching phenomenon.

Project description:Lead is a highly toxic heavy metal, and various functional nucleic acid (FNA)-based biosensors have been developed for the detection of Pb2+ in environmental monitoring. However, most fluorescence biosensors that have been reported were designed on the basis of a double-labeled (fluorophore and quencher group) DNA sequence, which not only involved an inconvenient organic synthesis but also restricted their wider use in practical applications. Here, we utilized a G-rich DNA sequence as a recognition probe and conjugated fluorene (CF) to develop a fluorescence sensor without a quencher based on the aggregation-caused quenching (ACQ) effect. In the presence of Pb2+, the degree of aggregation of CF was reduced because Pb2+ induced the formation of a G-quadruplex structure of the CF-DNA probe, and the fluorescence signal increased with the concentration of Pb2+ (0-1 μM), with a limit of detection of 0.36 nM. This fluorescent probe without a quencher enables the sensitive and selective detection of Pb2+. On the basis of these advantages, the CF-DNA probe represents a promising analytical method for detecting Pb2+.

| S-EPMC9090614 | biostudies-literature

Coemissive luminescent nanoparticles combining aggregation-induced emission and quenching dyes prepared in continuous flow.

Project description:Achieving an ideal light-harvesting system at a low cost remains a challenge. Herein, we report the synthesis of a hybrid dye system based on tetraphenylene (TPE) encapsulated organic dyes in a continuous flow microreactor. The composite dye nanoparticles (NPs) are synthesized based on supramolecular self-assembly to achieve the co-emission of aggregation-induced emission dyes and aggregation-caused quenching dyes (CEAA). Numerical simulations and molecular spectroscopy were used to investigate the synthesis mechanism of the CEAA dyes. Nanoparticles of CEAA dyes provide a platform for efficient cascade Förster resonance energy transfer (FRET). Composite dye nanoparticles of TPE and Nile red (NiR) are synthesized for an ideal light-harvesting system using coumarin 6 (C-6) as an energy intermediate. The light-harvesting system has a considerable red-shift distance (~126 nm), high energy-transfer efficiency (ΦET) of 99.37%, and an antenna effect of 26.23. Finally, the versatility of the preparation method and the diversity of CEAA dyes are demonstrated.

| S-EPMC9562343 | biostudies-literature

Achieving very bright mechanoluminescence from purely organic luminophores with aggregation-induced emission by crystal design.

Project description:Although bright organic mechanoluminescence (ML) has been observed for a few luminophores with aggregation-induced emission (AIE), details of the positive effect of AIE on ML performance remain unclear and a feasible design principle for AIE-ML compounds has not yet been presented. Herein, an effective strategy for the molecular design of efficient AIE-ML materials is demonstrated, based on tetraphenylethene (TPE) building blocks with formyl substituents, which yield non-centrosymmetric crystal structures with prominent piezoelectric properties for molecular excitation combined with AIE features for intense emission. Following this approach, three AIE-active compounds have been developed and are found to show unique ML characteristics. Furthermore, the results of single crystal X-ray analysis and density functional theory (DFT) calculations suggest that the ML performance would probably be further enhanced by creating molecules with larger dipolar moments and enhanced AIE properties.

| S-EPMC6020548 | biostudies-literature

Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene.

Project description:Background: Diarylethenes are well-known photochromic compounds, which undergo cyclization and cycloreversion reactions between open- and closed-ring isomers. Recently, diarylethene derivatives with photoswitchable fluorescent properties were prepared. They are applicable for fluorescence imaging including bio-imaging. On the other hand, a new system called "excited state intramolecular proton transfer (ESIPT)" is reported. In the system, absorption and emission bands are largely separated due to the proton transfer, hence it showed strong fluorescence even in the crystalline state. We aimed to construct the photochromic system incorporating the ESIPT mechanism. Results: A diarylethene incorporating a fluorescent moiety that exhibit ESIPT behavior was prepared. The ESIPT is one of the examples which express the mechanisms of aggregation-induced emission (AIE). This compound emits orange fluorescence with a large Stokes shift derived from ESIPT in aprotic solvents such as THF or hexane, while it exhibits only a photochromic reaction in protic solvents such as methanol. In addition, it shows turn-off type fluorescence switching in an aprotic solvent and in crystals. The fluorescence is quenched as the content of closed-ring isomers increases upon UV light irradiation. Conclusions: A diarylethene containing an ESIPT functional group was prepared. It showed fluorescent turn-off behavior during photochromism in aprotic solvents as well as in crystalline state upon UV light irradiation. Furthermore, it showed AIE in THF/water mixtures with blue-shift of the emission.

| S-EPMC6774079 | biostudies-literature

Demonstrating Biological Fate of Nanoparticle-Loaded Dissolving Microneedles with Aggregation-Caused Quenching Probes: Influence of Application Sites.

Project description:Integrating dissolving microneedles (DMNs) and nanocarriers (NC) holds great potential in transdermal drug delivery because it can simultaneously overcome the stratum corneum barrier and achieve efficient and controlled drug delivery. However, different skin sites with different thicknesses and compositions can affect the transdermal diffusion of NC-loaded DMNs. There are few reports on the biological fate (especially transdermal diffusion) of NC-loaded DMNs, and inaccurate bioimaging information of intact NC limits the accurate understanding of the in vivo fate of NC-loaded DMNs. The aggregation-caused quenching (ACQ) probes P4 emitted intense fluorescence signals in intact NC while quenched after the degradation of NC, had been demonstrated the feasibility of label intact NC. In this study, P4 was loaded in solid lipid nanoparticles (SLNs), and further encapsulated into DMNs, to track the transdermal diffusion of SLNs delivered at different skin sites. The results showed that SLNs had excellent stability after being loaded into DMNs with no significant changes in morphology and fluorescence properties. The in vivo live and ex vivo imaging showed that the transdermal diffusion rate of NC-loaded DMNs was positively correlated with skin thickness, with the order ear > abdomen > back. In conclusion, this study confirmed the site-dependency of transdermal diffusion in NC-loaded DMNs.

| S-EPMC9867466 | biostudies-literature

Selectively Light-up Detection of Phosgene with an Aggregation-Induced Emission-Based Fluorescent Sensor.

Project description:Phosgene, a widely used but highly toxic substance, may pose a serious risk to public safety and health because of the potential abuse and possible accidental leakage. Consequently, it is of great significance to develop a rapid, reliable, and sensitive detection method for this noxious agent. In this work, an aggregation-induced emission-based sensor, 3,6-bis(1,2,2-triphenylvinyl)benzene-1,2-diamine (DATPE), has been rationally designed for detecting phosgene by conjugation of o-phenylenediamine (OPD) core as the reactive recognition moiety decorated with two peripheral triphenylethylene (TPE) units. A light-up fluorescence response is achieved by the fast cyclization reaction of OPD part and phosgene along with the formation of 2-imidazolidinone ring, thus inhibiting the intramolecular charge transfer quenching process in the sensor. Moreover, an easy-to-use test paper with DATPE is fabricated for onsite visual detection of phosgene in the gas phase even at a concentration of as low as 0.1 ppm.

| S-EPMC6941368 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data