Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Quinoline-containing diarylethenes: bridging between turn-on fluorescence, RGB switching and room temperature phosphorescence† † Electronic supplementary information (ESI) available: Experimental details and spectral data. See DOI: 10.1039/c9sc05697a

ABSTRACT: Simple structural modifications using oxidation and methylation of a quinoline-containing diarylethene result in dramatic variation of photophysical properties. Turn-on fluorescence, room temperature phosphorescence (RTP) and red-green-blue (RGB) switching were achieved in three different related compounds. Photoswitchable diarylethenes (DAEs) that exhibit turn-on fluorescence are in high demand for super-resolution microscopy, and the development of purely organic phosphorescent materials in the amorphous state is attractive but challenging. The findings reported here provide a novel toolkit for designing turn-on fluorescence DAEs for super-resolution microscopy and extending the scope of amorphous RTP materials. More importantly, we bridge between these two fundamentally significant photochemical and photophysical phenomena, and reveal structure–property relationships between DAE photochromism and RTP. Simple structural modifications using oxidation and methylation of a quinoline-containing diarylethene result in dramatic variation of photophysical properties.

SUBMITTER: Xu Z

PROVIDER: S-EPMC8157510 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Turn-on mode diarylethenes for bioconjugation and fluorescence microscopy of cellular structures.

Project description:The use of photoswitchable fluorescent diarylethenes (fDAEs) as protein labels in fluorescence microscopy and nanoscopy has been limited by labeling inhomogeneity and the need for ultraviolet light for fluorescence activation (on-switching). To overcome these drawbacks, we prepared "turn-on mode" fDAEs featuring thienyl substituents, multiple polar residues, and a reactive maleimide group in the core structure. Conjugates with antibodies and nanobodies displayed complete on-switching and excitation with violet (405 nm) and yellow-green (<565 nm) light, respectively. Besides, they afforded high signal-to-noise ratios and low unspecific labeling in fluorescence imaging. Irradiation with visible light at 532 nm or 561 nm led to transient on-off switching ("blinking") of the fDAEs of double-labeled nanobodies so that nanoscale superresolution images were readily attained through switching and localization of individual fluorophores.

| S-EPMC8040663 | biostudies-literature

Fluorescence On/Off Switching in Nanoparticles Consisting of Two Types of Diarylethenes.

Project description:Single- and double-component nanoparticles consisting of two types of diarylethenes, 1,2-bis(3-methyl-5-phenyl-2-thienyl)perfluorocyclopentene (1a) and 1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene (2a), were fabricated by a reprecipitation method. Nanoparticles consisting of 1a exhibited orange or green fluorescence depending on the fabrication condition and did not undergo any photocyclization reaction. On the other hand, nanoparticles consisting of 2a underwent photoreversible photochromic reactions upon alternating irradiation with ultraviolet and visible light. Nanoparticles consisting of 1a and 2a exhibited fluorescence on/off switching with rapid switching speed and high on/off contrast, accompanying the photochromic reactions of 2a. The dependence of fluorescence on/off switching properties on Förster distance and molar fraction was observed and quantitatively evaluated by a simplified model.

| S-EPMC6641326 | biostudies-literature

Reversible switching from fluorescence to room temperature phosphorescence amplified by exciton-vibration coupling through pressure-induced tiny packing changes.

Project description:Investigating the impact of exciton-vibration coupling (EC) of molecular aggregates on regulating the excited-state dynamics and controlling room temperature phosphorescence (RTP) emissions is crucial and challenging. We designed and synthesized ArBFO molecules and cultured two crystals with similar molecular packing and completely different luminescent mechanisms from B-form fluorescence to G-form RTP. The mechanism study combining measurement of photophysical properties, time-resolved fluorescence analysis, X-ray diffraction analysis, and theoretical calculations shows that tiny changes in molecular stacking amplify the EC value from B-form to G-form H-aggregates. The larger EC value accelerates the ISC process and suppresses the radiative singlet decay. Meanwhile, the stronger intermolecular interaction restricts non-radiative transitions. All of these facilitate green RTP emission in G-form aggregates. When treated with pressure-heating cycles, the transformation between B-form and G-form aggregates leads to a reversible blue fluorescence/green RTP switch with good reproducibility and photostability. Moreover, their potential in multi-level information encryption and anti-counterfeiting application has been well demonstrated. The results of this research deepen the understanding of the effect of aggregation on the luminescence mechanism and provide a new design guidance for developing smart materials with good performance.

| S-EPMC11317904 | biostudies-literature

Switching Singlet Exciton to Triplet for Efficient Pure Organic Room-Temperature Phosphorescence by Rational Molecular Design.

Project description:The design and regulation of phosphors are attractive but challenging because of the spin-forbidden intersystem crossing (ISC) process. Here, a new perspective on the enhancement of the ISC is proposed and demonstrated. Different from current strategies, the ISC yield (ΦISC) is enhanced by decreasing the fluorescence radiative transition rate constant (kF) via rational molecular designing rather than boosting the spin-orbit coupling by decorating the molecular skeleton with a heavy atom, heteroatom, or carbonyl. The kF of the designed molecule in this case is associated with the substituent position of the methoxy group, which alters the distribution of the front orbitals. The S0 → S1 transition of these compounds evolves from a bright state to a dark state gradually with the variation of the substituent position, accompanied by the decrease of kF and increase of ΦISC. The fluorescence emission is switched to phosphorescence emission successfully by regulating the kF. This work provides an alternative strategy to design efficient room-temperature phosphorescence material.

| S-EPMC10369410 | biostudies-literature

Controlling the fluorescence and room-temperature phosphorescence behaviour of carbon nanodots with inorganic crystalline nanocomposites.

Project description:There is a significant drive to identify alternative materials that exhibit room temperature phosphorescence for technologies including bio-imaging, photodynamic therapy and organic light-emitting diodes. Ideally, these materials should be non-toxic and cheap, and it will be possible to control their photoluminescent properties. This was achieved here by embedding carbon nanodots within crystalline particles of alkaline earth carbonates, sulphates and oxalates. The resultant nanocomposites are luminescent and exhibit a bright, sub-second lifetime afterglow. Importantly, the excited state lifetimes, and steady-state and afterglow colours can all be systematically controlled by varying the cations and anions in the host inorganic phase, due to the influence of the cation size and material density on emissive and non-emissive electronic transitions. This simple strategy provides a flexible route for generating materials with specific, phosphorescent properties and is an exciting alternative to approaches relying on the synthesis of custom-made luminescent organic molecules.

| S-EPMC6331607 | biostudies-literature

Modulating Room-Temperature Phosphorescence-To-Phosphorescence Mechanochromism by Halogen Exchange.

Project description:Modulating the stimulus-responsiveness of a luminescent crystal is challenging owing to the complex interdependent nature of its controlling factors, such as molecular structure, molecular conformation, crystal packing, optical properties, and amorphization behavior. Herein, we demonstrate a halogen-exchange approach that disentangles this problem, thereby realizing the modulation of room-temperature phosphorescence-to-phosphorescence mechanochromism. Replacing the bromine atoms in a brominated thienyl diketone with chlorine atoms afforded isostructural crystals; i.e., molecules with different halogen atoms exhibited the same molecular conformation and crystal packing. Consequently, amorphization behavior toward mechanical stimulation was also the same, and the phosphorescence of amorphous states originated from the same conformer of each diketone. In contrast, the phosphorescence properties of each conformer were modulated differently, which is ascribable to heavy atom effects, resulting in the modulation of the mechanochromism. Thus, halogen exchange is a promising approach for modulating the stimulus-responsive photofunctions of crystals involving spin-forbidden processes.

| S-EPMC8793743 | biostudies-literature

Room Temperature Phosphorescence Emission From Multi-States.

Project description:Organic room temperature phosphorescence (RTP) materials have received considerable attention due to their fascinating photophysical properties. During the past decade, various organic luminogens exhibiting RTP emission in solid states were reported. However, the phosphorescence emission of organic compounds can hardly be observed in their solutions at room temperature. Herein, we reported two fluorene derivatives that can emit RTP in degassed organic solvents, polymer doped film, and crystalline states. Furthermore, those RTP luminogens emitted different colors with different phosphorescence lifetimes in multi-states. These results indicated that the phosphorescence performance can be adjusted flexibly in different condensed states. To our knowledge, this is the first example possessing diverse organic RTP at multi-states, including solution state.

| S-EPMC8847601 | biostudies-literature

A building-block design for enhanced visible-light switching of diarylethenes.

Project description:Current development of light-responsive materials and technologies imposes an urgent demand on visible-light photoswitching on account of its mild excitation with high penetration ability and low photo-toxicity. However, complicated molecular design and laborious synthesis are often required for visible-light photoswitch, especially for diarylethenes. Worse still, a dilemma is encountered as the visible-light excitation of the diarylethene is often achieved at the expense of photochromic performances. To tackle these setbacks, we introduce a building-block design strategy to achieve all-visible-light photochromism with the triplet-sensitization mechanism. The simply designed diarylethene system is constructed by employing a sensitizer building-block with narrow singlet-triplet energy gap (ΔEST) to a diarylethene building-block. A significant improvement on the photochromic efficiency is obtained as well as an enhanced photo-fatigue resistance over those under UV irradiation. The balance between the visible-light excitation and decent photochromism is thus realized, promoting a guiding principle for the visible-light photochromism.

| S-EPMC6748945 | biostudies-literature

Purely Organic Microparticles Showing Ultralong Room Temperature Phosphorescence.

Project description:Currently, organic phosphorescent particles are heavily used in sensing and imaging. Up to now, most of these particles contain poisonous and/or expensive metal complexes. Environmentally friendly systems are therefore highly desired. A purely amorphous system consisting of poly(methyl methacrylate) particles with incorporated N,N,N',N'-tetrakis(4-carboxyphenyl)benzidine emitter molecules is presented in this work. Single particles with sizes between 400 and 840 nm show-depending on the environment-bright fluorescence and phosphorescence. The latter is observed when oxygen is not in the proximity of the emitting dye molecules. These particles can scavenge singlet oxygen, which is produced during the photoexcitation process, by incorporating it into the polymer matrix. This renders their use to be unharmful for the surrounding matter with possible application in marking schemes for living bodies.

| S-EPMC8158833 | biostudies-literature

A 7-Hydroxybenzoxazinone-Containing Fluorescence Turn-On Probe for Biothiols and Its Bioimaging Applications.

Project description:In this work, a novel 7-hydroxybenzoxazinone-based fluorescent probe (PBD) for the selective sensing of biothiols is reported. Upon treatment with biothiols, PBD shows a strong fluorescence enhancement (up to 70-fold) and a large Stokes shift (155 nm). Meanwhile, this probe exhibits high resistance to interference from other amino acids and competing species. PBD features good linearity ranges with a low detection limit of 14.5 nM for glutathione (GSH), 17.5 nM for cysteine (Cys), and 80.0 nM for homocysteine (Hcy), respectively. Finally, the potential utility of this probe for biothiol sensing in living HeLa cells is demonstrated.

| S-EPMC6749190 | 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